diff --git a/apps/edr-freight-api/src/migrations/3370000000000-SupportHelpInlineMedia.ts b/apps/edr-freight-api/src/migrations/3370000000000-SupportHelpInlineMedia.ts
new file mode 100644
index 000000000..3301056e4
--- /dev/null
+++ b/apps/edr-freight-api/src/migrations/3370000000000-SupportHelpInlineMedia.ts
@@ -0,0 +1,91 @@
+import { MigrationInterface, QueryRunner } from "typeorm";
+
+/**
+ * Folds each help section's `media[]` array into its markdown body.
+ *
+ * Attachments used to hang off the section as a separate list, rendered after
+ * the text — which meant an author could not put a picture next to the sentence
+ * it illustrates, and had two different places to manage media. They are now
+ * embedded with markdown's image syntax, and the renderer picks `<img>` or
+ * `<video>` from the file extension.
+ *
+ * Existing entries are converted rather than dropped: an uploaded object
+ * becomes `![caption](minio:<key>)`, and a shipped asset path or external URL
+ * is kept verbatim. Sections are left alone once they have no `media` key, so
+ * re-running does nothing.
+ */
+interface LegacyMedia {
+  src: string;
+  caption?: string | null;
+}
+
+interface LegacySection {
+  id: string;
+  heading: string;
+  body: string;
+  media?: LegacyMedia[];
+}
+
+/** Uploaded objects are stored as keys; the `minio:` ref is signed on read. */
+function toMarkdown(item: LegacyMedia): string {
+  const isStoredObject = !/^(https?:\/\/|\/)/.test(item.src);
+  const target = isStoredObject ? `minio:${item.src}` : item.src;
+  return `![${item.caption ?? ""}](${target})`;
+}
+
+export class SupportHelpInlineMedia3370000000000 implements MigrationInterface {
+  name = "SupportHelpInlineMedia3370000000000";
+
+  public async up(queryRunner: QueryRunner): Promise<void> {
+    const rows: {
+      id: string;
+      version: number;
+      payload: { sections?: LegacySection[] } & Record<string, unknown>;
+    }[] = await queryRunner.query(`
+      SELECT id, version, payload
+      FROM freight.support_documents
+      WHERE slug = 'HELP'
+    `);
+
+    for (const row of rows) {
+      const sections = row.payload.sections ?? [];
+      if (!sections.some((section) => section.media !== undefined)) continue;
+
+      const payload = {
+        ...row.payload,
+        sections: sections.map(({ media, ...section }) => {
+          const embeds = (media ?? []).map(toMarkdown);
+          return {
+            ...section,
+            body: [section.body, ...embeds].filter(Boolean).join("\n\n"),
+          };
+        }),
+      };
+      const version = row.version + 1;
+
+      await queryRunner.query(
+        `UPDATE freight.support_documents
+         SET payload = $1::jsonb, version = $2, updated_at = now()
+         WHERE id = $3`,
+        [JSON.stringify(payload), version, row.id],
+      );
+
+      await queryRunner.query(
+        `INSERT INTO freight.support_document_versions
+           (document_id, version, payload, actor_id, note)
+         VALUES ($1, $2, $3::jsonb, NULL, $4)`,
+        [
+          row.id,
+          version,
+          JSON.stringify(payload),
+          "Moved attachments inline into the section text",
+        ],
+      );
+    }
+  }
+
+  /** Not reversible — see the note on SupportHelpSections3360000000000. */
+  public async down(): Promise<void> {
+    // no-op
+  }
+}
diff --git a/apps/edr-freight-api/src/modules/support-content/dto/support-content.dto.ts b/apps/edr-freight-api/src/modules/support-content/dto/support-content.dto.ts
index fdfffe8be..64b5bfcb2 100644
--- a/apps/edr-freight-api/src/modules/support-content/dto/support-content.dto.ts
+++ b/apps/edr-freight-api/src/modules/support-content/dto/support-content.dto.ts
@@ -1,10 +1,9 @@
-import { SUPPORT_MEDIA_PREFIX, SupportDocSlug } from "@edr/types";
+import { SupportDocSlug } from "@edr/types";
 import { ApiProperty, ApiPropertyOptional } from "@nestjs/swagger";
 import { Type } from "class-transformer";
 import {
   ArrayMaxSize,
   IsArray,
-  IsIn,
   IsObject,
   IsOptional,
   IsString,
@@ -28,17 +27,6 @@ const LINK_PATTERN = /^(https?:\/\/|mailto:|tel:|\/)/;
 const LINK_MESSAGE =
   "$property must start with http(s)://, mailto:, tel: or /";
 
-/**
- * A media source is either an uploaded MinIO object key, a same-origin path, or
- * an https URL. Anything else — notably `javascript:` — is refused, since this
- * value lands in an `<img>`/`<video>` src.
- */
-const MEDIA_SRC_PATTERN = new RegExp(
-  `^(https?:\\/\\/|\\/|${SUPPORT_MEDIA_PREFIX.replace("/", "\\/")})`,
-);
-const MEDIA_SRC_MESSAGE =
-  `$property must be an uploaded ${SUPPORT_MEDIA_PREFIX} key, a /path, or an http(s):// URL`;
-
 /* ------------------------------- CONTACT ------------------------------- */
 
 export class PortalSupportContactDto {
@@ -208,58 +196,6 @@ export class PortalFaqContentDto {
 
 /* --------------------------------- HELP -------------------------------- */
 
-export class PortalMediaDto {
-  @ApiPropertyOptional({ description: "Stable id; generated when omitted" })
-  @IsOptional()
-  @IsString()
-  @MaxLength(64)
-  id?: string;
-
-  @ApiProperty({ enum: ["image", "video"] })
-  @IsIn(["image", "video"])
-  kind!: "image" | "video";
-
-  @ApiProperty({
-    description: `An uploaded ${SUPPORT_MEDIA_PREFIX} key, a same-origin /path, or an https:// URL`,
-  })
-  @IsString()
-  @Matches(MEDIA_SRC_PATTERN, { message: MEDIA_SRC_MESSAGE })
-  @MaxLength(500)
-  src!: string;
-
-  @ApiPropertyOptional({ nullable: true })
-  @IsOptional()
-  @IsString()
-  @MaxLength(300)
-  caption?: string | null;
-}
-
-export class PortalHelpSectionDto {
-  @ApiPropertyOptional({ description: "Stable id; generated when omitted" })
-  @IsOptional()
-  @IsString()
-  @MaxLength(64)
-  id?: string;
-
-  @ApiProperty()
-  @IsString()
-  @MinLength(1)
-  @MaxLength(200)
-  heading!: string;
-
-  @ApiProperty({ description: "Markdown" })
-  @IsString()
-  @MaxLength(20_000)
-  body!: string;
-
-  @ApiProperty({ type: [PortalMediaDto] })
-  @IsArray()
-  @ArrayMaxSize(12)
-  @ValidateNested({ each: true })
-  @Type(() => PortalMediaDto)
-  media!: PortalMediaDto[];
-}
-
 export class PortalHelpContentDto {
   @ApiProperty()
   @IsString()
@@ -272,12 +208,16 @@ export class PortalHelpContentDto {
   @MaxLength(500)
   subtitle!: string;
 
-  @ApiProperty({ type: [PortalHelpSectionDto] })
+  /**
+   * Same section shape as the legal documents — images and videos live inside
+   * the markdown, so a help section needs nothing the others do not have.
+   */
+  @ApiProperty({ type: [PortalDocSectionDto] })
   @IsArray()
   @ArrayMaxSize(40)
   @ValidateNested({ each: true })
-  @Type(() => PortalHelpSectionDto)
-  sections!: PortalHelpSectionDto[];
+  @Type(() => PortalDocSectionDto)
+  sections!: PortalDocSectionDto[];
 }
 
 /* ------------------------------- request ------------------------------- */
diff --git a/apps/edr-freight-api/src/modules/support-content/support-content.service.spec.ts b/apps/edr-freight-api/src/modules/support-content/support-content.service.spec.ts
index 9e6281762..d1d72b397 100644
--- a/apps/edr-freight-api/src/modules/support-content/support-content.service.spec.ts
+++ b/apps/edr-freight-api/src/modules/support-content/support-content.service.spec.ts
@@ -131,7 +131,8 @@ describe("SupportContentService.getBundle", () => {
     // findAll returns only CONTACT, so HELP falls back to the defaults — which
     // is itself worth asserting: an unseeded row must not break the page.
     const bundle = await service.getBundle();
-    expect(bundle.help.sections[0].media[0].src).toBe(
+    // A shipped asset path is not a stored object, so nothing is signed.
+    expect(bundle.help.sections[0].body).toContain(
       "/assets/edr-portal-guide.webm",
     );
     expect(minio.getSignedUrl).not.toHaveBeenCalled();
@@ -141,10 +142,9 @@ describe("SupportContentService.getBundle", () => {
       sections: [
         {
           ...help.sections[0],
-          body: "See ![diagram](minio:support-content/d.png) below.",
-          media: [
-            { id: "m1", kind: "image" as const, src: "support-content/a.png" },
-          ],
+          body:
+            "See ![diagram](minio:support-content/d.png) and " +
+            "![clip](minio:support-content/c.mp4).",
         },
       ],
     };
@@ -154,14 +154,14 @@ describe("SupportContentService.getBundle", () => {
       help: withUpload,
     });
 
-    expect(signed.help.sections[0].media[0].src).toBe(
-      "https://minio.test/support-content/a.png?sig=x",
-    );
     expect(signed.help.sections[0].body).toContain(
       "https://minio.test/support-content/d.png?sig=x",
     );
+    expect(signed.help.sections[0].body).toContain(
+      "https://minio.test/support-content/c.mp4?sig=x",
+    );
     // The stored copy must never be mutated into a URL — that is what would rot.
-    expect(withUpload.sections[0].media[0].src).toBe("support-content/a.png");
+    expect(withUpload.sections[0].body).toContain("minio:support-content/d.png");
   });
 });
 
@@ -176,40 +176,33 @@ describe("validatePayload", () => {
     }
   });
 
-  const sectionWithMedia = (src: string) => ({
+  const sectionWithBody = (body: string) => ({
     ...help,
-    sections: [{ ...help.sections[0], media: [{ kind: "video", src }] }],
+    sections: [{ ...help.sections[0], body }],
   });
 
-  it("rejects a javascript: media source", () => {
-    // The markdown renderer drops raw HTML, so src attributes like this one are
-    // the only place a script URL could still execute.
-    expect(() =>
-      validatePayload("HELP", sectionWithMedia("javascript:alert(1)")),
-    ).toThrow(BadRequestException);
-  });
-
-  it("accepts an uploaded key, a rooted path and an https URL", () => {
-    for (const src of [
-      "support-content/9f1c.png",
-      "/assets/edr-portal-guide.webm",
-      "https://cdn.example.com/clip.mp4",
+  it("stores embedded media as refs, whatever the scheme", () => {
+    // Media now lives in the markdown, so the API no longer validates its URL
+    // scheme — the portal's renderer does, by dropping anything that is not
+    // http(s)/mailto/tel/relative. These all persist fine.
+    for (const body of [
+      "![](minio:support-content/9f1c.png)",
+      "![](/assets/edr-portal-guide.webm)",
+      "![](https://cdn.example.com/clip.mp4)",
     ]) {
-      expect(() => validatePayload("HELP", sectionWithMedia(src))).not.toThrow();
+      expect(() => validatePayload("HELP", sectionWithBody(body))).not.toThrow();
     }
   });
 
-  it("rejects a media kind that is neither image nor video", () => {
+  it("rejects a section body past the cap", () => {
     expect(() =>
-      validatePayload("HELP", {
-        ...help,
-        sections: [
-          {
-            ...help.sections[0],
-            media: [{ kind: "pdf", src: "support-content/a.pdf" }],
-          },
-        ],
-      }),
+      validatePayload("HELP", sectionWithBody("x".repeat(20_001))),
+    ).toThrow(BadRequestException);
+  });
+
+  it("rejects an unknown property, which is how a stale payload is caught", () => {
+    expect(() =>
+      validatePayload("HELP", { ...help, channels: [] }),
     ).toThrow(BadRequestException);
   });
 
diff --git a/apps/edr-freight-api/src/modules/support-content/support-content.service.ts b/apps/edr-freight-api/src/modules/support-content/support-content.service.ts
index edc4f2bce..11099ae55 100644
--- a/apps/edr-freight-api/src/modules/support-content/support-content.service.ts
+++ b/apps/edr-freight-api/src/modules/support-content/support-content.service.ts
@@ -51,9 +51,6 @@ const MEDIA_REF = new RegExp(
   "g",
 );
 
-/** Anything not already a URL or a rooted path is a MinIO object key. */
-const isObjectKey = (src: string) => !/^(https?:\/\/|\/)/.test(src);
-
 @Injectable()
 export class SupportContentService {
   constructor(
@@ -127,9 +124,9 @@ export class SupportContentService {
   }
 
   /**
-   * Swaps every stored MinIO reference for a freshly signed URL: attachment
-   * `src` keys, and `minio:<key>` references embedded in markdown by the
-   * editor's image button.
+   * Swaps every `minio:<key>` reference embedded in the copy for a freshly
+   * signed URL. Media lives inside the markdown, so this one pass covers every
+   * document.
    *
    * Each distinct key is signed once per request, and a signing failure
    * degrades to MinIO's public URL rather than failing the whole page (see
@@ -140,12 +137,6 @@ export class SupportContentService {
   ): Promise<PortalContentBundle> {
     const keys = new Set<string>();
 
-    for (const section of bundle.help.sections ?? []) {
-      for (const item of section.media ?? []) {
-        if (isObjectKey(item.src)) keys.add(item.src);
-      }
-    }
-
     const collect = (value: unknown): void => {
       if (typeof value === "string") {
         for (const match of value.matchAll(MEDIA_REF)) keys.add(match[1]);
@@ -183,15 +174,7 @@ export class SupportContentService {
       return value;
     };
 
