diff --git a/apps/dashboard/src/app/(dashboard)/status-pages/[id]/maintenances/(list)/page.tsx b/apps/dashboard/src/app/(dashboard)/status-pages/[id]/maintenances/(list)/page.tsx
index 0658fb2f5..fa4a2068b 100644
--- a/apps/dashboard/src/app/(dashboard)/status-pages/[id]/maintenances/(list)/page.tsx
+++ b/apps/dashboard/src/app/(dashboard)/status-pages/[id]/maintenances/(list)/page.tsx
@@ -81,7 +81,7 @@ export default function Page() {
                 await createMaintenanceMutation.mutateAsync({
                   pageId: Number.parseInt(id),
                   title: values.title,
-                  message: values.message,
+                  message: values.message ?? "",
                   startDate: values.startDate,
                   endDate: values.endDate,
                   pageComponents: values.pageComponents,
diff --git a/apps/dashboard/src/app/(dashboard)/status-pages/[id]/maintenances/[maintenanceId]/client.tsx b/apps/dashboard/src/app/(dashboard)/status-pages/[id]/maintenances/[maintenanceId]/client.tsx
index 280f84eb3..846481c4d 100644
--- a/apps/dashboard/src/app/(dashboard)/status-pages/[id]/maintenances/[maintenanceId]/client.tsx
+++ b/apps/dashboard/src/app/(dashboard)/status-pages/[id]/maintenances/[maintenanceId]/client.tsx
@@ -22,7 +22,6 @@ import { SectionGroup } from "@/components/content/section";
 import { Timeline } from "@/components/content/timeline";
 import { MaintenanceActions } from "@/components/maintenances/maintenance-actions";
 import { MaintenanceComponents } from "@/components/maintenances/maintenance-components";
-import { MaintenanceComposer } from "@/components/maintenances/maintenance-composer";
 import { MaintenanceProperties } from "@/components/maintenances/maintenance-properties";
 import { MaintenanceUpdateComposer } from "@/components/maintenances/maintenance-update-composer";
 import { MaintenanceUpdateTimelineItem } from "@/components/maintenances/maintenance-update-timeline";
@@ -99,27 +98,20 @@ export function Client({ id, pageId }: { id: number; pageId: number }) {
       </DetailHeader>
       <DetailContent>
         <DetailMain>
-          <DetailSection>
-            <DetailSectionTitle variant="heading">Message</DetailSectionTitle>
-            <MaintenanceComposer maintenance={maintenance} />
-          </DetailSection>
-          <DetailSection>
-            <DetailSectionTitle variant="heading">Updates</DetailSectionTitle>
-            <Timeline>
-              <MaintenanceUpdateComposer
+          <Timeline>
+            <MaintenanceUpdateComposer
+              maintenance={maintenance}
+              canNotify={canNotify}
+            />
+            {updates.map((update, i) => (
+              <MaintenanceUpdateTimelineItem
+                key={update.id}
                 maintenance={maintenance}
-                canNotify={canNotify}
+                update={update}
+                index={updates.length - i}
               />
-              {updates.map((update, i) => (
-                <MaintenanceUpdateTimelineItem
-                  key={update.id}
-                  maintenance={maintenance}
-                  update={update}
-                  index={updates.length - i}
-                />
-              ))}
-            </Timeline>
-          </DetailSection>
+            ))}
+          </Timeline>
         </DetailMain>
         <DetailAside>
           <DetailSection>
diff --git a/apps/dashboard/src/components/data-table/maintenances/data-table-row-actions.tsx b/apps/dashboard/src/components/data-table/maintenances/data-table-row-actions.tsx
index c6ebdffaa..9bab71caa 100644
--- a/apps/dashboard/src/components/data-table/maintenances/data-table-row-actions.tsx
+++ b/apps/dashboard/src/components/data-table/maintenances/data-table-row-actions.tsx
@@ -69,7 +69,6 @@ export function MaintenanceRowActions({
         )}
         defaultValues={{
           title: maintenance.title,
-          message: maintenance.message,
           startDate: maintenance.from,
           endDate: maintenance.to,
           pageComponents: maintenance.pageComponents?.map((c) => c.id) ?? [],
@@ -78,7 +77,6 @@ export function MaintenanceRowActions({
           await updateMaintenanceMutation.mutateAsync({
             id: maintenance.id,
             title: values.title,
-            message: values.message,
             startDate: values.startDate,
             endDate: values.endDate,
             pageComponents: values.pageComponents,
diff --git a/apps/dashboard/src/components/forms/maintenance/form.tsx b/apps/dashboard/src/components/forms/maintenance/form.tsx
index b61acbf7e..34bbefd49 100644
--- a/apps/dashboard/src/components/forms/maintenance/form.tsx
+++ b/apps/dashboard/src/components/forms/maintenance/form.tsx
@@ -46,7 +46,8 @@ import { useTRPC } from "@/lib/trpc/client";
 const schema = z
   .object({
     title: z.string().trim().min(1, "Title is required"),
-    message: z.string(),
+    /** Create only: becomes the first timeline update. */
+    message: z.string().trim().min(1, "Message is required").optional(),
     startDate: z.date(),
     endDate: z.date(),
     pageComponents: z.array(z.number()),
@@ -215,39 +216,46 @@ export function FormMaintenance({
             )}
           />
         </FormCardContent>
-        <FormCardSeparator />
-        <FormCardContent>
-          <Tabs defaultValue="tab-1">
-            <TabsList>
-              <TabsTrigger value="tab-1">Writing</TabsTrigger>
-              <TabsTrigger value="tab-2">Preview</TabsTrigger>
-            </TabsList>
-            <TabsContent value="tab-1">
-              <FormField
-                control={form.control}
-                name="message"
-                render={({ field }) => (
-                  <FormItem>
-                    <FormLabel>Message</FormLabel>
-                    <FormControl>
-                      <Textarea rows={6} {...field} />
-                    </FormControl>
-                    <FormMessage />
-                    <FormDescription>Markdown support</FormDescription>
-                  </FormItem>
-                )}
-              />
-            </TabsContent>
-            <TabsContent value="tab-2">
-              <div className="grid gap-2">
-                <Label>Preview</Label>
-                <div className="prose dark:prose-invert prose-sm text-foreground rounded-md border px-3 py-2 text-sm">
-                  <ProcessMessage value={watchMessage} />
-                </div>
-              </div>
-            </TabsContent>
-          </Tabs>
-        </FormCardContent>
+        {!defaultValues ? (
+          <>
+            <FormCardSeparator />
+            <FormCardContent>
+              <Tabs defaultValue="tab-1">
+                <TabsList>
+                  <TabsTrigger value="tab-1">Writing</TabsTrigger>
+                  <TabsTrigger value="tab-2">Preview</TabsTrigger>
+                </TabsList>
+                <TabsContent value="tab-1">
+                  <FormField
+                    control={form.control}
+                    name="message"
+                    render={({ field }) => (
+                      <FormItem>
+                        <FormLabel>Message</FormLabel>
+                        <FormControl>
+                          <Textarea rows={6} {...field} />
+                        </FormControl>
+                        <FormMessage />
+                        <FormDescription>
+                          Markdown support. Posted as the first update; later
+                          updates are added on the maintenance page.
+                        </FormDescription>
+                      </FormItem>
+                    )}
+                  />
+                </TabsContent>
+                <TabsContent value="tab-2">
+                  <div className="grid gap-2">
+                    <Label>Preview</Label>
+                    <div className="prose dark:prose-invert prose-sm text-foreground rounded-md border px-3 py-2 text-sm">
+                      <ProcessMessage value={watchMessage ?? ""} />
+                    </div>
+                  </div>
+                </TabsContent>
+              </Tabs>
+            </FormCardContent>
+          </>
+        ) : null}
         <FormCardSeparator />
         <FormCardContent>
           <FormField
diff --git a/apps/dashboard/src/components/forms/maintenance/sheet-create.tsx b/apps/dashboard/src/components/forms/maintenance/sheet-create.tsx
index 00384bd1d..c385d3c94 100644
--- a/apps/dashboard/src/components/forms/maintenance/sheet-create.tsx
+++ b/apps/dashboard/src/components/forms/maintenance/sheet-create.tsx
@@ -141,7 +141,7 @@ export function FormSheetMaintenanceCreate({
                   await createMaintenanceMutation.mutateAsync({
                     pageId,
                     title: values.title,
-                    message: values.message,
+                    message: values.message ?? "",
                     startDate: values.startDate,
                     endDate: values.endDate,
                     pageComponents: values.pageComponents,
diff --git a/apps/dashboard/src/components/maintenances/maintenance-composer.tsx b/apps/dashboard/src/components/maintenances/maintenance-composer.tsx
deleted file mode 100644
index 39d1baf60..000000000
--- a/apps/dashboard/src/components/maintenances/maintenance-composer.tsx
+++ /dev/null
@@ -1,79 +0,0 @@
-"use client";
-
-import type { RouterOutputs } from "@openstatus/api";
-import { Button } from "@openstatus/ui/components/ui/button";
-import { useState } from "react";
-import { toast } from "sonner";
-
-import {
-  Composer,
-  ComposerFooter,
-  ComposerHeader,
-  ComposerPreview,
-  ComposerTextarea,
-} from "@/components/content/composer";
-
-import { useUpdateMaintenance } from "./use-update-maintenance";
-
-type Maintenance = NonNullable<RouterOutputs["maintenance"]["get"]>;
-
-/** The single maintenance message: edit in place, save explicitly, no matter the status. */
-export function MaintenanceComposer({
-  maintenance,
-}: {
-  maintenance: Maintenance;
-}) {
-  // null = pristine: the editor follows the server copy, so a background
-  // refetch never clobbers unsaved edits.
-  const [draft, setDraft] = useState<string | null>(null);
-  const server = maintenance.message;
-  const content = draft ?? server;
-  const { update, isPending } = useUpdateMaintenance(maintenance.id, {
-    onSuccess: () => {
-      toast.success("Message saved");
-      setDraft(null);
-    },
-  });
-
-  const dirty = draft !== null && draft !== server;
-  // the service rejects an empty message
-  const canSave = dirty && content.trim().length > 0 && !isPending;
-  const submit = () => update({ message: content });
-
-  return (
-    <Composer size="lg">
-      <ComposerHeader />
-      <ComposerTextarea
-        aria-label="Message"
-        placeholder="What is being maintained and what customers can expect."
-        disabled={isPending}
-        value={content}
-        onChange={(e) => setDraft(e.target.value)}
-        onSubmit={canSave ? submit : undefined}
-      />
-      <ComposerPreview value={content} />
-      <ComposerFooter>
-        <span className="text-xs">
-          {dirty
-            ? "Unsaved changes"
-            : "Visible to everyone on your status page"}
-        </span>
-        <div className="ml-auto flex items-center gap-2">
-          {dirty ? (
-            <Button
-              size="sm"
-              variant="ghost"
-              disabled={isPending}
-              onClick={() => setDraft(null)}
-            >
-              Reset
-            </Button>
-          ) : null}
-          <Button size="sm" disabled={!canSave} onClick={submit}>
-            Save
-          </Button>
-        </div>
-      </ComposerFooter>
-    </Composer>
-  );
-}
diff --git a/apps/dashboard/src/components/maintenances/maintenance-update-composer.tsx b/apps/dashboard/src/components/maintenances/maintenance-update-composer.tsx
index 8660dc428..dc2cc08ca 100644
--- a/apps/dashboard/src/components/maintenances/maintenance-update-composer.tsx
+++ b/apps/dashboard/src/components/maintenances/maintenance-update-composer.tsx
@@ -25,7 +25,7 @@ import { usePublishMaintenanceUpdate } from "./use-publish-maintenance-update";
 