-    const resolved = rewrite(bundle) as PortalContentBundle;
-
-    for (const section of resolved.help.sections ?? []) {
-      for (const item of section.media ?? []) {
-        if (isObjectKey(item.src)) item.src = signed.get(item.src) ?? item.src;
-      }
-    }
-
-    return resolved;
+    return rewrite(bundle) as PortalContentBundle;
   }
 
   /** Admin list — metadata only, no payloads. */
@@ -339,13 +322,7 @@ function withGeneratedIds(
   switch (slug) {
     case "HELP": {
       const help = payload as PortalHelpContent;
-      return {
-        ...help,
-        sections: help.sections.map((section) => ({
-          ...withId(section),
-          media: (section.media ?? []).map(withId),
-        })),
-      };
+      return { ...help, sections: help.sections.map(withId) };
     }
     case "FAQ": {
       const faq = payload as PortalFaqContent;
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/AccordionRow.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/AccordionRow.tsx
deleted file mode 100644
index 309bdb34c..000000000
--- a/apps/edr-freight-web/backoffice/src/pages/portal_content/AccordionRow.tsx
+++ /dev/null
@@ -1,95 +0,0 @@
-import { Accordion, ActionIcon, Center, Group, Text, Tooltip } from "@mantine/core";
-import { ChevronDown, ChevronUp, Trash2 } from "lucide-react";
-import type { ReactNode } from "react";
-
-interface AccordionRowProps {
-  value: string;
-  /** Collapsed summary — the heading, question or card title. */
-  title: string;
-  /** Small dimmed line under the title, e.g. a body excerpt. */
-  subtitle?: string;
-  index: number;
-  length: number;
-  onMove: (delta: number) => void;
-  onRemove: () => void;
-  children: ReactNode;
-}
-
-/**
- * One collapsible item with reorder and delete controls in its header.
- *
- * Collapsing is the point: a legal document has fifteen sections and the FAQ
- * seventeen answers, and rendering every textarea expanded turned each tab into
- * an unnavigable mile of boxes. Collapsed, the tab reads as the list of
- * headings the customer actually sees.
- *
- * The buttons sit outside `Accordion.Control` so clicking one does not also
- * toggle the panel.
- */
-export function AccordionRow({
-  value,
-  title,
-  subtitle,
-  index,
-  length,
-  onMove,
-  onRemove,
-  children,
-}: AccordionRowProps) {
-  return (
-    <Accordion.Item value={value}>
-      <Center>
-        <Accordion.Control>
-          <div style={{ minWidth: 0 }}>
-            <Text fw={500} truncate>
-              {title || <Text span c="dimmed">(untitled)</Text>}
-            </Text>
-            {subtitle && (
-              <Text size="xs" c="dimmed" truncate>
-                {subtitle}
-              </Text>
-            )}
-          </div>
-        </Accordion.Control>
-
-        <Group gap={2} wrap="nowrap" pr="sm">
-          <Tooltip label="Move up">
-            <ActionIcon
-              variant="subtle"
-              color="gray"
-              disabled={index === 0}
-              onClick={() => onMove(-1)}
-            >
-              <ChevronUp size={16} />
-            </ActionIcon>
-          </Tooltip>
-          <Tooltip label="Move down">
-            <ActionIcon
-              variant="subtle"
-              color="gray"
-              disabled={index === length - 1}
-              onClick={() => onMove(1)}
-            >
-              <ChevronDown size={16} />
-            </ActionIcon>
-          </Tooltip>
-          <Tooltip label="Remove">
-            <ActionIcon variant="subtle" color="red" onClick={onRemove}>
-              <Trash2 size={16} />
-            </ActionIcon>
-          </Tooltip>
-        </Group>
-      </Center>
-
-      <Accordion.Panel>{children}</Accordion.Panel>
-    </Accordion.Item>
-  );
-}
-
-/** First line of a markdown body, for an accordion subtitle. */
-export function excerpt(markdown: string, max = 90): string {
-  const line = markdown.replace(/[#*`>-]/g, "").trim().split("\n")[0] ?? "";
-  return line.length > max ? `${line.slice(0, max)}…` : line;
-}
-
-export default AccordionRow;
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/DocumentRail.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/DocumentRail.tsx
new file mode 100644
index 000000000..a5cea78b8
--- /dev/null
+++ b/apps/edr-freight-web/backoffice/src/pages/portal_content/DocumentRail.tsx
@@ -0,0 +1,163 @@
+import { ActionIcon, Box, Button, Group, Stack, Text, Tooltip } from "@mantine/core";
+import { ChevronDown, ChevronUp, Plus } from "lucide-react";
+
+export interface RailItem {
+  id: string;
+  label: string;
+  /** Renders as a small caps heading above the items that follow it. */
+  heading?: string;
+  /** Nested one level (an FAQ question under its group). */
+  indented?: boolean;
+}
+
+interface DocumentRailProps {
+  items: RailItem[];
+  selectedId: string | null;
+  onSelect: (id: string) => void;
+  onMove: (id: string, delta: number) => void;
+  /** Whether this row can move in the given direction. */
+  canMove: (id: string, delta: number) => boolean;
+  addLabel: string;
+  onAdd: () => void;
+  emptyLabel: string;
+}
+
+/**
+ * The list of pages that make up a document, and the only navigation on the
+ * tab. Replaces the accordion stack: a public officer editing the privacy
+ * policy sees fifteen page names, clicks one, and edits it — instead of
+ * scrolling a mile of open text boxes trying to find the right one.
+ *
+ * Reorder arrows appear only on the selected row, so the resting state is a
+ * clean list rather than fifteen rows of buttons.
+ */
+export function DocumentRail({
+  items,
+  selectedId,
+  onSelect,
+  onMove,
+  canMove,
+  addLabel,
+  onAdd,
+  emptyLabel,
+}: DocumentRailProps) {
+  return (
+    <Stack
+      gap={4}
+      p="sm"
+      style={{
+        width: 280,
+        flexShrink: 0,
+        alignSelf: "flex-start",
+        background: "#FFFFFF",
+        border: "1px solid var(--mantine-color-gray-2)",
+        borderRadius: "var(--mantine-radius-lg)",
+      }}
+    >
+      {items.length === 0 && (
+        <Text size="sm" c="dimmed" p="sm">
+          {emptyLabel}
+        </Text>
+      )}
+
+      {items.map((item) => {
+        const selected = item.id === selectedId;
+
+        return (
+          <Box key={item.id}>
+            {item.heading && (
+              <Text
+                size="xs"
+                fw={700}
+                c="dimmed"
+                tt="uppercase"
+                mt="sm"
+                mb={4}
+                px="xs"
+                style={{ letterSpacing: "0.04em" }}
+              >
+                {item.heading}
+              </Text>
+            )}
+
+            <Group
+              gap={4}
+              wrap="nowrap"
+              px="xs"
+              py={6}
+              ml={item.indented ? "sm" : 0}
+              onClick={() => onSelect(item.id)}
+              style={{
+                borderRadius: "var(--mantine-radius-sm)",
+                cursor: "pointer",
+                background: selected
+                  ? "var(--mantine-primary-color-light)"
+                  : "transparent",
+              }}
+            >
+              <Text
+                size="sm"
+                fw={selected ? 600 : 400}
+                truncate
+                style={{ flex: 1, minWidth: 0 }}
+              >
+                {item.label || (
+                  <Text span c="dimmed" size="sm">
+                    Untitled
+                  </Text>
+                )}
+              </Text>
+
+              {selected && (
+                <Group gap={0} wrap="nowrap">
+                  <Tooltip label="Move up">
+                    <ActionIcon
+                      size="sm"
+                      variant="subtle"
+                      color="gray"
+                      disabled={!canMove(item.id, -1)}
+                      onClick={(e) => {
+                        e.stopPropagation();
+                        onMove(item.id, -1);
+                      }}
+                    >
+                      <ChevronUp size={14} />
+                    </ActionIcon>
+                  </Tooltip>
+                  <Tooltip label="Move down">
+                    <ActionIcon
+                      size="sm"
+                      variant="subtle"
+                      color="gray"
+                      disabled={!canMove(item.id, 1)}
+                      onClick={(e) => {
+                        e.stopPropagation();
+                        onMove(item.id, 1);
+                      }}
+                    >
+                      <ChevronDown size={14} />
+                    </ActionIcon>
+                  </Tooltip>
+                </Group>
+              )}
+            </Group>
+          </Box>
+        );
+      })}
+
+      <Button
+        variant="subtle"
+        size="sm"
+        mt="xs"
+        leftSection={<Plus size={16} />}
+        onClick={onAdd}
+        styles={{ inner: { justifyContent: "flex-start" } }}
+        fullWidth
+      >
+        {addLabel}
+      </Button>
+    </Stack>
+  );
+}
+
+export default DocumentRail;
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/EditorPane.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/EditorPane.tsx
new file mode 100644
index 000000000..8c2602867
--- /dev/null
+++ b/apps/edr-freight-web/backoffice/src/pages/portal_content/EditorPane.tsx
@@ -0,0 +1,98 @@
+import { Box, Button, Group, Stack, Text, TextInput } from "@mantine/core";
+import { Trash2 } from "lucide-react";
+import type { ReactNode } from "react";
+
+interface EditorPaneProps {
+  /** Large borderless field at the top — the page's own name. */
+  title: string;
+  titlePlaceholder: string;
+  onTitleChange: (next: string) => void;
+  onRemove: () => void;
+  removeLabel: string;
+  children: ReactNode;
+}
+
+/**
+ * The open page. One title, one body, one Remove — everything else about the
+ * document lives in the rail, so this pane stays as close to a blank sheet as
+ * the feature set allows.
+ */
+export function EditorPane({
+  title,
+  titlePlaceholder,
+  onTitleChange,
+  onRemove,
+  removeLabel,
+  children,
+}: EditorPaneProps) {
+  return (
+    <Stack
+      gap="md"
+      p="xl"
+      style={{
+        flex: 1,
+        minWidth: 0,
+        background: "#FFFFFF",
+        border: "1px solid var(--mantine-color-gray-2)",
+        borderRadius: "var(--mantine-radius-lg)",
+      }}
+    >
+      <TextInput
+        value={title}
+        placeholder={titlePlaceholder}
+        onChange={(e) => onTitleChange(e.currentTarget.value)}
+        variant="unstyled"
+        styles={{
+          input: {
+            fontSize: "1.6rem",
+            fontWeight: 700,
+            lineHeight: 1.3,
+            height: "auto",
+            padding: 0,
+          },
+        }}
+      />
+
+      <Box
+        style={{ borderTop: "1px solid var(--mantine-color-gray-2)" }}
+        pt="md"
+      >
+        {children}
+      </Box>
+
+      <Group justify="flex-end" pt="xs">
+        <Button
+          variant="subtle"
+          color="red"
+          size="compact-sm"
+          leftSection={<Trash2 size={14} />}
+          onClick={onRemove}
+        >
+          {removeLabel}
+        </Button>
+      </Group>
+    </Stack>
+  );
+}
+
+/** Shown when a document has no pages yet. */
+export function EmptyPane({ message }: { message: string }) {
+  return (
+    <Stack
+      align="center"
+      justify="center"
+      p="xl"
+      style={{
+        flex: 1,
+        minHeight: 320,
+        background: "#FFFFFF",
+        border: "1px solid var(--mantine-color-gray-2)",
+        borderRadius: "var(--mantine-radius-lg)",
+      }}
+    >
+      <Text c="dimmed">{message}</Text>
+    </Stack>
+  );
+}
+
+export default EditorPane;
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/FaqEditor.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/FaqEditor.tsx
deleted file mode 100644
index b5a9a7fca..000000000
--- a/apps/edr-freight-web/backoffice/src/pages/portal_content/FaqEditor.tsx
+++ /dev/null
@@ -1,242 +0,0 @@
-import type { PortalFaqContent, PortalFaqGroup } from "@edr/types";
-import {
-  Accordion,
-  Badge,
-  Button,
-  Card,
-  Group,
-  Stack,
-  Switch,
-  TextInput,
-} from "@mantine/core";
-import { Plus } from "lucide-react";
-
-import { AccordionRow, excerpt } from "./AccordionRow";
-import { moveAt, newId, removeAt, replaceAt } from "./array-helpers";
-import { MarkdownEditor, MarkdownHint } from "./MarkdownEditor";
-
-interface FaqEditorProps {
-  value: PortalFaqContent;
-  onChange: (next: PortalFaqContent) => void;
-}
-
-const EMPTY_FOOTER = {
-  heading: "Still need a hand?",
-  body: "",
-  ctaLabel: "Go to Help & Support",
-  ctaTo: "/help",
-};
-
-export function FaqEditor({ value, onChange }: FaqEditorProps) {
-  const setGroups = (groups: PortalFaqGroup[]) => onChange({ ...value, groups });
-
-  const setGroup = (index: number, next: PortalFaqGroup) =>
-    setGroups(replaceAt(value.groups, index, next));
-
-  return (
-    <Stack gap="lg">
-      <Card withBorder padding="md" radius="md">
-        <Stack gap="md">
-          <TextInput
-            label="Page title"
-            value={value.title}
-            onChange={(e) =>
-              onChange({ ...value, title: e.currentTarget.value })
-            }
-          />
-          <TextInput
-            label="Subtitle"
-            value={value.subtitle}
-            onChange={(e) =>
-              onChange({ ...value, subtitle: e.currentTarget.value })
-            }
-          />
-        </Stack>
-      </Card>
-
-      <MarkdownHint />
-
-      <Accordion variant="separated" radius="md" chevronPosition="left">
-        {value.groups.map((group, groupIndex) => (
-          <AccordionRow
-            key={group.id}
-            value={group.id}
-            title={group.title}
-            subtitle={`${group.items.length} question${group.items.length === 1 ? "" : "s"}`}
-            index={groupIndex}
-            length={value.groups.length}
-            onMove={(delta) => setGroups(moveAt(value.groups, groupIndex, delta))}
-            onRemove={() => setGroups(removeAt(value.groups, groupIndex))}
-          >
-            <Stack gap="md">
-              <TextInput
-                label="Group title"
-                value={group.title}
-                onChange={(e) =>
-                  setGroup(groupIndex, {
-                    ...group,
-                    title: e.currentTarget.value,
-                  })
-                }
-              />
-
-              <Accordion variant="contained" radius="sm" chevronPosition="left">
-                {group.items.map((item, itemIndex) => (
-                  <AccordionRow
-                    key={item.id}
-                    value={item.id}
-                    title={item.question}
-                    subtitle={excerpt(item.answer, 70)}
-                    index={itemIndex}
-                    length={group.items.length}
-                    onMove={(delta) =>
-                      setGroup(groupIndex, {
-                        ...group,
-                        items: moveAt(group.items, itemIndex, delta),
-                      })
-                    }
-                    onRemove={() =>
-                      setGroup(groupIndex, {
-                        ...group,
-                        items: removeAt(group.items, itemIndex),
-                      })
-                    }
-                  >
-                    <Stack gap="md">
-                      <TextInput
-                        label="Question"
-                        value={item.question}
-                        onChange={(e) =>
-                          setGroup(groupIndex, {
-                            ...group,
-                            items: replaceAt(group.items, itemIndex, {
-                              ...item,
-                              question: e.currentTarget.value,
-                            }),
-                          })
-                        }
-                      />
-                      <MarkdownEditor
-                        label="Answer"
-                        value={item.answer}
-                        onChange={(answer) =>
-                          setGroup(groupIndex, {
-                            ...group,
-                            items: replaceAt(group.items, itemIndex, {
-                              ...item,
-                              answer,
-                            }),
-                          })
-                        }
-                      />
-                    </Stack>
-                  </AccordionRow>
-                ))}
-              </Accordion>
-
-              <Button
-                variant="subtle"
-                size="xs"
-                leftSection={<Plus size={14} />}
-                style={{ alignSelf: "flex-start" }}
-                onClick={() =>
-                  setGroup(groupIndex, {
-                    ...group,
-                    items: [
-                      ...group.items,
-                      { id: newId(), question: "New question", answer: "" },
-                    ],
-                  })
-                }
-              >
-                Add question
-              </Button>
-            </Stack>
-          </AccordionRow>
-        ))}
-      </Accordion>
-
-      <Button
-        variant="light"
-        leftSection={<Plus size={16} />}
-        style={{ alignSelf: "flex-start" }}
-        onClick={() =>
-          setGroups([
-            ...value.groups,
-            { id: newId(), title: "New group", items: [] },
-          ])
-        }
-      >
-        Add group
-      </Button>
-
-      <Card withBorder padding="md" radius="md">
-        <Stack gap="md">
-          <Group justify="space-between">
-            <Switch
-              label="Closing card"
-              checked={Boolean(value.footer)}
-              onChange={(e) =>
-                onChange({
-                  ...value,
-                  footer: e.currentTarget.checked ? EMPTY_FOOTER : null,
-                })
-              }
-            />
-            {!value.footer && <Badge variant="light" color="gray">Hidden</Badge>}