 type Maintenance = NonNullable<RouterOutputs["maintenance"]["get"]>;
 
-/** Posts a dated note on the maintenance timeline; the announcement stays as is. */
+/** Posts a dated note on the maintenance timeline; the newest is the public message. */
 export function MaintenanceUpdateComposer({
   maintenance,
   canNotify,
diff --git a/apps/dashboard/src/components/maintenances/use-update-maintenance.ts b/apps/dashboard/src/components/maintenances/use-update-maintenance.ts
index 93baf4772..5375c900c 100644
--- a/apps/dashboard/src/components/maintenances/use-update-maintenance.ts
+++ b/apps/dashboard/src/components/maintenances/use-update-maintenance.ts
@@ -47,7 +47,6 @@ export function useUpdateMaintenance(
       queryClient.setQueryData(queryKey, {
         ...maintenance,
         title: input.title,
-        message: input.message,
         from: input.startDate,
         to: input.endDate,
         pageComponentIds: input.pageComponents ?? maintenance.pageComponentIds,
diff --git a/apps/dashboard/src/data/maintenances.client.ts b/apps/dashboard/src/data/maintenances.client.ts
index 82ee52518..04d3ad714 100644
--- a/apps/dashboard/src/data/maintenances.client.ts
+++ b/apps/dashboard/src/data/maintenances.client.ts
@@ -34,7 +34,6 @@ export function toUpdateInput(maintenance: Maintenance) {
   return {
     id: maintenance.id,
     title: maintenance.title,
-    message: maintenance.message,
     startDate: maintenance.from,
     endDate: maintenance.to,
     pageComponents: maintenance.pageComponentIds,
diff --git a/apps/server/src/routes/rpc/handlers/maintenance/__tests__/maintenance.test.ts b/apps/server/src/routes/rpc/handlers/maintenance/__tests__/maintenance.test.ts
index 7b70ae368..14a78a586 100644
--- a/apps/server/src/routes/rpc/handlers/maintenance/__tests__/maintenance.test.ts
+++ b/apps/server/src/routes/rpc/handlers/maintenance/__tests__/maintenance.test.ts
@@ -835,6 +835,31 @@ describe("MaintenanceService maintenance update CRUD", () => {
     );
     expect(deleted.status).toBe(200);
     expect(await deleted.json()).toEqual({ success: true });
+
+    const firstDeleted = await connectRequest(
+      "DeleteMaintenanceUpdate",
+      { id: (await first.json()).maintenanceUpdate.id },
+      { "x-openstatus-key": authKey },
+    );
+    expect(firstDeleted.status).toBe(200);
+  });
+
+  test("refuses to delete the last update", async () => {
+    const full = await connectRequest(
+      "GetMaintenance",
+      { id: String(testMaintenanceId) },
+      { "x-openstatus-key": authKey },
+    );
+    const { updates } = (await full.json()).maintenance;
+    expect(updates).toHaveLength(1);
+
+    const res = await connectRequest(
+      "DeleteMaintenanceUpdate",
+      { id: updates[0].id },
+      { "x-openstatus-key": authKey },
+    );
+    expect(res.status).toBe(400);
+    expect((await res.json()).message).toContain("at least one update");
   });
 
   test("scopes update mutations to the authenticated workspace", async () => {
@@ -1048,12 +1073,16 @@ describe("MaintenanceService.UpdateMaintenance", () => {
 
     const data = await res.json();
     expect(data.maintenance.message).toBe("Updated maintenance message");
+    // rewrites the newest update instead of appending one
+    expect(
+      data.maintenance.updates.map((u: { message: string }) => u.message),
+    ).toEqual(["Updated maintenance message"]);
 
     // Restore original message
     await db
-      .update(maintenance)
+      .update(maintenanceUpdate)
       .set({ message: "Maintenance to update" })
-      .where(eq(maintenance.id, testMaintenanceToUpdateId));
+      .where(eq(maintenanceUpdate.maintenanceId, testMaintenanceToUpdateId));
   });
 
   test("updates page component associations", async () => {
diff --git a/apps/server/src/routes/rpc/handlers/maintenance/index.ts b/apps/server/src/routes/rpc/handlers/maintenance/index.ts
index fbfabad94..a45d94e54 100644
--- a/apps/server/src/routes/rpc/handlers/maintenance/index.ts
+++ b/apps/server/src/routes/rpc/handlers/maintenance/index.ts
@@ -57,7 +57,7 @@ export const maintenanceServiceImpl: ServiceImpl<typeof MaintenanceService> = {
       const rpcCtx = getRpcContext(ctx);
       const sCtx = toServiceCtx(rpcCtx);
 
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx: sCtx,
         input: {
           title: req.title,
diff --git a/apps/server/src/routes/v1/maintenanceUpdates/maintenance-updates.test.ts b/apps/server/src/routes/v1/maintenanceUpdates/maintenance-updates.test.ts
index 0e3e2a26c..a43a515fe 100644
--- a/apps/server/src/routes/v1/maintenanceUpdates/maintenance-updates.test.ts
+++ b/apps/server/src/routes/v1/maintenanceUpdates/maintenance-updates.test.ts
@@ -55,11 +55,13 @@ test("maintenance update REST CRUD", async () => {
       "Edited REST maintenance update",
     );
 
-    // the announcement is not a mirror of the timeline
+    // `message` is the newest update
     const parentAgain = await app.request(`/v1/maintenance/${parent.id}`, {
       headers,
     });
-    expect((await parentAgain.json()).message).toBe("announcement");
+    expect((await parentAgain.json()).message).toBe(
+      "Edited REST maintenance update",
+    );
 
     const deleted = await app.request(`/v1/maintenance_update/${update.id}`, {
       method: "DELETE",
diff --git a/apps/server/src/routes/v1/maintenances/get.ts b/apps/server/src/routes/v1/maintenances/get.ts
index 5e57e7f23..1964dc6f4 100644
--- a/apps/server/src/routes/v1/maintenances/get.ts
+++ b/apps/server/src/routes/v1/maintenances/get.ts
@@ -7,6 +7,7 @@ import { notEmpty } from "@/utils/not-empty";
 
 import type { maintenancesApi } from "./index";
 import { MaintenanceSchema, ParamsSchema } from "./schema";
+import { withLatestMessage } from "./updates";
 
 const getRoute = createRoute({
   method: "get",
@@ -37,6 +38,7 @@ export function registerGetMaintenance(api: typeof maintenancesApi) {
     const _maintenance = await db.query.maintenance.findFirst({
       with: {
         maintenancesToPageComponents: { with: { pageComponent: true } },
+        maintenanceUpdates: true,
       },
       where: and(
         eq(maintenance.id, Number(id)),
@@ -52,7 +54,7 @@ export function registerGetMaintenance(api: typeof maintenancesApi) {
     }
 
     const data = MaintenanceSchema.parse({
-      ..._maintenance,
+      ...withLatestMessage(_maintenance),
       monitorIds: _maintenance.maintenancesToPageComponents
         .map((m) => m.pageComponent.monitorId)
         .filter(notEmpty),
diff --git a/apps/server/src/routes/v1/maintenances/get_all.ts b/apps/server/src/routes/v1/maintenances/get_all.ts
index cc0e166c5..5ad76c0cd 100644
--- a/apps/server/src/routes/v1/maintenances/get_all.ts
+++ b/apps/server/src/routes/v1/maintenances/get_all.ts
@@ -7,6 +7,7 @@ import { notEmpty } from "@/utils/not-empty";
 
 import type { maintenancesApi } from "./index";
 import { MaintenanceSchema } from "./schema";
+import { withLatestMessage } from "./updates";
 
 const getAllRoute = createRoute({
   method: "get",
@@ -34,6 +35,7 @@ export function registerGetAllMaintenances(api: typeof maintenancesApi) {
     const _maintenances = await db.query.maintenance.findMany({
       with: {
         maintenancesToPageComponents: { with: { pageComponent: true } },
+        maintenanceUpdates: true,
       },
       where: eq(maintenance.workspaceId, workspaceId),
       orderBy: desc(maintenance.createdAt),
@@ -41,7 +43,7 @@ export function registerGetAllMaintenances(api: typeof maintenancesApi) {
 
     const data = MaintenanceSchema.array().parse(
       _maintenances.map((m) => ({
-        ...m,
+        ...withLatestMessage(m),
         monitorIds: m.maintenancesToPageComponents
           .map((mtm) => mtm.pageComponent.monitorId)
           .filter(notEmpty),
diff --git a/apps/server/src/routes/v1/maintenances/post.ts b/apps/server/src/routes/v1/maintenances/post.ts
index cda5177d5..f0134805b 100644
--- a/apps/server/src/routes/v1/maintenances/post.ts
+++ b/apps/server/src/routes/v1/maintenances/post.ts
@@ -2,7 +2,10 @@ import { createRoute } from "@hono/zod-openapi";
 import { Events } from "@openstatus/analytics";
 import { and, db, eq, inArray, isNull } from "@openstatus/db";
 import { monitor, page } from "@openstatus/db/src/schema";
-import { maintenance } from "@openstatus/db/src/schema/maintenances";
+import {
+  maintenance,
+  maintenanceUpdate,
+} from "@openstatus/db/src/schema/maintenances";
 import {
   maintenancesToPageComponents,
   pageComponent,
@@ -111,6 +114,18 @@ export function registerPostMaintenance(api: typeof maintenancesApi) {
         .returning()
         .get();
 
+      // the message is the first timeline update; the column is a mirror
+      await tx
+        .insert(maintenanceUpdate)
+        .values({
+          maintenanceId: newMaintenance.id,
+          message: input.message,
+          date: new Date(),
+          createdBy: actorUserId,
+          updatedBy: actorUserId,
+        })
+        .run();
+
       if (monitorIds?.length && newMaintenance.pageId) {
         // Get page components for the given monitors and page
         const pageComponents = await tx
diff --git a/apps/server/src/routes/v1/maintenances/put.ts b/apps/server/src/routes/v1/maintenances/put.ts
index c36e303e7..87698b3ca 100644
--- a/apps/server/src/routes/v1/maintenances/put.ts
+++ b/apps/server/src/routes/v1/maintenances/put.ts
@@ -19,6 +19,7 @@ import {
   dateRangeError,
   refineDateRange,
 } from "./schema";
+import { rewriteLatestUpdate, withLatestMessage } from "./updates";
 
 const putRoute = createRoute({
   method: "put",
@@ -58,7 +59,8 @@ export function registerPutMaintenance(api: typeof maintenancesApi) {
     const { id } = c.req.valid("param");
     const input = c.req.valid("json");
 
-    const { monitorIds, pageId } = input;
+    const { monitorIds, message, ...columns } = input;
+    const { pageId } = input;
 
     const _maintenance = await db.query.maintenance.findFirst({
       with: {
@@ -67,6 +69,7 @@ export function registerPutMaintenance(api: typeof maintenancesApi) {
             pageComponent: true,
           },
         },
+        maintenanceUpdates: true,
       },
       where: and(
         eq(maintenance.id, Number(id)),
@@ -131,7 +134,7 @@ export function registerPutMaintenance(api: typeof maintenancesApi) {
       const updated = await tx
         .update(maintenance)
         .set({
-          ...input,
+          ...columns,
           updatedAt: new Date(),
           updatedBy: actorUserId,
         })
@@ -139,6 +142,10 @@ export function registerPutMaintenance(api: typeof maintenancesApi) {
         .returning()
         .get();
 
+      if (message !== undefined) {
+        await rewriteLatestUpdate(tx, Number(id), message, actorUserId);
+      }
+
       if (monitorIds) {
         // Delete from maintenancesToPageComponents
         await tx
@@ -180,6 +187,7 @@ export function registerPutMaintenance(api: typeof maintenancesApi) {
 
     const data = MaintenanceSchema.parse({
       ...updatedMaintenance,
+      message: message ?? withLatestMessage(_maintenance).message,
       monitorIds:
         monitorIds ??
         _maintenance.maintenancesToPageComponents
diff --git a/apps/server/src/routes/v1/maintenances/schema.ts b/apps/server/src/routes/v1/maintenances/schema.ts
index 6ff6415cf..9ba8a97ae 100644
--- a/apps/server/src/routes/v1/maintenances/schema.ts
+++ b/apps/server/src/routes/v1/maintenances/schema.ts
@@ -25,7 +25,8 @@ export const MaintenanceObjectSchema = z.object({
     example: "Database Upgrade",
   }),
   message: z.string().openapi({
-    description: "The message describing the maintenance",
+    description:
+      "The newest timeline update. On create it becomes the first update; on update it rewrites the newest one.",
     example: "Upgrading database to improve performance",
   }),
   from: z.coerce.date().openapi({
diff --git a/apps/server/src/routes/v1/maintenances/updates.ts b/apps/server/src/routes/v1/maintenances/updates.ts
new file mode 100644
index 000000000..17e226a64
--- /dev/null
+++ b/apps/server/src/routes/v1/maintenances/updates.ts
@@ -0,0 +1,54 @@
+import { type db, desc, eq } from "@openstatus/db";
+import { maintenanceUpdate } from "@openstatus/db/src/schema/maintenances";
+import { latestMaintenanceUpdate } from "@openstatus/services/maintenance";
+
+type Tx = Parameters<Parameters<typeof db.transaction>[0]>[0];
+
+/** The public `message`: newest update, or the deprecated column. */
+export function withLatestMessage<
+  T extends {
+    message: string;
+    maintenanceUpdates: Array<{ id: number; date: Date; message: string }>;
+  },
+>(record: T): T {
+  return {
+    ...record,
+    message:
+      latestMaintenanceUpdate(record.maintenanceUpdates)?.message ??
+      record.message,
+  };
+}
+
+/** `message` on PUT edits the newest update; a bare row gets one dated now. */
+export async function rewriteLatestUpdate(
+  tx: Tx,
+  maintenanceId: number,
+  message: string,
+  actorUserId: number | null,
+): Promise<void> {
+  const latest = await tx
+    .select({ id: maintenanceUpdate.id })
+    .from(maintenanceUpdate)
+    .where(eq(maintenanceUpdate.maintenanceId, maintenanceId))
+    .orderBy(desc(maintenanceUpdate.date), desc(maintenanceUpdate.id))
+    .limit(1)
+    .get();
+  if (latest) {
+    await tx
+      .update(maintenanceUpdate)
+      .set({ message, updatedAt: new Date(), updatedBy: actorUserId })
+      .where(eq(maintenanceUpdate.id, latest.id))
+      .run();
+    return;
+  }
+  await tx
+    .insert(maintenanceUpdate)
+    .values({
+      maintenanceId,
+      message,
+      date: new Date(),
+      createdBy: actorUserId,
+      updatedBy: actorUserId,
+    })
+    .run();
+}
diff --git a/apps/server/static/openapi-v1.json b/apps/server/static/openapi-v1.json
index 49b78a75c..1cbf1496a 100644
--- a/apps/server/static/openapi-v1.json
+++ b/apps/server/static/openapi-v1.json
@@ -933,7 +933,7 @@
             "type": "string",
             "nullable": true,
             "format": "date-time",
-            "default": "2026-10-08T09:33:13.648Z",
+            "default": "2026-10-08T13:22:10.941Z",
             "description": "The date of the update in ISO8601 format"
           },
           "message": {
@@ -1014,7 +1014,7 @@
           },
           "message": {
             "type": "string",
-            "description": "The message describing the maintenance",
+            "description": "The newest timeline update. On create it becomes the first update; on update it rewrites the newest one.",
             "example": "Upgrading database to improve performance"
           },
           "from": {
@@ -6631,7 +6631,7 @@
                     "type": "string",
                     "nullable": true,
                     "format": "date-time",
-                    "default": "2026-10-08T09:33:13.648Z",
+                    "default": "2026-10-08T13:22:10.941Z",
                     "description": "The date of the report in ISO8601 format, defaults to now"
                   },
                   "message": {
@@ -7086,7 +7086,7 @@
                     "type": "string",
                     "nullable": true,
                     "format": "date-time",
-                    "default": "2026-10-08T09:33:13.648Z",
+                    "default": "2026-10-08T13:22:10.941Z",
                     "description": "The date of the update in ISO8601 format"
                   },
                   "message": {
@@ -7387,7 +7387,7 @@
                     "type": "string",
                     "nullable": true,
                     "format": "date-time",
-                    "default": "2026-10-08T09:33:13.648Z",
+                    "default": "2026-10-08T13:22:10.941Z",
                     "description": "The date of the update in ISO8601 format"
                   },
                   "message": {
@@ -8105,7 +8105,7 @@
                   },
                   "message": {
                     "type": "string",
-                    "description": "The message describing the maintenance",
+                    "description": "The newest timeline update. On create it becomes the first update; on update it rewrites the newest one.",
                     "example": "Upgrading database to improve performance"
                   },
                   "from": {
@@ -8431,7 +8431,7 @@
                   },
                   "message": {
                     "type": "string",
-                    "description": "The message describing the maintenance",
+                    "description": "The newest timeline update. On create it becomes the first update; on update it rewrites the newest one.",
                     "example": "Upgrading database to improve performance"
                   },
                   "from": {
diff --git a/apps/status-page/src/app/(status-page)/[domain]/[locale]/(public)/feed/[type]/route.ts b/apps/status-page/src/app/(status-page)/[domain]/[locale]/(public)/feed/[type]/route.ts
index 6943f19c8..389154bbb 100644
--- a/apps/status-page/src/app/(status-page)/[domain]/[locale]/(public)/feed/[type]/route.ts
+++ b/apps/status-page/src/app/(status-page)/[domain]/[locale]/(public)/feed/[type]/route.ts
@@ -87,12 +87,11 @@ export async function GET(
       const updates = [...(maintenance.maintenanceUpdates ?? [])].sort(
         (a, b) => b.date.getTime() - a.date.getTime(),
       );
-      const description = [
-        maintenance.message,
-        ...updates.map(
-          (update) => `${update.date.toISOString()}: ${update.message}`,
-        ),
-      ].join("\n\n");
+      const description = updates.length
+        ? updates
+            .map((update) => `${update.date.toISOString()}: ${update.message}`)
+            .join("\n\n")
+        : maintenance.message;
       feed.addItem({
         id: maintenanceUrl,
         title: `${statusLabel("maintenance")} - ${maintenance.title}`,
diff --git a/apps/status-page/src/app/(status-page)/[domain]/[locale]/(public)/feed/json/route.ts b/apps/status-page/src/app/(status-page)/[domain]/[locale]/(public)/feed/json/route.ts
index 7ae0daf55..2959f4dfd 100644
--- a/apps/status-page/src/app/(status-page)/[domain]/[locale]/(public)/feed/json/route.ts
+++ b/apps/status-page/src/app/(status-page)/[domain]/[locale]/(public)/feed/json/route.ts
@@ -81,7 +81,7 @@ export async function GET(
         return {
           id: maintenance.id,
           name: maintenance.title,
-          message: maintenance.message,
+          message: updates[0]?.message ?? maintenance.message,
           maintenanceUpdates: updates.map((update) => ({
             id: update.id,
             message: update.message,
diff --git a/apps/status-page/src/content/markdown/generators.test.ts b/apps/status-page/src/content/markdown/generators.test.ts
index 897753bce..bef405019 100644
--- a/apps/status-page/src/content/markdown/generators.test.ts
+++ b/apps/status-page/src/content/markdown/generators.test.ts
@@ -539,7 +539,7 @@ describe("generateMaintenance", () => {
     expect(withUrls).toContain('contact_url: "mailto:status@acme.com"');
   });
 