-          </Group>
-
-          {value.footer && (
-            <>
-              <TextInput
-                label="Heading"
-                value={value.footer.heading}
-                onChange={(e) =>
-                  onChange({
-                    ...value,
-                    footer: { ...value.footer!, heading: e.currentTarget.value },
-                  })
-                }
-              />
-              <MarkdownEditor
-                label="Body"
-                value={value.footer.body}
-                onChange={(body) =>
-                  onChange({ ...value, footer: { ...value.footer!, body } })
-                }
-              />
-              <Group grow>
-                <TextInput
-                  label="Button label"
-                  value={value.footer.ctaLabel}
-                  onChange={(e) =>
-                    onChange({
-                      ...value,
-                      footer: {
-                        ...value.footer!,
-                        ctaLabel: e.currentTarget.value,
-                      },
-                    })
-                  }
-                />
-                <TextInput
-                  label="Button link"
-                  description="A portal route (/help) or an https:// URL"
-                  value={value.footer.ctaTo}
-                  onChange={(e) =>
-                    onChange({
-                      ...value,
-                      footer: { ...value.footer!, ctaTo: e.currentTarget.value },
-                    })
-                  }
-                />
-              </Group>
-            </>
-          )}
-        </Stack>
-      </Card>
-    </Stack>
-  );
-}
-
-export default FaqEditor;
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/FaqWorkspace.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/FaqWorkspace.tsx
new file mode 100644
index 000000000..79029abf9
--- /dev/null
+++ b/apps/edr-freight-web/backoffice/src/pages/portal_content/FaqWorkspace.tsx
@@ -0,0 +1,227 @@
+import type { PortalFaqContent, PortalFaqGroup } from "@edr/types";
+import { Button, Group, Stack, Text, TextInput } from "@mantine/core";
+import { Plus } from "lucide-react";
+import { useEffect, useState } from "react";
+
+import { moveAt, newId, removeAt, replaceAt } from "./array-helpers";
+import { DocumentRail, type RailItem } from "./DocumentRail";
+import { EditorPane, EmptyPane } from "./EditorPane";
+import { MarkdownEditor } from "./MarkdownEditor";
+
+interface FaqWorkspaceProps {
+  value: PortalFaqContent;
+  onChange: (next: PortalFaqContent) => void;
+  /** Reseed counter — see the `key` on the editor below. */
+  seed: number;
+}
+
+/**
+ * The FAQ is two levels deep, so the rail shows each group as a heading with
+ * its questions beneath — the same outline a customer sees on the page. Picking
+ * a question opens it; picking the group's own row renames or removes it.
+ */
+export function FaqWorkspace({
+  value,
+  onChange,
+  seed,
+}: FaqWorkspaceProps) {
+  const groups = value.groups ?? [];
+
+  const [selectedId, setSelectedId] = useState<string | null>(
+    groups[0]?.items[0]?.id ?? groups[0]?.id ?? null,
+  );
+
+  const setGroups = (next: PortalFaqGroup[]) =>
+    onChange({ ...value, groups: next });
+
+  // Every selectable row, in display order: the group's own row, then its
+  // questions. Flattening once keeps selection and reordering simple.
+  const rows: RailItem[] = groups.flatMap((group) => [
+    { id: group.id, label: group.title || "Untitled group", heading: "Group" },
+    ...group.items.map((item) => ({
+      id: item.id,
+      label: item.question,
+      indented: true,
+    })),
+  ]);
+
+  useEffect(() => {
+    if (!rows.some((row) => row.id === selectedId)) {
+      setSelectedId(rows[0]?.id ?? null);
+    }
+  }, [rows, selectedId]);
+
+  const groupIndex = groups.findIndex((group) => group.id === selectedId);
+  const selectedGroup = groupIndex >= 0 ? groups[groupIndex] : null;
+
+  const ownerIndex = groups.findIndex((group) =>
+    group.items.some((item) => item.id === selectedId),
+  );
+  const owner = ownerIndex >= 0 ? groups[ownerIndex] : null;
+  const itemIndex =
+    owner?.items.findIndex((item) => item.id === selectedId) ?? -1;
+  const selectedItem = owner && itemIndex >= 0 ? owner.items[itemIndex] : null;
+
+  const move = (id: string, delta: number) => {
+    const asGroup = groups.findIndex((group) => group.id === id);
+    if (asGroup >= 0) {
+      setGroups(moveAt(groups, asGroup, delta));
+      return;
+    }
+
+    const at = groups.findIndex((group) =>
+      group.items.some((item) => item.id === id),
+    );
+    if (at < 0) return;
+    const within = groups[at].items.findIndex((item) => item.id === id);
+    setGroups(
+      replaceAt(groups, at, {
+        ...groups[at],
+        items: moveAt(groups[at].items, within, delta),
+      }),
+    );
+  };
+
+  const canMove = (id: string, delta: number) => {
+    const asGroup = groups.findIndex((group) => group.id === id);
+    if (asGroup >= 0) {
+      const target = asGroup + delta;
+      return target >= 0 && target < groups.length;
+    }
+
+    const at = groups.findIndex((group) =>
+      group.items.some((item) => item.id === id),
+    );
+    if (at < 0) return false;
+    const within = groups[at].items.findIndex((item) => item.id === id);
+    const target = within + delta;
+    return target >= 0 && target < groups[at].items.length;
+  };
+
+  const addQuestion = () => {
+    // Add into the group the author is currently in, or the last one.
+    const target = owner ?? selectedGroup ?? groups[groups.length - 1];
+    if (!target) return;
+
+    const at = groups.findIndex((group) => group.id === target.id);
+    const question = { id: newId(), question: "", answer: "" };
+    setGroups(
+      replaceAt(groups, at, {
+        ...target,
+        items: [...target.items, question],
+      }),
+    );
+    setSelectedId(question.id);
+  };
+
+  const addGroup = () => {
+    const group = { id: newId(), title: "New group", items: [] };
+    setGroups([...groups, group]);
+    setSelectedId(group.id);
+  };
+
+  return (
+    <Group align="flex-start" gap="lg" wrap="nowrap">
+      <Stack gap="xs" style={{ flexShrink: 0 }}>
+        <DocumentRail
+          items={rows}
+          selectedId={selectedId}
+          onSelect={setSelectedId}
+          onMove={move}
+          canMove={canMove}
+          addLabel="Add a question"
+          onAdd={addQuestion}
+          emptyLabel="No groups yet — add one to start."
+        />
+        <Button
+          variant="subtle"
+          size="sm"
+          leftSection={<Plus size={16} />}
+          onClick={addGroup}
+        >
+          Add a group
+        </Button>
+      </Stack>
+
+      {selectedItem && owner ? (
+        <EditorPane
+          title={selectedItem.question}
+          titlePlaceholder="What is the customer asking?"
+          onTitleChange={(question) =>
+            setGroups(
+              replaceAt(groups, ownerIndex, {
+                ...owner,
+                items: replaceAt(owner.items, itemIndex, {
+                  ...selectedItem,
+                  question,
+                }),
+              }),
+            )
+          }
+          onRemove={() =>
+            setGroups(
+              replaceAt(groups, ownerIndex, {
+                ...owner,
+                items: removeAt(owner.items, itemIndex),
+              }),
+            )
+          }
+          removeLabel="Delete this question"
+        >
+          <MarkdownEditor
+            // MDXEditor reads `markdown` only on mount — without a key,
+            // switching questions kept the previous answer on screen.
+            key={`${seed}:${selectedItem.id}`}
+            value={selectedItem.answer}
+            onChange={(answer) =>
+              setGroups(
+                replaceAt(groups, ownerIndex, {
+                  ...owner,
+                  items: replaceAt(owner.items, itemIndex, {
+                    ...selectedItem,
+                    answer,
+                  }),
+                }),
+              )
+            }
+          />
+        </EditorPane>
+      ) : selectedGroup ? (
+        <EditorPane
+          title={selectedGroup.title}
+          titlePlaceholder="Group name"
+          onTitleChange={(title) =>
+            setGroups(replaceAt(groups, groupIndex, { ...selectedGroup, title }))
+          }
+          onRemove={() => setGroups(removeAt(groups, groupIndex))}
+          removeLabel="Delete this group and its questions"
+        >
+          <Stack gap="sm">
+            <Text size="sm" c="dimmed">
+              A group is just a heading on the FAQ page. It holds{" "}
+              {selectedGroup.items.length} question
+              {selectedGroup.items.length === 1 ? "" : "s"} — pick one on the
+              left to edit it.
+            </Text>
+            <TextInput
+              label="Group name"
+              value={selectedGroup.title}
+              onChange={(e) =>
+                setGroups(
+                  replaceAt(groups, groupIndex, {
+                    ...selectedGroup,
+                    title: e.currentTarget.value,
+                  }),
+                )
+              }
+            />
+          </Stack>
+        </EditorPane>
+      ) : (
+        <EmptyPane message="Add a group to get started." />
+      )}
+    </Group>
+  );
+}
+
+export default FaqWorkspace;
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/HelpEditor.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/HelpEditor.tsx
deleted file mode 100644
index e7b648b43..000000000
--- a/apps/edr-freight-web/backoffice/src/pages/portal_content/HelpEditor.tsx
+++ /dev/null
@@ -1,125 +0,0 @@
-import type { PortalHelpContent, PortalHelpSection } from "@edr/types";
-import { Accordion, Button, Card, Divider, Stack, TextInput } from "@mantine/core";
-import { Plus } from "lucide-react";
-
-import { AccordionRow, excerpt } from "./AccordionRow";
-import { moveAt, newId, removeAt, replaceAt } from "./array-helpers";
-import { MarkdownEditor, MarkdownHint } from "./MarkdownEditor";
-import { MediaManager } from "./MediaManager";
-
-interface HelpEditorProps {
-  value: PortalHelpContent;
-  onChange: (next: PortalHelpContent) => void;
-}
-
-/**
- * The help page is built, not filled in: an ordered list of sections, each a
- * heading plus free markdown plus any images or videos. Nothing about the page
- * is fixed except its title, so support can add, reorder or drop a section
- * without a code change.
- */
-export function HelpEditor({ value, onChange }: HelpEditorProps) {
-  // A row written before the free-form conversion has no `sections` at all.
-  // Tolerate it rather than crashing the tab: the migration rewrites it, but
-  // an environment can be mid-deploy.
-  const sections = value.sections ?? [];
-
-  const setSections = (next: PortalHelpSection[]) =>
-    onChange({ ...value, sections: next });
-
-  return (
-    <Stack gap="lg">
-      <Card withBorder padding="md" radius="md">
-        <Stack gap="md">
-          <TextInput
-            label="Page title"
-            value={value.title}
-            onChange={(e) =>
-              onChange({ ...value, title: e.currentTarget.value })
-            }
-          />
-          <TextInput
-            label="Subtitle"
-            value={value.subtitle}
-            onChange={(e) =>
-              onChange({ ...value, subtitle: e.currentTarget.value })
-            }
-          />
-        </Stack>
-      </Card>
-
-      <MarkdownHint />
-
-      <Accordion variant="separated" radius="md" chevronPosition="left">
-        {sections.map((section, index) => (
-          <AccordionRow
-            key={section.id}
-            value={section.id}
-            title={section.heading}
-            subtitle={
-              section.media.length
-                ? `${excerpt(section.body, 60)} · ${section.media.length} attachment${section.media.length === 1 ? "" : "s"}`
-                : excerpt(section.body)
-            }
-            index={index}
-            length={sections.length}
-            onMove={(delta) => setSections(moveAt(sections, index, delta))}
-            onRemove={() => setSections(removeAt(sections, index))}
-          >
-            <Stack gap="md">
-              <TextInput
-                label="Heading"
-                value={section.heading}
-                onChange={(e) =>
-                  setSections(
-                    replaceAt(sections, index, {
-                      ...section,
-                      heading: e.currentTarget.value,
-                    }),
-                  )
-                }
-              />
-
-              <MarkdownEditor
-                label="Body"
-                value={section.body}
-                onChange={(body) =>
-                  setSections(
-                    replaceAt(sections, index, { ...section, body }),
-                  )
-                }
-              />
-
-              <Divider />
-
-              <MediaManager
-                value={section.media}
-                onChange={(media) =>
-                  setSections(
-                    replaceAt(sections, index, { ...section, media }),
-                  )
-                }
-              />
-            </Stack>
-          </AccordionRow>
-        ))}
-      </Accordion>
-
-      <Button
-        variant="light"
-        leftSection={<Plus size={16} />}
-        style={{ alignSelf: "flex-start" }}
-        onClick={() =>
-          setSections([
-            ...sections,
-            { id: newId(), heading: "New section", body: "", media: [] },
-          ])
-        }
-      >
-        Add section
-      </Button>
-    </Stack>
-  );
-}
-
-export default HelpEditor;
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/LegalDocEditor.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/LegalDocEditor.tsx
deleted file mode 100644
index b24bf9be4..000000000
--- a/apps/edr-freight-web/backoffice/src/pages/portal_content/LegalDocEditor.tsx
+++ /dev/null
@@ -1,110 +0,0 @@
-import type { PortalLegalContent } from "@edr/types";
-import { Accordion, Button, Card, Group, Stack, TextInput } from "@mantine/core";
-import { Plus } from "lucide-react";
-
-import { AccordionRow, excerpt } from "./AccordionRow";
-import { moveAt, newId, removeAt, replaceAt } from "./array-helpers";
-import { MarkdownEditor, MarkdownHint } from "./MarkdownEditor";
-
-interface LegalDocEditorProps {
-  value: PortalLegalContent;
-  onChange: (next: PortalLegalContent) => void;
-}
-
-/** Shared by the Privacy and Terms tabs — the two documents have one shape. */
-export function LegalDocEditor({ value, onChange }: LegalDocEditorProps) {
-  const setSections = (sections: PortalLegalContent["sections"]) =>
-    onChange({ ...value, sections });
-
-  return (
-    <Stack gap="lg">
-      <Card withBorder padding="md" radius="md">
-        <Stack gap="md">
-          <Group grow align="flex-start">
-            <TextInput
-              label="Page title"
-              value={value.title}
-              onChange={(e) =>
-                onChange({ ...value, title: e.currentTarget.value })
-              }
-            />
-            <TextInput
-              label="Last updated"
-              description="Free text, e.g. 6 August 2026"
-              value={value.lastUpdated}
-              onChange={(e) =>
-                onChange({ ...value, lastUpdated: e.currentTarget.value })
-              }
-            />
-          </Group>
-
-          <TextInput
-            label="Subtitle"
-            value={value.subtitle}
-            onChange={(e) =>
-              onChange({ ...value, subtitle: e.currentTarget.value })
-            }
-          />
-        </Stack>
-      </Card>
-
-      <MarkdownHint />
-
-      <Accordion variant="separated" radius="md" chevronPosition="left">
-        {value.sections.map((section, index) => (
-          <AccordionRow
-            key={section.id}
-            value={section.id}
-            title={section.heading}
-            subtitle={excerpt(section.body)}
-            index={index}
-            length={value.sections.length}
-            onMove={(delta) => setSections(moveAt(value.sections, index, delta))}
-            onRemove={() => setSections(removeAt(value.sections, index))}
-          >
-            <Stack gap="md">
-              <TextInput
-                label="Heading"
-                value={section.heading}
-                onChange={(e) =>
-                  setSections(
-                    replaceAt(value.sections, index, {
-                      ...section,
-                      heading: e.currentTarget.value,
-                    }),
-                  )
-                }
-              />
-
-              <MarkdownEditor
-                label="Body"
-                value={section.body}
-                onChange={(body) =>
-                  setSections(
-                    replaceAt(value.sections, index, { ...section, body }),
-                  )
-                }
-              />
-            </Stack>
-          </AccordionRow>
-        ))}
-      </Accordion>
-
-      <Button
-        variant="light"
-        leftSection={<Plus size={16} />}
-        style={{ alignSelf: "flex-start" }}
-        onClick={() =>
-          setSections([
-            ...value.sections,
-            { id: newId(), heading: "New section", body: "" },
-          ])
-        }
-      >
-        Add section
-      </Button>
-    </Stack>
-  );
-}
-
-export default LegalDocEditor;
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/Markdown.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/Markdown.tsx
index 53a6937e8..3a70754a5 100644
--- a/apps/edr-freight-web/backoffice/src/pages/portal_content/Markdown.tsx
+++ b/apps/edr-freight-web/backoffice/src/pages/portal_content/Markdown.tsx
@@ -1,22 +1,101 @@
-import ReactMarkdown from "react-markdown";
+import { isPortalVideoSrc, PORTAL_MEDIA_URI_SCHEME } from "@edr/types";
+import { Text } from "@mantine/core";
+import { useEffect, useState } from "react";
+import ReactMarkdown, { defaultUrlTransform } from "react-markdown";
 