-  test("renders the announcement, then updates newest-first", () => {
+  test("renders updates newest-first instead of the deprecated message", () => {
     const withUpdates = {
       ...maintenance,
       maintenanceUpdates: [
@@ -554,11 +554,9 @@ describe("generateMaintenance", () => {
       ],
     } as unknown as MaintenanceDetail;
     const out = generateMaintenance(withUpdates, BASE);
-    expect(out).toContain("## Details");
+    expect(out).not.toContain("## Details");
+    expect(out).not.toContain("Brief downtime.");
     expect(out).toContain("## Updates");
-    expect(out.indexOf("Brief downtime.")).toBeLessThan(
-      out.indexOf("Work completed."),
-    );
     expect(out.indexOf("Work completed.")).toBeLessThan(
       out.indexOf("Work started."),
     );
diff --git a/apps/status-page/src/content/markdown/generators.ts b/apps/status-page/src/content/markdown/generators.ts
index 9592c294c..713c9ac7f 100644
--- a/apps/status-page/src/content/markdown/generators.ts
+++ b/apps/status-page/src/content/markdown/generators.ts
@@ -152,8 +152,9 @@ export function generateOverview(
         mdUrl(`events/maintenance/${m.id}`),
       ].filter(Boolean);
       out.push(head.join(" · "));
-      if (m.message) out.push(`  ${m.message}`);
-      for (const update of newestMaintenanceUpdates(m.maintenanceUpdates)) {
+      const updates = newestMaintenanceUpdates(m.maintenanceUpdates);
+      if (updates.length === 0 && m.message) out.push(`  ${m.message}`);
+      for (const update of updates) {
         out.push(`  - ${formatDayTime(update.date)} — ${update.message}`);
       }
     }
@@ -456,8 +457,9 @@ export function generateEventsList(
         `### [${escapeLinkLabel(m.title)}](${mdUrl(`events/maintenance/${m.id}`)})`,
       );
       out.push(meta.join(" · "));
-      if (m.message) out.push(m.message);
-      for (const update of newestMaintenanceUpdates(m.maintenanceUpdates)) {
+      const updates = newestMaintenanceUpdates(m.maintenanceUpdates);
+      if (updates.length === 0 && m.message) out.push(m.message);
+      for (const update of updates) {
         out.push(`- ${formatDayTime(update.date)} — ${update.message}`);
       }
       out.push("");
@@ -585,9 +587,8 @@ export function generateMaintenance(
     out.push(`**Affected components:** ${components.join(", ")}\n`);
   }
 
-  out.push("## Details\n");
-  out.push(`${maintenance.message}\n`);
-
+  // the oldest update is the announcement; `message` only serves rows that
+  // predate the timeline
   const updates = newestMaintenanceUpdates(maintenance.maintenanceUpdates);
   if (updates.length > 0) {
     out.push("## Updates\n");
@@ -595,6 +596,9 @@ export function generateMaintenance(
       out.push(`### ${formatDayTime(update.date)}\n`);
       out.push(`${update.message}\n`);
     }
+  } else {
+    out.push("## Details\n");
+    out.push(`${maintenance.message}\n`);
   }
 
   return `${out.join("\n").trimEnd()}\n`;
diff --git a/apps/web/src/content/pages/docs/reference/maintenance.mdx b/apps/web/src/content/pages/docs/reference/maintenance.mdx
index aacebcf50..6b6ce53bd 100644
--- a/apps/web/src/content/pages/docs/reference/maintenance.mdx
+++ b/apps/web/src/content/pages/docs/reference/maintenance.mdx
@@ -35,7 +35,7 @@ A short, human-readable name for the maintenance window.
 
 **Type:** String (required)
 
-A description of the maintenance shown to users, explaining what is happening and the expected impact. It is the announcement: progress during the window goes into [updates](#updates), which never change this field.
+The text shown to users, explaining what is happening and the expected impact. On create it is posted as the first [update](#updates); on read it is the message of the newest update; on update it rewrites the newest update. New timeline entries are added through the update endpoints, not through this field.
 
 **Example:** `"Upgrading our database to improve performance. Brief interruptions may occur."`
 
@@ -79,13 +79,13 @@ The v1 REST API does not expose this flag; it notifies subscribers automatically
 
 ## Updates
 
-A maintenance can carry an optional timeline of dated notes, for example "Work started", "Taking longer than expected" or "Completed early". Each update has:
+A maintenance is a timeline of dated notes. The first one is the announcement written at creation, later ones track progress, for example "Work started", "Taking longer than expected" or "Completed early". Each update has:
 
 - **Message** — String (required). The note shown on the status page.
 - **Date** — Datetime (optional). When the note applies. Defaults to the time it is posted.
 - **Notify** — Boolean (optional, write-only). Sends the note to status page subscribers.
 
-Updates are independent of the maintenance message: adding, editing or deleting a note never rewrites the announcement, and a maintenance with no updates is valid. Reads return them newest-first under `updates` (RPC, agent tools) or `maintenanceUpdates` (status page JSON). The public status page, feeds and Markdown render the announcement followed by its notes.
+A maintenance always keeps at least one update: deleting the last one is rejected, delete the maintenance instead. Reads return them newest-first under `updates` (RPC, agent tools) or `maintenanceUpdates` (status page JSON). The public status page, feeds and Markdown render the updates in order, oldest first on the page.
 