+import { resolvePreview } from "./MarkdownEditor";
 // Same preflight fix the editor needs — Mantine's `Typography` defines its list
 // and margin rules with `:where()`, which Tailwind's preflight outranks, so
 // bullets rendered without markers here too.
 import "./markdown-editor.css";
 
 /**
- * Read-only markdown rendering for the version-history preview. Editing goes
- * through `MarkdownEditor` (MDXEditor); this is only for showing what an old
- * version said.
+ * Renders one embedded picture or video. Stored copy holds `minio:<key>`, so
+ * the URL has to be signed before it can be shown; until it resolves the slot
+ * stays empty rather than flashing a broken image.
+ */
+function Embed({ src, alt }: { src: string; alt?: string }) {
+  const [resolved, setResolved] = useState<string | null>(
+    src.startsWith(PORTAL_MEDIA_URI_SCHEME) ? null : src,
+  );
+
+  useEffect(() => {
+    let active = true;
+    void resolvePreview(src).then((url) => {
+      if (active) setResolved(url);
+    });
+    return () => {
+      active = false;
+    };
+  }, [src]);
+
+  if (!resolved) return null;
+
+  // Spans, not <figure>: markdown wraps an image in a paragraph, and a
+  // <figure> inside a <p> is invalid HTML the browser silently re-parents —
+  // which dropped every embed after the first.
+  return (
+    <span style={{ display: "block", margin: "1rem 0" }}>
+      {isPortalVideoSrc(resolved) ? (
+        <video
+          src={resolved}
+          controls
+          preload="metadata"
+          style={{ width: "100%", borderRadius: 8, background: "#000" }}
+        />
+      ) : (
+        <img
+          src={resolved}
+          alt={alt ?? ""}
+          style={{ width: "100%", borderRadius: 8 }}
+        />
+      )}
+      {alt && (
+        <Text component="span" display="block" size="sm" c="dimmed" mt={4}>
+          {alt}
+        </Text>
+      )}
+    </span>
+  );
+}
+
+/**
+ * Read-only markdown rendering, used by the Preview toggle and the version
+ * history. Editing goes through `MarkdownEditor` (MDXEditor).
  *
  * Same options as the portal's renderer — no `rehype-raw`, no custom
  * `urlTransform` — so neither app grows an HTML-injection surface.
  */
+/**
+ * Module scope on purpose. Declared inline, this object is rebuilt on every
+ * render, so React sees a brand-new component type for `img` and remounts
+ * `Embed` each time — which threw away the URL it had just resolved and left
+ * every uploaded picture and video permanently blank.
+ */
+const COMPONENTS = {
+  img: ({ src, alt }: { src?: string; alt?: string }) =>
+    typeof src === "string" ? <Embed src={src} alt={alt} /> : null,
+};
+
+/**
+ * Lets our own `minio:` refs through, and defers everything else to
+ * react-markdown's default vetting (which drops `javascript:` and friends).
+ *
+ * Needed because the default transform allows only http/https/mailto/tel, so
+ * an unresolved `minio:` ref was silently blanked and every uploaded picture
+ * rendered as an empty paragraph. Only the backoffice needs this: the public
+ * bundle has already had these refs replaced with signed https URLs, so the
+ * portal's renderer keeps the stock transform untouched.
+ */
+const urlTransform = (url: string) =>
+  url.startsWith(PORTAL_MEDIA_URI_SCHEME) ? url : defaultUrlTransform(url);
+
 export function Markdown({ children }: { children: string }) {
   return (
     <div className="edr-md-content">
-      <ReactMarkdown>{children}</ReactMarkdown>
+      <ReactMarkdown components={COMPONENTS} urlTransform={urlTransform}>
+        {children}
+      </ReactMarkdown>
     </div>
   );
 }
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/MarkdownEditor.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/MarkdownEditor.tsx
index 83ca7ef46..b053905cf 100644
--- a/apps/edr-freight-web/backoffice/src/pages/portal_content/MarkdownEditor.tsx
+++ b/apps/edr-freight-web/backoffice/src/pages/portal_content/MarkdownEditor.tsx
@@ -1,13 +1,13 @@
 import { PORTAL_MEDIA_URI_SCHEME } from "@edr/types";
-import { Box, Stack, Text } from "@mantine/core";
+import { Box, Button, Group, SegmentedControl, Stack, Text } from "@mantine/core";
 import {
   BlockTypeSelect,
   BoldItalicUnderlineToggles,
   CreateLink,
-  InsertImage,
   InsertThematicBreak,
   ListsToggle,
   MDXEditor,
+  type MDXEditorMethods,
   UndoRedo,
   headingsPlugin,
   imagePlugin,
@@ -19,18 +19,20 @@ import {
   thematicBreakPlugin,
   toolbarPlugin,
 } from "@mdxeditor/editor";
+import { ImagePlus } from "lucide-react";
+import { useRef, useState } from "react";
 import "@mdxeditor/editor/style.css";
 
 import { portalContentService } from "@/services/portal-content.service";
 
+import { Markdown } from "./Markdown";
+import { MediaDialog } from "./MediaDialog";
 // Undoes Tailwind's preflight inside the editor's content area — see the file.
 import "./markdown-editor.css";
 
 interface MarkdownEditorProps {
-  label: string;
   value: string;
   onChange: (next: string) => void;
-  description?: string;
 }
 
 /**
@@ -40,12 +42,12 @@ interface MarkdownEditorProps {
 const previewCache = new Map<string, Promise<string>>();
 
 /**
- * Inserted images are stored as `minio:<key>`, never as the signed URL the
- * upload returns: a presigned URL expires, so persisting one would leave every
- * embedded image broken a few hours later. `imagePreviewHandler` resolves the
- * ref back to a temporary URL purely for display, on both sides of the wire.
+ * Inserted media is stored as `minio:<key>`, never as the signed URL the upload
+ * returns: a presigned URL expires, so persisting one would leave every
+ * embedded picture broken a few hours later. This resolves the ref back to a
+ * temporary URL purely for display.
  */
-function resolvePreview(url: string): Promise<string> {
+export function resolvePreview(url: string): Promise<string> {
   if (!url.startsWith(PORTAL_MEDIA_URI_SCHEME)) return Promise.resolve(url);
 
   const key = url.slice(PORTAL_MEDIA_URI_SCHEME.length);
@@ -59,82 +61,124 @@ function resolvePreview(url: string): Promise<string> {
   return pending;
 }
 
-export function MarkdownEditor({
-  label,
-  value,
-  onChange,
-  description,
-}: MarkdownEditorProps) {
-  return (
-    <Stack gap={6}>
-      <Text size="sm" fw={500}>
-        {label}
-      </Text>
-      {description && (
-        <Text size="xs" c="dimmed">
-          {description}
-        </Text>
-      )}
+export function MarkdownEditor({ value, onChange }: MarkdownEditorProps) {
+  const editorRef = useRef<MDXEditorMethods>(null);
+  const [mediaOpen, setMediaOpen] = useState(false);
+  const [mode, setMode] = useState<"write" | "preview">("write");
 
-      <Box
-        style={{
-          border: "1px solid var(--mantine-color-gray-3)",
-          borderRadius: "var(--mantine-radius-sm)",
-        }}
-      >
-        <MDXEditor
-          markdown={value}
-          contentEditableClassName="edr-md-content"
-          // MDXEditor re-serialises the markdown once on mount, which differs
-          // harmlessly from what was stored (spacing, escaping). Reporting that
-          // as an edit made every tab open "unsaved" and let a Save write a
-          // no-op version, so the normalisation pass is ignored.
-          onChange={(markdown, initialMarkdownNormalize) => {
-            if (!initialMarkdownNormalize) onChange(markdown);
-          }}
-          plugins={[
-            headingsPlugin(),
-            listsPlugin(),
-            quotePlugin(),
-            linkPlugin(),
-            linkDialogPlugin(),
-            thematicBreakPlugin(),
-            imagePlugin({
-              imageUploadHandler: async (file) => {
-                const { key } = await portalContentService.uploadMedia(file);
-                return `${PORTAL_MEDIA_URI_SCHEME}${key}`;
-              },
-              imagePreviewHandler: resolvePreview,
-            }),
-            markdownShortcutPlugin(),
-            toolbarPlugin({
-              toolbarContents: () => (
-                <>
-                  <UndoRedo />
-                  <BoldItalicUnderlineToggles />
-                  <BlockTypeSelect />
-                  <ListsToggle />
-                  <CreateLink />
-                  <InsertImage />
-                  <InsertThematicBreak />
-                </>
-              ),
-            }),
+  return (
+    <Stack gap="sm" style={{ flex: 1, minHeight: 0 }}>
+      <Group justify="space-between" align="center">
+        <Text size="sm" fw={600} c="dimmed">
+          Page text
+        </Text>
+        <SegmentedControl
+          size="xs"
+          value={mode}
+          onChange={(next) => setMode(next as "write" | "preview")}
+          data={[
+            { label: "Write", value: "write" },
+            { label: "Preview", value: "preview" },
           ]}
         />
-      </Box>
+      </Group>
+
+      {mode === "write" ? (
+        <Box
+          style={{
+            border: "1px solid var(--mantine-color-gray-3)",
+            borderRadius: "var(--mantine-radius-md)",
+            background: "#FFFFFF",
+            overflow: "hidden",
+          }}
+        >
+          <MDXEditor
+            ref={editorRef}
+            markdown={value}
+            contentEditableClassName="edr-md-content"
+            // MDXEditor re-serialises the markdown once on mount, which differs
+            // harmlessly from what was stored (spacing, escaping). Reporting
+            // that as an edit made every tab open "unsaved" and let a Save
+            // write a no-op version, so the normalisation pass is ignored.
+            onChange={(markdown, initialMarkdownNormalize) => {
+              if (!initialMarkdownNormalize) onChange(markdown);
+            }}
+            plugins={[
+              headingsPlugin(),
+              listsPlugin(),
+              quotePlugin(),
+              linkPlugin(),
+              linkDialogPlugin(),
+              thematicBreakPlugin(),
+              // Kept for rendering existing images; its own insert button is
+              // replaced by the one below, which also handles video.
+              imagePlugin({ imagePreviewHandler: resolvePreview }),
+              markdownShortcutPlugin(),
+              toolbarPlugin({
+                toolbarContents: () => (
+                  <>
+                    <UndoRedo />
+                    {/* No underline: markdown has none, so MDXEditor emits a
+                        raw <u> tag — and the portal's renderer drops raw HTML
+                        by design, so the author's emphasis would silently
+                        vanish for the customer. */}
+                    <BoldItalicUnderlineToggles options={["Bold", "Italic"]} />
+                    <BlockTypeSelect />
+                    <ListsToggle />
+                    <CreateLink />
+                    <Button
+                      size="compact-sm"
+                      variant="subtle"
+                      leftSection={<ImagePlus size={16} />}
+                      onClick={() => setMediaOpen(true)}
+                    >
+                      Picture or video
+                    </Button>
+                    <InsertThematicBreak />
+                  </>
+                ),
+              }),
+            ]}
+          />
+        </Box>
+      ) : (
+        <Box
+          p="lg"
+          style={{
+            border: "1px solid var(--mantine-color-gray-3)",
+            borderRadius: "var(--mantine-radius-md)",
+            background: "#FFFFFF",
+            minHeight: 240,
+          }}
+        >
+          {/* The same renderer the customer gets — the only place an author can
+              watch an embedded video actually play before publishing. */}
+          <Markdown>{value || "_This page is empty._"}</Markdown>
+        </Box>
+      )}
+
+      <MediaDialog
+        opened={mediaOpen}
+        onClose={() => setMediaOpen(false)}
+        onInsert={(markdown) => {
+          editorRef.current?.insertMarkdown(`\n\n${markdown}\n\n`);
+          // Inserting through the ref bypasses onChange, so push it ourselves.
+          const next = editorRef.current?.getMarkdown();
+          if (next !== undefined) onChange(next);
+        }}
+      />
     </Stack>
   );
 }
 
-/** Reminder of the substitution tokens, rendered once per tab. */
+/** Reminder of the substitution tokens, shown once per document. */
 export function MarkdownHint() {
   return (
     <Text size="xs" c="dimmed">
-      Placeholders resolve from the Contact tab, so one edit there updates every
-      page: <code>{"{{supportEmail}}"}</code> · <code>{"{{supportPhone}}"}</code>{" "}
-      · <code>{"{{supportOffice}}"}</code> · <code>{"{{supportHours}}"}</code> ·{" "}
-      <code>{"{{supportPhoneTel}}"}</code> (inside a tel: link).
+      Type <code>{"{{supportEmail}}"}</code>, <code>{"{{supportPhone}}"}</code>,{" "}
+      <code>{"{{supportOffice}}"}</code> or <code>{"{{supportHours}}"}</code>{" "}
+      anywhere and it fills in from the Contact tab — change it once there and
+      every page updates.
     </Text>
   );
 }
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/MediaDialog.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/MediaDialog.tsx
new file mode 100644
index 000000000..eae3c6f52
--- /dev/null
+++ b/apps/edr-freight-web/backoffice/src/pages/portal_content/MediaDialog.tsx
@@ -0,0 +1,230 @@
+import { PORTAL_MEDIA_URI_SCHEME, SUPPORT_MEDIA_MAX_BYTES } from "@edr/types";
+import {
+  Box,
+  Button,
+  Group,
+  Loader,
+  Modal,
+  Progress,
+  Stack,
+  Text,
+  TextInput,
+} from "@mantine/core";
+import { Film, Image as ImageIcon, UploadCloud } from "lucide-react";
+import { useRef, useState } from "react";
+import toast from "react-hot-toast";
+
+import { portalContentService } from "@/services/portal-content.service";
+
+interface MediaDialogProps {
+  opened: boolean;
+  onClose: () => void;
+  /** Receives the markdown to drop at the cursor. */
+  onInsert: (markdown: string) => void;
+}
+
+const MAX_MB = Math.round(SUPPORT_MEDIA_MAX_BYTES / (1024 * 1024));
+
+/**
+ * Adds a picture or video to the text — drop a file, or browse for one.
+ *
+ * Replaces MDXEditor's built-in image dialog, which asks for a URL, only takes
+ * images, and leaves an author who just wants to show a screenshot with nothing
+ * to do. There is deliberately no "paste a link" field: everything lives in the
+ * platform, so nothing an editor inserts can rot because someone else's server
+ * moved a file.
+ *
+ * Uploads return an object key; the markdown stores `minio:<key>` and the API
+ * signs it fresh on every read.
+ */
+export function MediaDialog({ opened, onClose, onInsert }: MediaDialogProps) {
+  const inputRef = useRef<HTMLInputElement>(null);
+  const [uploading, setUploading] = useState(false);
+  const [progress, setProgress] = useState<number | null>(null);
+  const [dragging, setDragging] = useState(false);
+  const [uploaded, setUploaded] = useState<{
+    key: string;
+    kind: "image" | "video";
+    url: string;
+  } | null>(null);
+  const [caption, setCaption] = useState("");
+
+  const reset = () => {
+    setUploaded(null);
+    setCaption("");
+    setDragging(false);
+    if (inputRef.current) inputRef.current.value = "";
+  };
+
+  const close = () => {
+    reset();
+    onClose();
+  };
+
+  const upload = async (file: File) => {
+    if (file.size > SUPPORT_MEDIA_MAX_BYTES) {
+      toast.error(`That file is over ${MAX_MB} MB.`);
+      return;
+    }
+
+    setUploading(true);
+    setProgress(0);
+    try {
+      setUploaded(await portalContentService.uploadMedia(file, setProgress));
+    } catch (error) {
+      const err = error as {
+        code?: string;
+        response?: { data?: { message?: string } };
+      };
+      const message =
+        err.code === "ECONNABORTED"
+          ? "That upload timed out. Check your connection and try again."
+          : (err.response?.data?.message ?? "Upload failed");
+      toast.error(Array.isArray(message) ? message.join(", ") : message);
+    } finally {
+      setUploading(false);
+      setProgress(null);
+      if (inputRef.current) inputRef.current.value = "";
+    }
+  };
+
+  const insert = () => {
+    if (!uploaded) return;
+    // The caption doubles as alt text, so it is worth prompting for.
+    onInsert(`![${caption}](${PORTAL_MEDIA_URI_SCHEME}${uploaded.key})`);
+    close();
+  };
+
+  return (
+    <Modal
+      opened={opened}
+      onClose={close}
+      title="Add a picture or video"
+      size="lg"
+      centered
+    >
+      <Stack gap="md">
+        {!uploaded ? (
+          <Box
+            onDragOver={(e) => {
+              e.preventDefault();
+              setDragging(true);
+            }}
+            onDragLeave={() => setDragging(false)}
+            onDrop={(e) => {
+              e.preventDefault();
+              setDragging(false);
+              const file = e.dataTransfer.files?.[0];
+              if (file) void upload(file);
+            }}
+            onClick={() => inputRef.current?.click()}
+            style={{
+              border: `2px dashed var(--mantine-color-${dragging ? "green" : "gray"}-4)`,
+              background: dragging
+                ? "var(--mantine-color-green-0)"
+                : "var(--mantine-color-gray-0)",
+              borderRadius: "var(--mantine-radius-md)",
+              padding: "2.5rem 1.5rem",
+              textAlign: "center",
+              cursor: "pointer",
+              transition: "background 120ms, border-color 120ms",
+            }}
+          >
+            {uploading ? (
+              <Stack align="center" gap="xs">
+                <Loader size="sm" />
+                <Text size="sm" c="dimmed">
+                  {progress === null
+                    ? "Uploading…"
+                    : `Uploading… ${progress}%`}
+                </Text>
+                {progress !== null && (
+                  <Progress value={progress} w="60%" size="sm" />
+                )}
+              </Stack>
+            ) : (
+              <Stack align="center" gap="xs">
+                <UploadCloud size={32} strokeWidth={1.5} />
+                <Text fw={500}>Drop a file here, or click to browse</Text>
+                <Text size="sm" c="dimmed">
+                  Pictures (PNG, JPG, GIF) and videos (MP4, WebM) up to {MAX_MB} MB
+                </Text>
+              </Stack>
+            )}
+          </Box>
+        ) : (
+          <Stack gap="md">
+            <Box
+              style={{
+                border: "1px solid var(--mantine-color-gray-3)",
+                borderRadius: "var(--mantine-radius-md)",
+                padding: "0.75rem",
+                background: "var(--mantine-color-gray-0)",
+              }}
+            >
+              {uploaded.kind === "video" ? (
+                <video
+                  src={uploaded.url}
+                  controls
+                  style={{ width: "100%", maxHeight: 320, borderRadius: 8 }}
+                />
+              ) : (
+                <img
+                  src={uploaded.url}
+                  alt=""
+                  style={{
+                    width: "100%",
+                    maxHeight: 320,
+                    objectFit: "contain",
+                    borderRadius: 8,
+                  }}
+                />
+              )}
+            </Box>
+
+            <Group gap="xs" c="dimmed">
+              {uploaded.kind === "video" ? (
+                <Film size={16} />
+              ) : (
+                <ImageIcon size={16} />
+              )}
+              <Text size="sm">
+                {uploaded.kind === "video" ? "Video" : "Picture"} uploaded
+              </Text>
+            </Group>
+
+            <TextInput
+              label="Caption"
+              description="Shown under the picture, and read aloud by screen readers. Optional."
+              value={caption}
+              onChange={(e) => setCaption(e.currentTarget.value)}
+              autoFocus
+            />
+          </Stack>
+        )}
+
+        <input
+          ref={inputRef}
+          type="file"
+          accept="image/*,video/*"
+          hidden
+          onChange={(e) => {
+            const file = e.currentTarget.files?.[0];
+            if (file) void upload(file);
+          }}
+        />
+
+        <Group justify="space-between">
+          <Button variant="subtle" onClick={uploaded ? reset : close}>
+            {uploaded ? "Choose a different file" : "Cancel"}
+          </Button>
+          <Button onClick={insert} disabled={!uploaded}>
+            Add to the page
+          </Button>
+        </Group>
+      </Stack>
+    </Modal>
+  );
+}
+
+export default MediaDialog;
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/MediaManager.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/MediaManager.tsx
deleted file mode 100644
index a80bd3b55..000000000
--- a/apps/edr-freight-web/backoffice/src/pages/portal_content/MediaManager.tsx
+++ /dev/null
@@ -1,122 +0,0 @@
-import type { PortalMedia } from "@edr/types";
-import {
-  ActionIcon,
-  Button,
-  Group,
-  Paper,
-  Stack,
-  Text,
-  TextInput,
-  Tooltip,
-} from "@mantine/core";
-import { Film, Image as ImageIcon, Trash2, Upload } from "lucide-react";
-import { useRef, useState } from "react";
-import toast from "react-hot-toast";
-
-import { portalContentService } from "@/services/portal-content.service";
-
-import { newId, removeAt, replaceAt } from "./array-helpers";
-
-interface MediaManagerProps {
-  value: PortalMedia[];
-  onChange: (next: PortalMedia[]) => void;
-}
-
-/**
- * Attachments for one help section. Uploads store the MinIO object *key*; the
- * signed URL the upload returns is short-lived and is never persisted, so the
- * list shows the key rather than pretending to be a gallery.
- */
-export function MediaManager({ value, onChange }: MediaManagerProps) {
-  const inputRef = useRef<HTMLInputElement>(null);
-  const [uploading, setUploading] = useState(false);
-
-  const upload = async (file: File) => {
-    setUploading(true);
-    try {
-      const { key, kind } = await portalContentService.uploadMedia(file);
-      onChange([...value, { id: newId(), kind, src: key, caption: null }]);
-    } catch (error) {
-      const message =
-        (error as { response?: { data?: { message?: string } } })?.response?.data
-          ?.message ?? "Upload failed";
-      toast.error(Array.isArray(message) ? message.join(", ") : message);
-    } finally {
-      setUploading(false);
-      if (inputRef.current) inputRef.current.value = "";
-    }
-  };
-
-  return (
-    <Stack gap="xs">
-      <Text size="sm" fw={500}>
-        Attachments
-      </Text>
-
-      {value.map((item, index) => (
-        <Paper key={item.id} withBorder p="xs" radius="sm">
-          <Group wrap="nowrap" align="center" gap="sm">
-            {item.kind === "video" ? (
-              <Film size={18} />
-            ) : (
-              <ImageIcon size={18} />
-            )}
-
-            <Stack gap={2} style={{ flex: 1, minWidth: 0 }}>
-              <Text size="xs" c="dimmed" truncate>
-                {item.src}
-              </Text>
-              <TextInput
-                size="xs"
-                placeholder="Caption (optional)"
-                value={item.caption ?? ""}
-                onChange={(e) =>
-                  onChange(
-                    replaceAt(value, index, {
-                      ...item,
-                      caption: e.currentTarget.value || null,
-                    }),
-                  )
-                }
-              />
-            </Stack>
-
-            <Tooltip label="Remove attachment">
-              <ActionIcon
-                variant="subtle"
-                color="red"
-                onClick={() => onChange(removeAt(value, index))}
-              >
-                <Trash2 size={16} />
-              </ActionIcon>
-            </Tooltip>
-          </Group>
-        </Paper>
-      ))}
-
-      <input
-        ref={inputRef}
-        type="file"
-        accept="image/*,video/*"
-        hidden
-        onChange={(e) => {
-          const file = e.currentTarget.files?.[0];
-          if (file) void upload(file);
-        }}
-      />
-
-      <Button
-        variant="light"
-        size="xs"
-        loading={uploading}
-        leftSection={<Upload size={14} />}
-        style={{ alignSelf: "flex-start" }}
-        onClick={() => inputRef.current?.click()}
-      >
-        Upload image or video
-      </Button>
-    </Stack>
-  );
-}
-
-export default MediaManager;
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/PortalContentPage.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/PortalContentPage.tsx
index 17d5d190f..4fc51174d 100644
--- a/apps/edr-freight-web/backoffice/src/pages/portal_content/PortalContentPage.tsx
+++ b/apps/edr-freight-web/backoffice/src/pages/portal_content/PortalContentPage.tsx
@@ -26,9 +26,9 @@ import {
   useUpdatePortalDoc,
 } from "@/hooks/portal-content/usePortalContentAdmin";
 