 ## Relationships
 
diff --git a/deno.lock b/deno.lock
index 212bdcce3..c4704b002 100644
--- a/deno.lock
+++ b/deno.lock
@@ -58,264 +58,6 @@
       "dependencies": [
         "npm:turbo@2.11.2"
       ]
-    },
-    "members": {
-      "apps/dashboard": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "apps/server": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "apps/status-page": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "apps/web": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/ai": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/api": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/db": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/emails": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/header-analysis": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/importers": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/base": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/bird-whatsapp": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/discord": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/google-chat": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/grafana-oncall": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/ms-teams": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/ntfy": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/opsgenie": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/pagerduty": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/slack": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/telegram": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/twillio-sms": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/notifications/webhook": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/services": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/status-fetcher": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/subscriptions": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/test-utils": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/theme-store": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/tinybird": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/tracker": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/upstash": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      },
-      "packages/utils": {
-        "packageJson": {
-          "dependencies": [
-            "npm:@jsr/std__expect@^1.0.19",
-            "npm:@jsr/std__testing@^1.0.19"
-          ]
-        }
-      }
     }
   }
 }
diff --git a/packages/api/src/router/maintenance.test.ts b/packages/api/src/router/maintenance.test.ts
index acbc6581f..52b5ffa79 100644
--- a/packages/api/src/router/maintenance.test.ts
+++ b/packages/api/src/router/maintenance.test.ts
@@ -128,7 +128,6 @@ test("maintenance.update rejects maintenance from another workspace", async () =
     await caller.maintenance.update({
       id: otherWorkspaceMaintenanceId,
       title: "Unauthorized Modification",
-      message: "Should not work",
       startDate: new Date(),
       endDate: new Date(Date.now() + 3_600_000),
       pageComponents: [],
@@ -162,7 +161,6 @@ test("maintenance.update succeeds for own workspace maintenance", async () => {
   await caller.maintenance.update({
     id: 1,
     title: "Updated Maintenance Title",
-    message: "Updated message",
     startDate: new Date(),
     endDate: new Date(Date.now() + 7_200_000),
     pageComponents: [1],
@@ -262,9 +260,12 @@ test("maintenance update procedures provide full CRUD", async () => {
   expect(edited.message).toBe("Edited update");
 
   const found = await caller.maintenance.get({ id: created.id });
-  expect(found.updates.map((u) => u.message)).toEqual(["Edited update"]);
-  // the announcement is independent of the timeline
-  expect(found.message).toBe("Initial update");
+  expect(found.updates.map((u) => u.message)).toEqual([
+    "Edited update",
+    "Initial update",
+  ]);
+  // `message` is the newest update
+  expect(found.message).toBe("Edited update");
 
   await caller.maintenance.deleteUpdate({ id: added.id });
   const deleted = await db.query.maintenanceUpdate.findFirst({
diff --git a/packages/api/src/router/maintenance.ts b/packages/api/src/router/maintenance.ts
index 45ede5c91..592f5e7f3 100644
--- a/packages/api/src/router/maintenance.ts
+++ b/packages/api/src/router/maintenance.ts
@@ -137,7 +137,7 @@ export const maintenanceRouter = createTRPCRouter({
     )
     .mutation(async ({ ctx, input }) => {
       try {
-        const record = await createMaintenance({
+        const { maintenance } = await createMaintenance({
           ctx: toServiceCtx(ctx),
           input: {
             title: input.title,
@@ -148,7 +148,7 @@ export const maintenanceRouter = createTRPCRouter({
             pageComponentIds: input.pageComponents ?? [],
           },
         });
-        return { ...record, notifySubscribers: input.notifySubscribers };
+        return { ...maintenance, notifySubscribers: input.notifySubscribers };
       } catch (err) {
         toTRPCError(err);
       }
@@ -160,7 +160,6 @@ export const maintenanceRouter = createTRPCRouter({
       z.object({
         id: z.number(),
         title: z.string(),
-        message: z.string(),
         startDate: z.coerce.date(),
         endDate: z.coerce.date(),
         pageComponents: z.array(z.number()).optional(),
@@ -173,7 +172,6 @@ export const maintenanceRouter = createTRPCRouter({
           input: {
             id: input.id,
             title: input.title,
-            message: input.message,
             from: input.startDate,
             to: input.endDate,
             pageComponentIds: input.pageComponents,
diff --git a/packages/db/drizzle/0092_yielding_banshee.sql b/packages/db/drizzle/0092_yielding_banshee.sql
index 7e4932f6d..337d4fc03 100644
--- a/packages/db/drizzle/0092_yielding_banshee.sql
+++ b/packages/db/drizzle/0092_yielding_banshee.sql
@@ -12,4 +12,9 @@ CREATE TABLE `maintenance_update` (
 	FOREIGN KEY (`updated_by`) REFERENCES `user`(`id`) ON UPDATE no action ON DELETE no action
 );
 --> statement-breakpoint
-CREATE INDEX `maintenance_update_maintenance_id_idx` ON `maintenance_update` (`maintenance_id`);
\ No newline at end of file
+CREATE INDEX `maintenance_update_maintenance_id_idx` ON `maintenance_update` (`maintenance_id`);
+--> statement-breakpoint
+INSERT INTO `maintenance_update` (`maintenance_id`, `message`, `date`, `created_by`, `updated_by`)
+SELECT `id`, `message`, COALESCE(`created_at`, `from`), `created_by`, `created_by`
+FROM `maintenance`
+WHERE `message` <> '';
diff --git a/packages/db/src/schema/maintenances/maintenance.ts b/packages/db/src/schema/maintenances/maintenance.ts
index 463d3953e..77429a263 100644
--- a/packages/db/src/schema/maintenances/maintenance.ts
+++ b/packages/db/src/schema/maintenances/maintenance.ts
@@ -11,6 +11,8 @@ export const maintenance = sqliteTable(
   {
     id: integer("id").primaryKey(),
     title: text("title", { length: 256 }).notNull(),
+    // deprecated: mirror of the first `maintenance_update` (backfilled in
+    // migration 0092); dropped in a follow-up
     message: text("message").notNull(),
 
     from: integer("from", { mode: "timestamp" }).notNull(),
diff --git a/packages/db/src/seed.mts b/packages/db/src/seed.mts
index b000fe463..4a17e08de 100644
--- a/packages/db/src/seed.mts
+++ b/packages/db/src/seed.mts
@@ -8,6 +8,7 @@ import {
   incidentEvent,
   monitorIncidentTable,
   maintenance,
+  maintenanceUpdate,
   maintenancesToPageComponents,
   monitor,
   notification,
@@ -405,6 +406,34 @@ async function main() {
     .onConflictDoNothing()
     .run();
 
+  // the first update is the announcement; later ones are the timeline
+  await db
+    .insert(maintenanceUpdate)
+    .values([
+      {
+        id: 1,
+        maintenanceId: 1,
+        message:
+          "We will be performing database maintenance to improve performance. Some queries may be slower during this window.",
+        date: twentyDaysAgo,
+      },
+      {
+        id: 2,
+        maintenanceId: 1,
+        message: "Maintenance completed. All queries are back to full speed.",
+        date: twentyDaysAgoPlus2Hours,
+      },
+      {
+        id: 3,
+        maintenanceId: 2,
+        message:
+          "We will be upgrading our monitoring infrastructure to the latest version. Expect brief interruptions in data collection.",
+        date: new Date(),
+      },
+    ])
+    .onConflictDoNothing()
+    .run();
+
   // Link status reports to page components
   await db
     .insert(statusReportsToPageComponents)
diff --git a/packages/proto/api/openstatus/maintenance/v1/maintenance.proto b/packages/proto/api/openstatus/maintenance/v1/maintenance.proto
index 7055dd43e..48307a19d 100644
--- a/packages/proto/api/openstatus/maintenance/v1/maintenance.proto
+++ b/packages/proto/api/openstatus/maintenance/v1/maintenance.proto
@@ -33,7 +33,7 @@ message MaintenanceSummary {
   // Title of the maintenance.
   string title = 2;
 
-  // Message describing the maintenance.
+  // Message of the newest maintenance update.
   string message = 3;
 
   // Start time of the maintenance window (RFC 3339 format).
@@ -64,7 +64,7 @@ message Maintenance {
   // Title of the maintenance.
   string title = 2;
 
-  // Message describing the maintenance.
+  // Message of the newest maintenance update.
   string message = 3;
 
   // Start time of the maintenance window (RFC 3339 format).
diff --git a/packages/proto/api/openstatus/maintenance/v1/service.proto b/packages/proto/api/openstatus/maintenance/v1/service.proto
index 72687fbaa..f5fd47536 100644
--- a/packages/proto/api/openstatus/maintenance/v1/service.proto
+++ b/packages/proto/api/openstatus/maintenance/v1/service.proto
@@ -50,7 +50,8 @@ message CreateMaintenanceRequest {
     (gnostic.openapi.v3.property) = {example: {yaml: "Database Migration"}}
   ];
 
-  // Message describing the maintenance (required).
+  // Message describing the maintenance (required). Posted as the first
+  // maintenance update.
   string message = 2 [(buf.validate.field).string.min_len = 1];
 
   // Start time of the maintenance window (RFC 3339 format, required).
@@ -128,7 +129,7 @@ message UpdateMaintenanceRequest {
     max_len: 256
   }];
 
-  // New message for the maintenance (optional).
+  // Replaces the message of the newest maintenance update (optional).
   optional string message = 3;
 