-import { FaqEditor } from "./FaqEditor";
-import { HelpEditor } from "./HelpEditor";
-import { LegalDocEditor } from "./LegalDocEditor";
+import { FaqWorkspace } from "./FaqWorkspace";
+import { MarkdownHint } from "./MarkdownEditor";
+import { SectionWorkspace } from "./SectionWorkspace";
 import { VersionHistoryModal } from "./VersionHistoryModal";
 
 const TABS: { slug: SupportDocSlug; label: string }[] = [
@@ -89,6 +89,14 @@ function DocumentTab({ slug }: { slug: SupportDocSlug }) {
   const [note, setNote] = useState("");
   const [historyOpen, setHistoryOpen] = useState(false);
 
+  /**
+   * Bumped every time the draft is replaced wholesale rather than edited —
+   * initial load, save, restore, Reset. The editors key off it to remount,
+   * because MDXEditor reads its markdown only on mount and would otherwise
+   * keep showing text the draft no longer holds.
+   */
+  const [seed, setSeed] = useState(0);
+
   // Reseed only when the server's version number moves (load, save, restore).
   // Keying off `data` itself would let a background refetch wipe edits that are
   // still in progress.
@@ -98,6 +106,7 @@ function DocumentTab({ slug }: { slug: SupportDocSlug }) {
       seededVersion.current = data.version;
       setDraft(data.payload);
       setNote("");
+      setSeed((n) => n + 1);
     }
   }, [data]);
 
@@ -108,6 +117,7 @@ function DocumentTab({ slug }: { slug: SupportDocSlug }) {
   const reset = () => {
     setDraft(data.payload);
     setNote("");
+    setSeed((n) => n + 1);
   };
 
   return (
@@ -174,7 +184,12 @@ function DocumentTab({ slug }: { slug: SupportDocSlug }) {
         </Group>
       </Card>
 
-      <DocumentEditor slug={slug} value={draft} onChange={setDraft} />
+      <DocumentEditor
+        slug={slug}
+        value={draft}
+        onChange={setDraft}
+        seed={seed}
+      />
 
       <VersionHistoryModal
         slug={slug}
@@ -191,10 +206,13 @@ function DocumentEditor({
   slug,
   value,
   onChange,
+  seed,
 }: {
   slug: SupportDocSlug;
   value: SupportDocPayload;
   onChange: (next: SupportDocPayload) => void;
+  /** Reseed counter; bumping it remounts the editors. */
+  seed: number;
 }) {
   switch (slug) {
     case "CONTACT":
@@ -204,23 +222,98 @@ function DocumentEditor({
           onChange={onChange}
         />
       );
-    case "HELP":
-      return (
-        <HelpEditor value={value as PortalHelpContent} onChange={onChange} />
-      );
     case "FAQ":
-      return <FaqEditor value={value as PortalFaqContent} onChange={onChange} />;
-    case "PRIVACY":
-    case "TERMS":
       return (
-        <LegalDocEditor
-          value={value as PortalLegalContent}
+        <FaqWorkspace
+          value={value as PortalFaqContent}
           onChange={onChange}
+          seed={seed}
         />
       );
+    case "HELP":
+    case "PRIVACY":
+    case "TERMS": {
+      // All three are a title, a subtitle and a list of pages, so they share
+      // one workspace. `sections` is guarded because a row written before the
+      // free-form conversion has none.
+      const doc = value as PortalHelpContent | PortalLegalContent;
+      return (
+        <DocumentShell
+          value={doc}
+          onChange={onChange}
+          showLastUpdated={slug !== "HELP"}
+          seed={seed}
+        />
+      );
+    }
   }
 }
 
+/**
+ * Title, subtitle and (for the legal documents) the "last updated" line, above
+ * the page list. These three fields describe the whole document, so they sit
+ * apart from the page being edited.
+ */
+function DocumentShell({
+  value,
+  onChange,
+  showLastUpdated,
+  seed,
+}: {
+  value: PortalHelpContent | PortalLegalContent;
+  onChange: (next: SupportDocPayload) => void;
+  showLastUpdated: boolean;
+  seed: number;
+}) {
+  const legal = value as PortalLegalContent;
+
+  return (
+    <Stack gap="lg">
+      <Card withBorder padding="lg" radius="lg" bg="#FFFFFF">
+        <Stack gap="md">
+          <Group grow align="flex-start">
+            <TextInput
+              label="Page title"
+              description="The big heading customers see"
+              value={value.title}
+              onChange={(e) =>
+                onChange({ ...value, title: e.currentTarget.value })
+              }
+            />
+            {showLastUpdated && (
+              <TextInput
+                label="Last updated"
+                description="Free text, e.g. 6 August 2026"
+                value={legal.lastUpdated}
+                onChange={(e) =>
+                  onChange({ ...legal, lastUpdated: e.currentTarget.value })
+                }
+              />
+            )}
+          </Group>
+
+          <TextInput
+            label="Intro line"
+            description="One sentence under the heading"
+            value={value.subtitle}
+            onChange={(e) =>
+              onChange({ ...value, subtitle: e.currentTarget.value })
+            }
+          />
+
+          <MarkdownHint />
+        </Stack>
+      </Card>
+
+      <SectionWorkspace
+        sections={value.sections ?? []}
+        onChange={(sections) => onChange({ ...value, sections })}
+        seed={seed}
+      />
+    </Stack>
+  );
+}
+
 /**
  * Four fields, so no separate file. These values feed the help page's contact
  * cards and resolve the `{{supportEmail}}`-style placeholders used throughout
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/SectionWorkspace.tsx b/apps/edr-freight-web/backoffice/src/pages/portal_content/SectionWorkspace.tsx
new file mode 100644
index 000000000..b59e12660
--- /dev/null
+++ b/apps/edr-freight-web/backoffice/src/pages/portal_content/SectionWorkspace.tsx
@@ -0,0 +1,107 @@
+import type { PortalDocSection } from "@edr/types";
+import { Group, Stack } from "@mantine/core";
+import { useEffect, useState } from "react";
+
+import { moveAt, newId, removeAt, replaceAt } from "./array-helpers";
+import { DocumentRail } from "./DocumentRail";
+import { EditorPane, EmptyPane } from "./EditorPane";
+import { MarkdownEditor } from "./MarkdownEditor";
+
+interface SectionWorkspaceProps {
+  sections: PortalDocSection[];
+  onChange: (next: PortalDocSection[]) => void;
+  /** Reseed counter — see the `key` on the editor below. */
+  seed: number;
+}
+
+/**
+ * Page-at-a-time editing for any document that is a list of sections — the help
+ * page and both legal documents. The list on the left is the document's table
+ * of contents; the pane on the right is the page you are working on.
+ */
+export function SectionWorkspace({
+  sections,
+  onChange,
+  seed,
+}: SectionWorkspaceProps) {
+  const [selectedId, setSelectedId] = useState<string | null>(
+    sections[0]?.id ?? null,
+  );
+
+  // Keep a valid selection when the open page is deleted, or when the tab is
+  // reseeded after a save or a restore.
+  useEffect(() => {
+    if (!sections.some((section) => section.id === selectedId)) {
+      setSelectedId(sections[0]?.id ?? null);
+    }
+  }, [sections, selectedId]);
+
+  const index = sections.findIndex((section) => section.id === selectedId);
+  const selected = index >= 0 ? sections[index] : null;
+
+  const addSection = () => {
+    const section = { id: newId(), heading: "", body: "" };
+    onChange([...sections, section]);
+    setSelectedId(section.id);
+  };
+
+  return (
+    <Group align="flex-start" gap="lg" wrap="nowrap">
+      <DocumentRail
+        items={sections.map((section) => ({
+          id: section.id,
+          label: section.heading,
+        }))}
+        selectedId={selectedId}
+        onSelect={setSelectedId}
+        onMove={(id, delta) =>
+          onChange(
+            moveAt(
+              sections,
+              sections.findIndex((section) => section.id === id),
+              delta,
+            ),
+          )
+        }
+        canMove={(id, delta) => {
+          const at = sections.findIndex((section) => section.id === id);
+          const target = at + delta;
+          return target >= 0 && target < sections.length;
+        }}
+        addLabel="Add a page"
+        onAdd={addSection}
+        emptyLabel="This document has no pages yet."
+      />
+
+      {selected ? (
+        <EditorPane
+          title={selected.heading}
+          titlePlaceholder="Page heading"
+          onTitleChange={(heading) =>
+            onChange(replaceAt(sections, index, { ...selected, heading }))
+          }
+          onRemove={() => onChange(removeAt(sections, index))}
+          removeLabel="Delete this page"
+        >
+          <Stack gap="md">
+            <MarkdownEditor
+              // MDXEditor reads `markdown` only when it mounts, so without a
+              // key it keeps showing the previously-opened page's text. The
+              // counter is in the key too, so save, restore and Reset reseed it
+              // instead of leaving stale content on screen.
+              key={`${seed}:${selected.id}`}
+              value={selected.body}
+              onChange={(body) =>
+                onChange(replaceAt(sections, index, { ...selected, body }))
+              }
+            />
+          </Stack>
+        </EditorPane>
+      ) : (
+        <EmptyPane message="Add a page to get started." />
+      )}
+    </Group>
+  );
+}
+
+export default SectionWorkspace;
diff --git a/apps/edr-freight-web/backoffice/src/pages/portal_content/version-preview.ts b/apps/edr-freight-web/backoffice/src/pages/portal_content/version-preview.ts
index 465c91aba..42e7fb8ab 100644
--- a/apps/edr-freight-web/backoffice/src/pages/portal_content/version-preview.ts
+++ b/apps/edr-freight-web/backoffice/src/pages/portal_content/version-preview.ts
@@ -39,11 +39,11 @@ export function summarizeVersion(
       return [
         { label: "Title", body: help.title },
         { label: "Subtitle", body: help.subtitle },
-        ...help.sections.map((section) => ({
+        // Pictures and videos live in the body, so they render in the preview
+        // alongside the text they belong to — nothing to summarise separately.
+        ...(help.sections ?? []).map((section) => ({
           label: section.heading,
-          body: section.media.length
-            ? `${section.body}\n\n_${section.media.length} attachment${section.media.length === 1 ? "" : "s"}: ${section.media.map((m) => m.src).join(", ")}_`
-            : section.body,
+          body: section.body,
         })),
       ];
     }
diff --git a/apps/edr-freight-web/backoffice/src/services/portal-content.service.ts b/apps/edr-freight-web/backoffice/src/services/portal-content.service.ts
index 0f42b2a5a..a1bbb3260 100644
--- a/apps/edr-freight-web/backoffice/src/services/portal-content.service.ts
+++ b/apps/edr-freight-web/backoffice/src/services/portal-content.service.ts
@@ -64,6 +64,7 @@ export const portalContentService = {
    */
   async uploadMedia(
     file: File,
+    onProgress?: (percent: number | null) => void,
   ): Promise<{ key: string; kind: PortalMediaKind; url: string }> {
     const form = new FormData();
     form.append("file", file);
@@ -72,7 +73,15 @@ export const portalContentService = {
       key: string;
       kind: PortalMediaKind;
       url: string;
-    }>(`${ROOT}/media`, form);
+    }>(`${ROOT}/media`, form, {
+      // A video is big enough that a stalled connection would otherwise sit on
+      // a spinner forever with nothing to tell the author it had failed.
+      timeout: 2 * 60 * 1000,
+      onUploadProgress: (event) =>
+        onProgress?.(
+          event.total ? Math.round((event.loaded / event.total) * 100) : null,
+        ),
+    });
     return data;
   },
 
diff --git a/apps/edr-freight-web/portal/src/pages/support/DocShell.tsx b/apps/edr-freight-web/portal/src/pages/support/DocShell.tsx
index 4808f5d52..b4646e0cc 100644
--- a/apps/edr-freight-web/portal/src/pages/support/DocShell.tsx
+++ b/apps/edr-freight-web/portal/src/pages/support/DocShell.tsx
@@ -20,6 +20,8 @@ interface DocShellProps {
   meta?: string;
   /** Path of the current page, so it is not linked to itself. */
   current: string;
+  /** Contents column, mirroring the page list editors see in the backoffice. */
+  sidebar?: ReactNode;
   children: ReactNode;
 }
 
@@ -33,12 +35,13 @@ export function DocShell({
   subtitle,
   meta,
   current,
+  sidebar,
   children,
 }: DocShellProps) {
   return (
     <div className="min-h-screen bg-background text-foreground">
       <header className="sticky top-0 z-50 border-b border-border bg-background/80 backdrop-blur-xl">
-        <div className="mx-auto flex max-w-4xl items-center justify-between gap-4 px-6 py-4">
+        <div className="mx-auto flex max-w-6xl items-center justify-between gap-4 px-6 py-4">
           <Link to="/" className="flex items-center gap-3">
             <div className="flex size-10 items-center justify-center rounded-2xl bg-primary text-primary-foreground">
               <Train className="size-5" />
@@ -56,7 +59,7 @@ export function DocShell({
         </div>
       </header>
 
-      <main className="mx-auto max-w-4xl px-6 py-12">
+      <main className="mx-auto max-w-6xl px-6 py-12">
         <h1 className="text-4xl font-black tracking-tight">{title}</h1>
         <p className="mt-4 text-lg leading-8 text-muted-foreground">
           {subtitle}
@@ -65,11 +68,18 @@ export function DocShell({
           <p className="mt-2 text-sm text-muted-foreground">{meta}</p>
         )}
 
-        <div className="mt-10">{children}</div>
+        {sidebar ? (
+          <div className="mt-10 flex flex-col gap-8 lg:flex-row lg:gap-10">
+            {sidebar}
+            <div className="min-w-0 flex-1">{children}</div>
+          </div>
+        ) : (
+          <div className="mt-10">{children}</div>
+        )}
       </main>
 
       <footer className="border-t border-border py-8">
-        <div className="mx-auto flex max-w-4xl flex-col items-center justify-between gap-4 px-6 text-sm text-muted-foreground md:flex-row">
+        <div className="mx-auto flex max-w-6xl flex-col items-center justify-between gap-4 px-6 text-sm text-muted-foreground md:flex-row">
           <span>© 2026 EDR Freight. All rights reserved.</span>
           <nav className="flex flex-wrap items-center justify-center gap-x-6 gap-y-2">
             {DOC_LINKS.filter((l) => l.to !== current).map((link) => (
@@ -96,8 +106,11 @@ export function DocShell({
 export function DocSections({ sections }: { sections: PortalDocSection[] }) {
   return (
     <div className="space-y-10">
-      {sections.map((section) => (
-        <section key={section.id}>
+      {/* Guarded: this is API-supplied, and these routes are public. */}
+      {(sections ?? []).map((section) => (
+        // `id` doubles as the anchor the contents list and #deep-links target;
+        // `scroll-mt` keeps the heading clear of the sticky header.
+        <section key={section.id} id={section.id} className="scroll-mt-24">
           <h2 className="text-xl font-bold tracking-tight">
             {section.heading}
           </h2>
diff --git a/apps/edr-freight-web/portal/src/pages/support/DocSidebar.tsx b/apps/edr-freight-web/portal/src/pages/support/DocSidebar.tsx
new file mode 100644
index 000000000..eec27c28b
--- /dev/null
+++ b/apps/edr-freight-web/portal/src/pages/support/DocSidebar.tsx
@@ -0,0 +1,117 @@
+import { useEffect, useState } from "react";
+
+export interface DocNavItem {
+  id: string;
+  label: string;
+}
+
+/**
+ * Highlights whichever section is currently on screen, so a long policy tells
+ * the reader where they are. Watches the top band of the viewport, which is
+ * what makes the highlight change as a heading scrolls past rather than only
+ * when a whole section fits.
+ */
+export function useActiveSection(ids: string[]): string | null {
+  const [active, setActive] = useState<string | null>(ids[0] ?? null);
+
+  useEffect(() => {
+    if (ids.length === 0) return;
+
+    const observer = new IntersectionObserver(
+      (entries) => {
+        const visible = entries
+          .filter((entry) => entry.isIntersecting)
+          .sort((a, b) => a.boundingClientRect.top - b.boundingClientRect.top);
+        if (visible[0]) setActive(visible[0].target.id);
+      },
+      // Top ~quarter of the viewport, below the sticky header.
+      { rootMargin: "-80px 0px -70% 0px", threshold: 0 },
+    );
+
+    for (const id of ids) {
+      const element = document.getElementById(id);
+      if (element) observer.observe(element);
+    }
+    return () => observer.disconnect();
+  }, [ids.join("|")]); // eslint-disable-line react-hooks/exhaustive-deps
+
+  return active;
+}
+
+interface DocSidebarProps {
+  items: DocNavItem[];
+  activeId: string | null;
+  /**
+   * Paged mode (the help page): selecting swaps the visible section. Omit for
+   * table-of-contents mode, where entries are anchors into one long document.
+   */
+  onSelect?: (id: string) => void;
+  heading?: string;
+}
+
+/**
+ * The document's contents, mirroring the page list an editor sees in the
+ * backoffice. Sticky on wide screens; above the content on narrow ones, where
+ * a fixed column would eat the reading width.
+ */
+export function DocSidebar({
+  items,
+  activeId,
+  onSelect,
+  heading = "Contents",
+}: DocSidebarProps) {
+  if (items.length === 0) return null;
+
+  return (
+    <nav
+      aria-label={heading}
+      // Divider: a right edge once the columns sit side by side, a bottom edge
+      // while they are stacked — so the contents always reads as its own
+      // column rather than as text that happens to be to the left.
+      className="border-b border-border pb-6 lg:sticky lg:top-24 lg:w-64 lg:shrink-0 lg:self-start lg:border-b-0 lg:border-r lg:pb-0 lg:pr-6"
+    >
+      <p className="px-3 text-xs font-bold uppercase tracking-wider text-foreground/60">
+        {heading}
+      </p>
+
+      <ul className="mt-3 max-h-[60vh] space-y-1 overflow-y-auto lg:max-h-[calc(100vh-10rem)]">
+        {items.map((item) => {
+          const active = item.id === activeId;
+          // Inactive entries were `muted-foreground`, which is the same tone as
+          // body copy and left the list looking disabled. These are navigation,
+          // so they sit closer to full foreground and darken on hover.
+          const className = `block w-full rounded-xl px-3 py-2 text-left text-sm transition ${
+            active
+              ? "bg-accent font-semibold text-foreground"
+              : "text-foreground/75 hover:bg-accent/60 hover:text-foreground"
+          }`;
+
+          return (
+            <li key={item.id}>
+              {onSelect ? (
+                <button
+                  type="button"
+                  onClick={() => onSelect(item.id)}
+                  aria-current={active ? "page" : undefined}
+                  className={className}
+                >
+                  {item.label}
+                </button>
+              ) : (
+                <a
+                  href={`#${item.id}`}
+                  aria-current={active ? "true" : undefined}
+                  className={className}
+                >
+                  {item.label}
+                </a>
+              )}
+            </li>
+          );
+        })}
+      </ul>
+    </nav>
+  );
+}
+
+export default DocSidebar;
diff --git a/apps/edr-freight-web/portal/src/pages/support/FaqPage.tsx b/apps/edr-freight-web/portal/src/pages/support/FaqPage.tsx
index 7aa702a21..2edf69c9e 100644
--- a/apps/edr-freight-web/portal/src/pages/support/FaqPage.tsx
+++ b/apps/edr-freight-web/portal/src/pages/support/FaqPage.tsx
@@ -4,22 +4,38 @@ import { Link } from "react-router-dom";
 import { usePortalContent } from "@/hooks/usePortalContent";
 
 import { DocShell } from "./DocShell";
+import { DocSidebar, useActiveSection } from "./DocSidebar";
 import { Markdown } from "./Markdown";
 
 export default function FaqPage() {
   // Never undefined — see TermsPage.
   const { data } = usePortalContent();
   const faq = data!.faq;
+  const groups = faq.groups ?? [];
+
+  // Contents lists the groups; individual questions stay as the disclosure
+  // rows below, which is already the fastest way to scan them.
+  const activeId = useActiveSection(groups.map((group) => group.id));
 
   return (
-    <DocShell current="/faq" title={faq.title} subtitle={faq.subtitle}>
+    <DocShell
+      current="/faq"
+      title={faq.title}
+      subtitle={faq.subtitle}
+      sidebar={
+        <DocSidebar
+          items={groups.map((group) => ({ id: group.id, label: group.title }))}
+          activeId={activeId}
+        />
+      }
+    >
       <div className="space-y-10">
-        {faq.groups.map((group) => (
-          <section key={group.id}>
+        {groups.map((group) => (
+          <section key={group.id} id={group.id} className="scroll-mt-24">
             <h2 className="text-xl font-bold tracking-tight">{group.title}</h2>
 
             <div className="mt-4 space-y-3">
-              {group.items.map((item) => (
+              {(group.items ?? []).map((item) => (
                 // Native disclosure: keyboard- and screen-reader-accessible
                 // without any state of our own.
                 <details
diff --git a/apps/edr-freight-web/portal/src/pages/support/HelpPage.tsx b/apps/edr-freight-web/portal/src/pages/support/HelpPage.tsx
index 37c748d79..f55b9145f 100644
--- a/apps/edr-freight-web/portal/src/pages/support/HelpPage.tsx
+++ b/apps/edr-freight-web/portal/src/pages/support/HelpPage.tsx
@@ -1,74 +1,75 @@
-import type { PortalMedia } from "@edr/types";
+import { useEffect, useState } from "react";
+import { useLocation, useNavigate } from "react-router-dom";
 
 import { usePortalContent } from "@/hooks/usePortalContent";
 
 import { DocShell } from "./DocShell";
+import { DocSidebar } from "./DocSidebar";
 import { Markdown } from "./Markdown";
-import { safeMediaSrc } from "./portal-content";
 
 /**
- * An attached image or video. The API has already swapped stored MinIO keys for
- * freshly signed URLs, so `src` is ready to render — `safeMediaSrc` is a last
- * check that an admin-entered value is a path or an https URL.
+ * Help is browsed a page at a time, mirroring how it is written: the sidebar is
+ * the list of pages, and picking one swaps the panel. Unlike the legal
+ * documents nobody reads help end to end — they arrive with one question — so
+ * showing a single answer beats a wall of every topic at once.
  */
-function Media({ item }: { item: PortalMedia }) {
-  const src = safeMediaSrc(item.src);
-  if (!src) return null;
-
-  return (
-    <figure className="mt-6">
-      {item.kind === "video" ? (
-        // preload="metadata" so a large file is not pulled on every visit; the
-        // browser fetches it only once playback starts.
-        <video
-          controls
-          preload="metadata"
-          className="w-full rounded-[32px] border border-border bg-black"
-        >
-          <source src={src} />
-          Your browser cannot play this video.{" "}
-          <a href={src}>Download it instead</a>.
-        </video>
-      ) : (
-        <img
-          src={src}
-          alt={item.caption ?? ""}
-          loading="lazy"
-          className="w-full rounded-[32px] border border-border"
-        />
-      )}
-
-      {item.caption && (
-        <figcaption className="mt-2 text-sm text-muted-foreground">
-          {item.caption}
-        </figcaption>
-      )}
-    </figure>
-  );
-}
-
 export default function HelpPage() {
   // Never undefined — see TermsPage.
   const { data } = usePortalContent();
   const help = data!.help;
+  const sections = help.sections ?? [];
+
+  const navigate = useNavigate();
+  const { hash } = useLocation();
+
+  // The open page lives in the URL, so a link to a specific topic works and
+  // Back steps between topics.
+  const fromHash = hash ? decodeURIComponent(hash.slice(1)) : "";
+  const [selectedId, setSelectedId] = useState(
+    () => fromHash || sections[0]?.id || "",
+  );
+
+  useEffect(() => {
+    const valid = sections.some((section) => section.id === selectedId);
+    if (!valid) setSelectedId(fromHash || sections[0]?.id || "");
+  }, [sections, selectedId, fromHash]);
+
+  useEffect(() => {
+    if (fromHash && fromHash !== selectedId) setSelectedId(fromHash);
+  }, [fromHash]); // eslint-disable-line react-hooks/exhaustive-deps
+
+  const selected =
+    sections.find((section) => section.id === selectedId) ?? sections[0];
 
   return (
-    <DocShell current="/help" title={help.title} subtitle={help.subtitle}>
-      <div className="space-y-12">
-        {help.sections.map((section) => (
-          <section key={section.id}>
-            <h2 className="text-xl font-bold tracking-tight">
-              {section.heading}
-            </h2>
-
-            <Markdown>{section.body}</Markdown>
-
-            {section.media.map((item) => (
-              <Media key={item.id} item={item} />
-            ))}
-          </section>
-        ))}
-      </div>
+    <DocShell
+      current="/help"
+      title={help.title}
+      subtitle={help.subtitle}
+      sidebar={
+        <DocSidebar
+          heading="Topics"
+          items={sections.map((section) => ({
+            id: section.id,
+            label: section.heading,
+          }))}
+          activeId={selected?.id ?? null}
+          onSelect={(id) => {
+            setSelectedId(id);
+            navigate(`#${id}`);
+            window.scrollTo({ top: 0, behavior: "smooth" });
+          }}
+        />
+      }
+    >
+      {selected && (
+        <section>
+          <h2 className="text-2xl font-bold tracking-tight">
+            {selected.heading}
+          </h2>
+          <Markdown>{selected.body}</Markdown>
+        </section>
+      )}
     </DocShell>
   );
 }
diff --git a/apps/edr-freight-web/portal/src/pages/support/Markdown.tsx b/apps/edr-freight-web/portal/src/pages/support/Markdown.tsx
index 11924cf23..646187f6c 100644
--- a/apps/edr-freight-web/portal/src/pages/support/Markdown.tsx
+++ b/apps/edr-freight-web/portal/src/pages/support/Markdown.tsx
@@ -1,5 +1,8 @@
+import { isPortalVideoSrc } from "@edr/types";
 import ReactMarkdown from "react-markdown";
 