   // New start time (RFC 3339 format, optional).
diff --git a/packages/services/src/agent-tools/maintenance.ts b/packages/services/src/agent-tools/maintenance.ts
index 5d00578a5..f3e88ca52 100644
--- a/packages/services/src/agent-tools/maintenance.ts
+++ b/packages/services/src/agent-tools/maintenance.ts
@@ -135,7 +135,9 @@ const CreateMaintenanceInputShape = z.object({
   message: z
     .string()
     .min(1)
-    .describe("Public message describing the work, shown on the page."),
+    .describe(
+      "Public message describing the work; posted as the first timeline update.",
+    ),
   from: z.iso
     .datetime()
     .describe("Start time, ISO 8601 (e.g. 2026-04-30T14:00:00Z)."),
@@ -213,7 +215,7 @@ export const createMaintenanceTool: AgentTool<
     verb: "scheduled",
   },
   async run({ ctx, input }) {
-    const record = await createMaintenance({
+    const { maintenance: record } = await createMaintenance({
       ctx,
       input: {
         title: input.title,
diff --git a/packages/services/src/import/phase-writers.ts b/packages/services/src/import/phase-writers.ts
index 6ab1ef1ce..df1680842 100644
--- a/packages/services/src/import/phase-writers.ts
+++ b/packages/services/src/import/phase-writers.ts
@@ -1,6 +1,7 @@
 import { and, count, eq, isNull } from "@openstatus/db";
 import {
   maintenance,
+  maintenanceUpdate,
   maintenancesToPageComponents,
   monitor,
   page,
@@ -636,6 +637,16 @@ export async function writeMaintenancesPhase(
         continue;
       }
 
+      // the message is the first timeline update; the announcement time
+      // of imported history is unknown, so it is dated at the window start
+      await tx.insert(maintenanceUpdate).values({
+        maintenanceId: inserted.id,
+        message: data.message,
+        date: data.from,
+        createdBy: actorUserId,
+        updatedBy: actorUserId,
+      });
+
       const componentLinks: Array<{
         maintenanceId: number;
         pageComponentId: number;
diff --git a/packages/services/src/maintenance/__tests__/attribution.test.ts b/packages/services/src/maintenance/__tests__/attribution.test.ts
index b128a9bdc..bb46958ea 100644
--- a/packages/services/src/maintenance/__tests__/attribution.test.ts
+++ b/packages/services/src/maintenance/__tests__/attribution.test.ts
@@ -47,7 +47,7 @@ function range() {
 }
 
 async function create(ctx: ServiceContext, title: string) {
-  return createMaintenance({
+  const { maintenance } = await createMaintenance({
     ctx,
     input: {
       title: `${TEST_PREFIX}-${title}`,
@@ -57,6 +57,7 @@ async function create(ctx: ServiceContext, title: string) {
       pageComponentIds: [],
     },
   });
+  return maintenance;
 }
 
 describe("maintenance attribution", () => {
diff --git a/packages/services/src/maintenance/__tests__/maintenance.test.ts b/packages/services/src/maintenance/__tests__/maintenance.test.ts
index d51e8931e..64ef5b54a 100644
--- a/packages/services/src/maintenance/__tests__/maintenance.test.ts
+++ b/packages/services/src/maintenance/__tests__/maintenance.test.ts
@@ -142,7 +142,7 @@ describe("createMaintenance", () => {
     await withTestTransaction(async (tx) => {
       const ctx = { ...teamCtx, db: tx };
       const range = futureRange();
-      const record = await createMaintenance({
+      const { maintenance: record, initialUpdate } = await createMaintenance({
         ctx,
         input: {
           title: `${TEST_PREFIX}-happy`,
@@ -155,6 +155,9 @@ describe("createMaintenance", () => {
 
       expect(record.title).toBe(`${TEST_PREFIX}-happy`);
       expect(record.pageId).toBe(testPageId);
+      expect(initialUpdate.maintenanceId).toBe(record.id);
+      expect(initialUpdate.message).toBe("planned work");
+      expect(initialUpdate.createdBy).toBe(1);
 
       const assoc = await tx
         .select()
@@ -172,6 +175,13 @@ describe("createMaintenance", () => {
         entityId: record.id,
         db: tx,
       });
+      await expectAuditRow({
+        workspaceId: teamCtx.workspace.id,
+        action: "maintenance_update.create",
+        entityType: "maintenance_update",
+        entityId: initialUpdate.id,
+        db: tx,
+      });
     });
   });
 
@@ -217,7 +227,7 @@ describe("createMaintenance", () => {
       // Duplicate ids in the input would violate the composite PK on
       // `maintenances_to_page_components` if not deduped. Guard against a
       // regression where the `Set` in `validatePageComponentIds` is dropped.
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx: { ...teamCtx, db: tx },
         input: {
           title: `${TEST_PREFIX}-dedupe`,
@@ -285,7 +295,7 @@ describe("updateMaintenance", () => {
   test("updates title + replaces associations", async () => {
     await withTestTransaction(async (tx) => {
       const ctx = { ...teamCtx, db: tx };
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx,
         input: {
           title: `${TEST_PREFIX}-update`,
@@ -315,10 +325,53 @@ describe("updateMaintenance", () => {
     });
   });
 
+  test("message rewrites the newest update and audits it", async () => {
+    await withTestTransaction(async (tx) => {
+      const ctx = { ...teamCtx, db: tx };
+      const { maintenance: record, initialUpdate } = await createMaintenance({
+        ctx,
+        input: {
+          title: `${TEST_PREFIX}-update-message`,
+          message: "first",
+          ...futureRange(),
+          pageId: testPageId,
+          pageComponentIds: [],
+        },
+      });
+      const later = await addMaintenanceUpdate({
+        ctx,
+        input: {
+          maintenanceId: record.id,
+          message: "second",
+          date: new Date(Date.now() + 1000),
+        },
+      });
+
+      await updateMaintenance({
+        ctx,
+        input: { id: record.id, message: "second, edited" },
+      });
+
+      const full = await getMaintenance({ ctx, input: { id: record.id } });
+      expect(full.message).toBe("second, edited");
+      expect(full.updates.map((u) => [u.id, u.message])).toEqual([
+        [later.id, "second, edited"],
+        [initialUpdate.id, "first"],
+      ]);
+      await expectAuditRow({
+        workspaceId: teamCtx.workspace.id,
+        action: "maintenance_update.update",
+        entityType: "maintenance_update",
+        entityId: later.id,
+        db: tx,
+      });
+    });
+  });
+
   test("keeps pageId when clearing all components", async () => {
     await withTestTransaction(async (tx) => {
       const ctx = { ...teamCtx, db: tx };
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx,
         input: {
           title: `${TEST_PREFIX}-keep-page`,
@@ -347,7 +400,7 @@ describe("updateMaintenance", () => {
   test("moves pageId when components belong to another page", async () => {
     await withTestTransaction(async (tx) => {
       const ctx = { ...teamCtx, db: tx };
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx,
         input: {
           title: `${TEST_PREFIX}-move-page`,
@@ -368,7 +421,7 @@ describe("updateMaintenance", () => {
 
   test("throws NotFoundError for cross-workspace update", async () => {
     await withTestTransaction(async (tx) => {
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx: { ...teamCtx, db: tx },
         input: {
           title: `${TEST_PREFIX}-cross-ws-update`,
@@ -395,7 +448,7 @@ describe("updateMaintenance", () => {
       // `{from, to}` submissions. A partial update that moves only `to`
       // earlier than the stored `from` has to be rejected by the service's
       // own effective-range check. Regression guard for that code path.
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx,
         input: {
           title: `${TEST_PREFIX}-range-update`,
@@ -418,7 +471,7 @@ describe("updateMaintenance", () => {
   test("throws ConflictError when pageComponentIds span multiple pages", async () => {
     await withTestTransaction(async (tx) => {
       const ctx = { ...teamCtx, db: tx };
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx,
         input: {
           title: `${TEST_PREFIX}-update-mixed-pages`,
@@ -446,7 +499,7 @@ describe("deleteMaintenance", () => {
   test("cascades associations", async () => {
     await withTestTransaction(async (tx) => {
       const ctx = { ...teamCtx, db: tx };
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx,
         input: {
           title: `${TEST_PREFIX}-delete`,
@@ -474,7 +527,7 @@ describe("list / get", () => {
     await withTestTransaction(async (tx) => {
       const teamCtxTx = { ...teamCtx, db: tx };
       const freeCtxTx = { ...freeCtx, db: tx };
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx: teamCtxTx,
         input: {
           title: `${TEST_PREFIX}-isolation`,
@@ -505,7 +558,7 @@ describe("list / get", () => {
   test("list returns totalSize and enriched relations", async () => {
     await withTestTransaction(async (tx) => {
       const ctx = { ...teamCtx, db: tx };
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx,
         input: {
           title: `${TEST_PREFIX}-list-enrich`,
@@ -531,7 +584,7 @@ describe("list / get", () => {
 describe("notifyMaintenance", () => {
   test("throws when maintenance belongs to another workspace", async () => {
     await withTestTransaction(async (tx) => {
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx: { ...teamCtx, db: tx },
         input: {
           title: `${TEST_PREFIX}-notify-cross-ws`,
@@ -563,7 +616,7 @@ describe("slack actor path", () => {
         }),
         db: tx,
       };
-      const record = await createMaintenance({
+      const { maintenance: record } = await createMaintenance({
         ctx,
         input: {
           title: `${TEST_PREFIX}-slack`,
@@ -587,7 +640,7 @@ describe("slack actor path", () => {
 
 describe("maintenance updates", () => {
   async function createParent(ctx: ServiceContext, suffix: string) {
-    return createMaintenance({
+    const { maintenance } = await createMaintenance({
       ctx,
       input: {
         title: `${TEST_PREFIX}-${suffix}`,
@@ -597,6 +650,7 @@ describe("maintenance updates", () => {
         pageComponentIds: [],
       },
     });
+    return maintenance;
   }
 
   test("creates, edits, deletes, stamps attribution, touches parent, audits", async () => {
@@ -604,7 +658,7 @@ describe("maintenance updates", () => {
       const ctx = { ...teamCtx, db: tx };
       const parent = await createParent(ctx, "updates");
       const before = await getMaintenance({ ctx, input: { id: parent.id } });
-      expect(before.updates).toEqual([]);
+      expect(before.updates.map((u) => u.message)).toEqual(["announcement"]);
 
       const date = new Date("2026-06-20T00:15:00.000Z");
       const created = await addMaintenanceUpdate({
@@ -623,10 +677,14 @@ describe("maintenance updates", () => {
       expect(edited.message).toBe("work resumed");
       expect(edited.date.getTime()).toBe(date.getTime());
 
-      // the announcement is untouched by timeline writes
+      // `message` follows the newest update by date — the backdated note
+      // does not become the public message
       const full = await getMaintenance({ ctx, input: { id: parent.id } });
       expect(full.message).toBe("announcement");
-      expect(full.updates.map((u) => u.message)).toEqual(["work resumed"]);
+      expect(full.updates.map((u) => u.message)).toEqual([
+        "announcement",
+        "work resumed",
+      ]);
       expect(full.updatedBy).toBe(1);
 
       await deleteMaintenanceUpdate({ ctx, input: { id: created.id } });
@@ -653,18 +711,29 @@ describe("maintenance updates", () => {
     });
   });
 
-  test("the last update can be removed", async () => {
+  test("the last update cannot be removed", async () => {
     await withTestTransaction(async (tx) => {
       const ctx = { ...teamCtx, db: tx };
       const parent = await createParent(ctx, "last-update");
-      const only = await addMaintenanceUpdate({
+      const note = await addMaintenanceUpdate({
         ctx,
-        input: { maintenanceId: parent.id, message: "only" },
+        input: {
+          maintenanceId: parent.id,
+          message: "note",
+          date: new Date(Date.now() + 1000),
+        },
       });
-      await deleteMaintenanceUpdate({ ctx, input: { id: only.id } });
-      const full = await getMaintenance({ ctx, input: { id: parent.id } });
-      expect(full.updates).toEqual([]);
+      let full = await getMaintenance({ ctx, input: { id: parent.id } });
+      expect(full.message).toBe("note");
+
+      await deleteMaintenanceUpdate({ ctx, input: { id: note.id } });
+      full = await getMaintenance({ ctx, input: { id: parent.id } });
+      expect(full.updates).toHaveLength(1);
       expect(full.message).toBe("announcement");
+
+      await expect(
+        deleteMaintenanceUpdate({ ctx, input: { id: full.updates[0].id } }),
+      ).rejects.toBeInstanceOf(ConflictError);
     });
   });
 
@@ -736,7 +805,7 @@ describe("notifyMaintenanceUpdate", () => {
   test("throws when the update belongs to another workspace", async () => {
     await withTestTransaction(async (tx) => {
       const ctx = { ...teamCtx, db: tx };
-      const parent = await createMaintenance({
+      const { maintenance: parent } = await createMaintenance({
         ctx,
         input: {
           title: `${TEST_PREFIX}-notify-update-ws`,
@@ -762,7 +831,7 @@ describe("notifyMaintenanceUpdate", () => {
   test("returns false when the plan disables status-subscribers", async () => {
     await withTestTransaction(async (tx) => {
       const ctx = { ...teamCtx, db: tx };
-      const parent = await createMaintenance({
+      const { maintenance: parent } = await createMaintenance({
         ctx,
         input: {
           title: `${TEST_PREFIX}-notify-update-gated`,
diff --git a/packages/services/src/maintenance/create.ts b/packages/services/src/maintenance/create.ts
index dc9b3294b..de544ed7f 100644
--- a/packages/services/src/maintenance/create.ts
+++ b/packages/services/src/maintenance/create.ts
@@ -1,4 +1,4 @@
-import { maintenance } from "@openstatus/db/src/schema";
+import { maintenance, maintenanceUpdate } from "@openstatus/db/src/schema";
 
 import { emitAudit } from "../audit";
 import { requireScope } from "../auth";
@@ -8,7 +8,7 @@ import {
   withTransaction,
 } from "../context";
 import { ConflictError } from "../errors";
-import type { Maintenance } from "../types";
+import type { Maintenance, MaintenanceUpdate } from "../types";
 import {
   assertPageInWorkspace,
   updatePageComponentAssociations,
@@ -16,10 +16,15 @@ import {
 } from "./internal";
 import { CreateMaintenanceInput } from "./schemas";
 
+export type CreateMaintenanceResult = {
+  maintenance: Maintenance;
+  initialUpdate: MaintenanceUpdate;
+};
+
 export async function createMaintenance(args: {
   ctx: ServiceContext;
   input: CreateMaintenanceInput;
-}): Promise<Maintenance> {
+}): Promise<CreateMaintenanceResult> {
   const { ctx } = args;
   requireScope(ctx, "write");
   const input = CreateMaintenanceInput.parse(args.input);
@@ -50,6 +55,7 @@ export async function createMaintenance(args: {
         workspaceId: ctx.workspace.id,
         pageId: input.pageId,
         title: input.title,
+        // deprecated column: mirrors the first update until it is dropped
         message: input.message,
         from: input.from,
         to: input.to,
@@ -65,6 +71,18 @@ export async function createMaintenance(args: {
       componentIds: validated.componentIds,
     });
 
+    const initialUpdate = await tx
+      .insert(maintenanceUpdate)
+      .values({
+        maintenanceId: record.id,
+        message: input.message,
+        date: input.date ?? new Date(),
+        createdBy: actorUserId,
+        updatedBy: actorUserId,
+      })
+      .returning()
+      .get();
+
     await emitAudit(tx, ctx, {
       action: "maintenance.create",
       entityType: "maintenance",
@@ -72,6 +90,14 @@ export async function createMaintenance(args: {
       after: record,
     });
 
-    return record;
+    await emitAudit(tx, ctx, {
+      action: "maintenance_update.create",
+      entityType: "maintenance_update",
+      entityId: initialUpdate.id,
+      after: initialUpdate,
+      metadata: { maintenanceId: record.id },
+    });
+
+    return { maintenance: record, initialUpdate };
   });
 }
diff --git a/packages/services/src/maintenance/delete-update.ts b/packages/services/src/maintenance/delete-update.ts
index 26230b13e..f44ec5308 100644
--- a/packages/services/src/maintenance/delete-update.ts
+++ b/packages/services/src/maintenance/delete-update.ts
@@ -1,4 +1,4 @@
-import { eq } from "@openstatus/db";
+import { eq, sql } from "@openstatus/db";
 import { maintenanceUpdate } from "@openstatus/db/src/schema";
 
 import { emitAudit } from "../audit";
@@ -8,6 +8,7 @@ import {
   tryGetActorUserId,
   withTransaction,
 } from "../context";
+import { ConflictError } from "../errors";
 import { touchMaintenance } from "./add-update";
 import { getMaintenanceUpdateInWorkspace } from "./internal";
 import { DeleteMaintenanceUpdateInput } from "./schemas";
@@ -28,6 +29,18 @@ export async function deleteMaintenanceUpdate(args: {
       workspaceId: ctx.workspace.id,
     });
 
+    // the newest update is the maintenance's public message
+    const remaining = await tx
+      .select({ count: sql<number>`count(*)` })
+      .from(maintenanceUpdate)
+      .where(eq(maintenanceUpdate.maintenanceId, existing.maintenanceId))
+      .get();
+    if ((remaining?.count ?? 0) <= 1) {
+      throw new ConflictError(
+        "A maintenance needs at least one update. Delete the maintenance instead.",
+      );
+    }
+
     await tx
       .delete(maintenanceUpdate)
       .where(eq(maintenanceUpdate.id, existing.id));
diff --git a/packages/services/src/maintenance/index.ts b/packages/services/src/maintenance/index.ts
index e38fef64f..f8066e7c6 100644
--- a/packages/services/src/maintenance/index.ts
+++ b/packages/services/src/maintenance/index.ts
@@ -1,5 +1,5 @@
 export { addMaintenanceUpdate } from "./add-update";
-export { createMaintenance } from "./create";
+export { type CreateMaintenanceResult, createMaintenance } from "./create";
 export { deleteMaintenance } from "./delete";
 export { deleteMaintenanceUpdate } from "./delete-update";
 export { getMaintenanceUpdate } from "./get-update";
@@ -14,6 +14,7 @@ export { notifyMaintenance } from "./notify";
 export { notifyMaintenanceUpdate } from "./notify-update";
 export { updateMaintenance } from "./update";
 export { updateMaintenanceUpdate } from "./update-update";
+export { latestMaintenanceUpdate } from "./utils";
 
 export {
   AddMaintenanceUpdateInput,
diff --git a/packages/services/src/maintenance/list.ts b/packages/services/src/maintenance/list.ts
index 711b82d20..793aca2ca 100644
--- a/packages/services/src/maintenance/list.ts
+++ b/packages/services/src/maintenance/list.ts
@@ -26,6 +26,7 @@ import {
   ListMaintenancesInput,
   type MaintenanceListPeriod,
 } from "./schemas";
+import { latestMaintenanceUpdate } from "./utils";
 