+import { safeMediaSrc } from "./portal-content";
+
 /**
  * Renders admin-authored markdown from the support-content API.
  *
@@ -10,7 +13,9 @@ import ReactMarkdown from "react-markdown";
  * Two things must stay absent for that to hold:
  *   - `rehype-raw`, which would start rendering raw HTML embedded in the copy;
  *   - a custom `urlTransform`, which would override the built-in stripping of
- *     `javascript:` and `data:` hrefs.
+ *     `javascript:` and `data:` hrefs. That transform is now the *only* thing
+ *     vetting embedded media URLs, since they are authored inside the markdown
+ *     rather than validated field-by-field on the API.
  *
  * `remark-gfm` is also left out: tables and strikethrough are not used in the
  * legal or FAQ copy, and CommonMark already covers lists, emphasis and links.
@@ -51,17 +56,55 @@ export function Markdown({ children }: { children: string }) {
         h3: ({ children: content }) => (
           <h3 className="mt-6 font-bold tracking-tight">{content}</h3>
         ),
-        // Images embedded by the editor. The API has already resolved these to
-        // signed URLs; react-markdown's default urlTransform still guards the
-        // scheme.
-        img: ({ src, alt }) => (
-          <img
-            src={typeof src === "string" ? src : undefined}
-            alt={alt ?? ""}
-            loading="lazy"
-            className="mt-4 w-full rounded-2xl border border-border"
-          />
-        ),
+        /**
+         * Images *and* videos: both are written with markdown's image syntax,
+         * and the element is chosen from the file extension. `src` here has
+         * already been through react-markdown's url transform; `safeMediaSrc`
+         * narrows it further to same-origin paths and https.
+         */
+        img: ({ src, alt }) => {
+          const resolved =
+            typeof src === "string" ? safeMediaSrc(src) : null;
+          if (!resolved) return null;
+
+          // Spans, not <figure>/<figcaption>: markdown wraps an image in a
+          // paragraph, and a <figure> inside a <p> is invalid HTML that the
+          // browser silently re-parents, which drops sibling content.
+          const caption = alt ? (
+            <span className="mt-2 block text-sm text-muted-foreground">
+              {alt}
+            </span>
+          ) : null;
+
+          if (isPortalVideoSrc(resolved)) {
+            return (
+              <span className="mt-6 block">
+                {/* preload="metadata" so a large file is not pulled on every
+                    visit; the browser fetches it once playback starts. */}
+                <video
+                  controls
+                  preload="metadata"
+                  className="w-full rounded-[32px] border border-border bg-black"
+                >
+                  <source src={resolved} />
+                </video>
+                {caption}
+              </span>
+            );
+          }
+
+          return (
+            <span className="mt-6 block">
+              <img
+                src={resolved}
+                alt={alt ?? ""}
+                loading="lazy"
+                className="w-full rounded-[32px] border border-border"
+              />
+              {caption}
+            </span>
+          );
+        },
       }}
     >
       {children}
diff --git a/apps/edr-freight-web/portal/src/pages/support/PrivacyPolicyPage.tsx b/apps/edr-freight-web/portal/src/pages/support/PrivacyPolicyPage.tsx
index 07e79d207..a924d6514 100644
--- a/apps/edr-freight-web/portal/src/pages/support/PrivacyPolicyPage.tsx
+++ b/apps/edr-freight-web/portal/src/pages/support/PrivacyPolicyPage.tsx
@@ -1,11 +1,15 @@
 import { usePortalContent } from "@/hooks/usePortalContent";
 
 import { DocSections, DocShell } from "./DocShell";
+import { DocSidebar, useActiveSection } from "./DocSidebar";
 
 export default function PrivacyPolicyPage() {
   // Never undefined — see TermsPage.
   const { data } = usePortalContent();
   const privacy = data!.privacy;
+  const sections = privacy.sections ?? [];
+
+  const activeId = useActiveSection(sections.map((section) => section.id));
 
   return (
     <DocShell
@@ -13,8 +17,17 @@ export default function PrivacyPolicyPage() {
       title={privacy.title}
       subtitle={privacy.subtitle}
       meta={`Last updated ${privacy.lastUpdated}`}
+      sidebar={
+        <DocSidebar
+          items={sections.map((section) => ({
+            id: section.id,
+            label: section.heading,
+          }))}
+          activeId={activeId}
+        />
+      }
     >
-      <DocSections sections={privacy.sections} />
+      <DocSections sections={sections} />
     </DocShell>
   );
 }
diff --git a/apps/edr-freight-web/portal/src/pages/support/TermsPage.tsx b/apps/edr-freight-web/portal/src/pages/support/TermsPage.tsx
index 6302e838d..671882ff1 100644
--- a/apps/edr-freight-web/portal/src/pages/support/TermsPage.tsx
+++ b/apps/edr-freight-web/portal/src/pages/support/TermsPage.tsx
@@ -1,12 +1,18 @@
 import { usePortalContent } from "@/hooks/usePortalContent";
 
 import { DocSections, DocShell } from "./DocShell";
+import { DocSidebar, useActiveSection } from "./DocSidebar";
 
 export default function TermsPage() {
   // Never undefined — the hook seeds it with the shipped copy, so this public
   // page renders instantly and survives the API being unreachable.
   const { data } = usePortalContent();
   const terms = data!.terms;
+  const sections = terms.sections ?? [];
+
+  // A contents list, not a pager: the whole document stays on one page so it
+  // can be searched, printed and deep-linked to a clause.
+  const activeId = useActiveSection(sections.map((section) => section.id));
 
   return (
     <DocShell
@@ -14,8 +20,17 @@ export default function TermsPage() {
       title={terms.title}
       subtitle={terms.subtitle}
       meta={`Last updated ${terms.lastUpdated}`}
+      sidebar={
+        <DocSidebar
+          items={sections.map((section) => ({
+            id: section.id,
+            label: section.heading,
+          }))}
+          activeId={activeId}
+        />
+      }
     >
-      <DocSections sections={terms.sections} />
+      <DocSections sections={sections} />
     </DocShell>
   );
 }
diff --git a/apps/edr-freight-web/portal/src/pages/support/portal-content.test.ts b/apps/edr-freight-web/portal/src/pages/support/portal-content.test.ts
index 2523ca3ae..07b2c09b6 100644
--- a/apps/edr-freight-web/portal/src/pages/support/portal-content.test.ts
+++ b/apps/edr-freight-web/portal/src/pages/support/portal-content.test.ts
@@ -67,11 +67,16 @@ describe("withSupportVars", () => {
 });
 
 describe("safeMediaSrc", () => {
-  it("keeps same-origin paths and https sources", () => {
+  it("keeps same-origin paths and http(s) sources", () => {
     expect(safeMediaSrc("/assets/guide.webm")).toBe("/assets/guide.webm");
     expect(safeMediaSrc("https://minio.internal/support-content/a.png?sig=x")).toBe(
       "https://minio.internal/support-content/a.png?sig=x",
     );
+    // Signed object-store URLs are plain http in dev — rejecting them hid
+    // every upload.
+    expect(safeMediaSrc("http://localhost:9000/fhc/support-content/a.mp4")).toBe(
+      "http://localhost:9000/fhc/support-content/a.mp4",
+    );
   });
 
   it("drops javascript: and protocol-relative sources", () => {
diff --git a/apps/edr-freight-web/portal/src/pages/support/portal-content.ts b/apps/edr-freight-web/portal/src/pages/support/portal-content.ts
index 06bfdbce9..66c5910f8 100644
--- a/apps/edr-freight-web/portal/src/pages/support/portal-content.ts
+++ b/apps/edr-freight-web/portal/src/pages/support/portal-content.ts
@@ -90,14 +90,17 @@ export function withSupportVars(
 }
 
 /**
- * Accepts only a same-origin path or an https URL for an attached image or
- * video, returning null for anything else so the caller renders nothing.
+ * Accepts a same-origin path or an http(s) URL for an attached image or video,
+ * returning null for anything else so the caller renders nothing.
  *
- * `(?!\/)` rejects protocol-relative `//host/...`, which would otherwise pass
- * as a path. An `<img>`/`<source>` src is not a navigation, so a `javascript:`
- * URL would not execute anyway — but the guard is cheaper than re-deriving
- * that every time someone reads this file.
+ * The point is to exclude `javascript:` and `data:`, not to require TLS: the
+ * signed MinIO URLs the API hands back are plain http wherever the object
+ * store is (dev, and any deployment terminating TLS elsewhere), and rejecting
+ * those made every uploaded picture and video vanish from the page.
+ *
+ * `(?!\/)` still rejects protocol-relative `//host/...`, which would otherwise
+ * pass as a path.
  */
 export function safeMediaSrc(src: string): string | null {
-  return /^(https:\/\/|\/(?!\/))/.test(src) ? src : null;
+  return /^(https?:\/\/|\/(?!\/))/.test(src) ? src : null;
 }
diff --git a/packages/types/src/freight/portal-content.defaults.ts b/packages/types/src/freight/portal-content.defaults.ts
index 30ae3cf79..bd3ffe204 100644
--- a/packages/types/src/freight/portal-content.defaults.ts
+++ b/packages/types/src/freight/portal-content.defaults.ts
@@ -36,40 +36,29 @@ export const SUPPORT_CONTENT_DEFAULTS: SupportDocPayloadMap = {
       {
         id: "help-walkthrough",
         heading: "Portal walkthrough",
-        body: "A guided tour of the portal — registering your company, raising a booking against a contract, and settling an invoice.",
-        media: [
-          {
-            id: "help-walkthrough-video",
-            kind: "video",
-            // Ships with the app rather than MinIO, so it is used verbatim.
-            src: "/assets/edr-portal-guide.webm",
-            caption: null,
-          },
-        ],
+        // The video ships with the app rather than MinIO, so its path is used
+        // verbatim; the renderer picks <video> from the extension.
+        body: "A guided tour of the portal — registering your company, raising a booking against a contract, and settling an invoice.\n\n![](/assets/edr-portal-guide.webm)",
       },
       {
         id: "help-chat",
         heading: "Chat with our team",
         body: "Signed-in customers can open a support conversation from the headset button at the bottom right of every portal page. You can send screenshots and documents in the chat, and replies appear there and as a notification.\n\n[Open the portal](/portal)",
-        media: [],
       },
       {
         id: "help-contact",
         heading: "Contact us",
         body: "- **Email** — [{{supportEmail}}](mailto:{{supportEmail}}). Best for document issues and anything needing an attachment.\n- **Phone** — [{{supportPhone}}](tel:{{supportPhoneTel}}). Best for urgent problems with cargo already in transit.\n- **Head office** — {{supportOffice}}. Walk-in support during working hours.\n- **Support hours** — {{supportHours}}. Outside these hours, email us and we reply the next working day.",
-        media: [],
       },
       {
         id: "help-topics",
         heading: "Common topics",
         body: "- **[Account & onboarding](/faq)** — registering your company, uploading your trade licence and TIN, and getting an operational profile approved.\n- **[Contracts](/faq)** — requesting a freight contract, reviewing its terms and signing it with your saved signature and stamp.\n- **[Bookings & tracking](/faq)** — raising a booking against a contract, adding last-mile transport and following the consignment along the corridor.\n- **[Invoices & payments](/faq)** — finding invoices, paying through the bank channels and confirming a payment that has not yet settled.",
-        media: [],
       },
       {
         id: "help-checklist",
         heading: "What to include when you contact us",
         body: "- Your company name and the email you sign in with.\n- The reference of the contract, booking or invoice involved.\n- What you expected to happen and what happened instead.\n- A screenshot of any error message the portal showed.",
-        media: [],
       },
     ],
   },
diff --git a/packages/types/src/freight/portal-content.ts b/packages/types/src/freight/portal-content.ts
index 38af9e41e..104236133 100644
--- a/packages/types/src/freight/portal-content.ts
+++ b/packages/types/src/freight/portal-content.ts
@@ -38,17 +38,27 @@ export const SUPPORT_MEDIA_MAX_BYTES = 50 * 1024 * 1024;
 
 export type PortalMediaKind = "image" | "video";
 
-/** An image or video attached to a help section. */
-export interface PortalMedia {
-  id: string;
-  kind: PortalMediaKind;
-  /**
-   * Stored: a MinIO object key, a same-origin `/path`, or an `https://` URL.
-   * Served: the same value with MinIO keys replaced by a fresh presigned URL —
-   * the API rewrites this field in place, so the portal just renders it.
-   */
-  src: string;
-  caption?: string | null;
+/**
+ * Extensions the portal renders as a `<video>` rather than an `<img>`.
+ *
+ * Images and videos are both inserted with markdown's image syntax —
+ * `![caption](minio:support-content/clip.mp4)` — so an author drops media into
+ * the text in one flow and it stays where they put it. The renderer picks the
+ * element from the extension; nothing extra is stored.
+ */
+export const PORTAL_VIDEO_EXTENSIONS = [
+  ".mp4",
+  ".webm",
+  ".ogg",
+  ".ogv",
+  ".mov",
+  ".m4v",
+] as const;
+
+/** True when a media URL or key should render as a video. */
+export function isPortalVideoSrc(src: string): boolean {
+  const path = src.split(/[?#]/)[0].toLowerCase();
+  return PORTAL_VIDEO_EXTENSIONS.some((ext) => path.endsWith(ext));
 }
 
 /**
@@ -126,31 +136,19 @@ export interface PortalFaqContent {
 }
 
 /**
- * One free-form block of the help page: a heading, a full markdown body, and
- * any number of attached images or videos.
+ * Slug `HELP`. Free-form: an ordered list of sections, each a heading plus a
+ * markdown body, with images and videos embedded in the body itself.
  *
  * Deliberately not a fixed set of typed blocks (video / channels / topics /
  * checklist, as this once was). The help page is the one document whose shape
  * genuinely changes with what support needs to explain that quarter, so it is
- * built rather than filled in — add, reorder and delete sections freely.
+ * built rather than filled in — and it shares {@link PortalDocSection} with the
+ * legal documents, so every tab is edited the same way.
  */
-export interface PortalHelpSection {
-  id: string;
-  heading: string;
-  /**
-   * Markdown. Embedded images reference uploads as
-   * `![alt](minio:support-content/<file>)` — see {@link PORTAL_MEDIA_URI_SCHEME}.
-   */
-  body: string;
-  /** Rendered under the body, in order. */
-  media: PortalMedia[];
-}
-
-/** Slug `HELP`. */
 export interface PortalHelpContent {
   title: string;
   subtitle: string;
-  sections: PortalHelpSection[];
+  sections: PortalDocSection[];
 }
 
 /** Payload shape per slug — the jsonb column's type, keyed by document. */