 function periodToSince(period: MaintenanceListPeriod): Date {
   const day = 24 * 60 * 60 * 1000;
@@ -48,6 +49,7 @@ type Attributed = {
 export type MaintenanceUpdateWithRelations = MaintenanceUpdate & Attributed;
 
 export type MaintenanceWithRelations = Maintenance & {
+  /** Newest first. `message` on the row is the newest update's text. */
   updates: MaintenanceUpdateWithRelations[];
   pageComponents: PageComponent[];
   pageComponentIds: number[];
@@ -131,9 +133,12 @@ async function enrichMaintenancesBatch(
 
   return rows.map((r) => {
     const components = componentsByMaintenance.get(r.id) ?? [];
+    const updates = updatesByMaintenance.get(r.id) ?? [];
     return {
       ...r,
-      updates: updatesByMaintenance.get(r.id) ?? [],
+      // the column is a stale mirror of the first update
+      message: latestMaintenanceUpdate(updates)?.message ?? r.message,
+      updates,
       pageComponents: components,
       pageComponentIds: components.map((c) => c.id),
       ...attributed(r),
diff --git a/packages/services/src/maintenance/schemas.ts b/packages/services/src/maintenance/schemas.ts
index 7263541b6..4826ac024 100644
--- a/packages/services/src/maintenance/schemas.ts
+++ b/packages/services/src/maintenance/schemas.ts
@@ -13,7 +13,10 @@ export const maintenanceListPeriodSchema = z.enum(maintenanceListPeriods);
 export const CreateMaintenanceInput = z
   .object({
     title: z.string().trim().min(1).max(256),
+    /** Becomes the first timeline update. */
     message: z.string().min(1),
+    /** Date of the first update; defaults to now. */
+    date: z.coerce.date().optional(),
     from: z.coerce.date(),
     to: z.coerce.date(),
     pageId: z.number().int(),
@@ -28,6 +31,7 @@ export type CreateMaintenanceInput = z.infer<typeof CreateMaintenanceInput>;
 export const UpdateMaintenanceInput = z.object({
   id: z.number().int(),
   title: z.string().trim().min(1).max(256).optional(),
+  /** Rewrites the newest timeline update. */
   message: z.string().min(1).optional(),
   from: z.coerce.date().optional(),
   to: z.coerce.date().optional(),
diff --git a/packages/services/src/maintenance/update.ts b/packages/services/src/maintenance/update.ts
index 34b81aede..cd848df5b 100644
--- a/packages/services/src/maintenance/update.ts
+++ b/packages/services/src/maintenance/update.ts
@@ -1,9 +1,10 @@
-import { eq } from "@openstatus/db";
-import { maintenance } from "@openstatus/db/src/schema";
+import { desc, eq } from "@openstatus/db";
+import { maintenance, maintenanceUpdate } from "@openstatus/db/src/schema";
 
 import { emitAudit } from "../audit";
 import { requireScope } from "../auth";
 import {
+  type DB,
   type ServiceContext,
   tryGetActorUserId,
   withTransaction,
@@ -24,6 +25,7 @@ export async function updateMaintenance(args: {
   const { ctx } = args;
   requireScope(ctx, "write");
   const input = UpdateMaintenanceInput.parse(args.input);
+  const actorUserId = tryGetActorUserId(ctx.actor);
 
   return withTransaction(ctx, async (tx) => {
     const existing = await getMaintenanceInWorkspace({
@@ -42,10 +44,9 @@ export async function updateMaintenance(args: {
 
     const updateValues: Record<string, unknown> = {
       updatedAt: new Date(),
-      updatedBy: tryGetActorUserId(ctx.actor),
+      updatedBy: actorUserId,
     };
     if (input.title !== undefined) updateValues.title = input.title;
-    if (input.message !== undefined) updateValues.message = input.message;
     if (input.from !== undefined) updateValues.from = input.from;
     if (input.to !== undefined) updateValues.to = input.to;
 
@@ -71,6 +72,10 @@ export async function updateMaintenance(args: {
       });
     }
 
+    if (input.message !== undefined) {
+      await rewriteLatestUpdate(tx, ctx, existing.id, input.message);
+    }
+
     const updated = await tx
       .update(maintenance)
       .set(updateValues)
@@ -95,3 +100,67 @@ export async function updateMaintenance(args: {
     return updated;
   });
 }
+
+/**
+ * `message` is the newest update's text, so editing it rewrites that row.
+ * A maintenance without updates (pre-backfill) gets one dated now instead.
+ */
+async function rewriteLatestUpdate(
+  tx: DB,
+  ctx: ServiceContext,
+  maintenanceId: number,
+  message: string,
+): Promise<void> {
+  const actorUserId = tryGetActorUserId(ctx.actor);
+  const latest = await tx
+    .select()
+    .from(maintenanceUpdate)
+    .where(eq(maintenanceUpdate.maintenanceId, maintenanceId))
+    .orderBy(desc(maintenanceUpdate.date), desc(maintenanceUpdate.id))
+    .limit(1)
+    .get();
+
+  if (!latest) {
+    const created = await tx
+      .insert(maintenanceUpdate)
+      .values({
+        maintenanceId,
+        message,
+        date: new Date(),
+        createdBy: actorUserId,
+        updatedBy: actorUserId,
+      })
+      .returning()
+      .get();
+    await emitAudit(tx, ctx, {
+      action: "maintenance_update.create",
+      entityType: "maintenance_update",
+      entityId: created.id,
+      after: created,
+      metadata: { maintenanceId },
+    });
+    return;
+  }
+
+  if (latest.message === message) return;
+
+  const updated = await tx
+    .update(maintenanceUpdate)
+    .set({ message, updatedAt: new Date(), updatedBy: actorUserId })
+    .where(eq(maintenanceUpdate.id, latest.id))
+    .returning()
+    .get();
+  if (!updated) {
+    throw new InternalServiceError(
+      `failed to update maintenance update ${latest.id}`,
+    );
+  }
+  await emitAudit(tx, ctx, {
+    action: "maintenance_update.update",
+    entityType: "maintenance_update",
+    entityId: updated.id,
+    before: latest,
+    after: updated,
+    metadata: { maintenanceId },
+  });
+}
diff --git a/packages/services/src/maintenance/utils.ts b/packages/services/src/maintenance/utils.ts
new file mode 100644
index 000000000..78cb7618e
--- /dev/null
+++ b/packages/services/src/maintenance/utils.ts
@@ -0,0 +1,18 @@
+import type { MaintenanceUpdate } from "../types";
+
+/** Newest entry by date, then id; the public `message` of a maintenance. */
+export function latestMaintenanceUpdate<
+  T extends Pick<MaintenanceUpdate, "date" | "id">,
+>(updates: ReadonlyArray<T>): T | undefined {
+  let latest: T | undefined;
+  for (const update of updates) {
+    if (
+      !latest ||
+      update.date.getTime() > latest.date.getTime() ||
+      (update.date.getTime() === latest.date.getTime() && update.id > latest.id)
+    ) {
+      latest = update;
+    }
+  }
+  return latest;
+}
diff --git a/packages/subscriptions/src/dispatcher.ts b/packages/subscriptions/src/dispatcher.ts
index a71607b28..caebca7de 100644
--- a/packages/subscriptions/src/dispatcher.ts
+++ b/packages/subscriptions/src/dispatcher.ts
@@ -96,6 +96,10 @@ export async function dispatchMaintenance(maintenanceId: number) {
       maintenancesToPageComponents: {
         with: { pageComponent: true },
       },
+      maintenanceUpdates: {
+        orderBy: (updates, { desc }) => [desc(updates.date), desc(updates.id)],
+        limit: 1,
+      },
     },
   });
 
@@ -118,7 +122,8 @@ export async function dispatchMaintenance(maintenanceId: number) {
     pageId: record.pageId,
     title: record.title,
     status: "maintenance",
-    message: record.message,
+    // the column is a stale mirror of the first update
+    message: record.maintenanceUpdates[0]?.message ?? record.message,
     pageComponentIds: pageComponents.map((c) => c.id),
     pageComponents: pageComponents.map((c) => c.name),
     date: record.from.toISOString(),
diff --git a/packages/ui/src/components/blocks/status-events.tsx b/packages/ui/src/components/blocks/status-events.tsx
index ed6c95bf4..a992b02ab 100644
--- a/packages/ui/src/components/blocks/status-events.tsx
+++ b/packages/ui/src/components/blocks/status-events.tsx
@@ -648,7 +648,8 @@ export function StatusEventTimelineReportUpdate({
 
 interface StatusMaintenanceUpdate {
   title: string;
-  message: string;
+  /** Fallback body when no `maintenanceUpdates` are given. */
+  message?: string;
   from: Date;
   to: Date;
   maintenanceUpdates?: {
@@ -660,7 +661,9 @@ interface StatusMaintenanceUpdate {
 /**
  * StatusEventTimelineMaintenance - Timeline entry for maintenance windows
  *
- * Displays a maintenance window with title, date range, duration, and message.
+ * Displays a maintenance window with title, date range and duration. The
+ * oldest update is the announcement and later ones follow as dated notes;
+ * `message` is only used when no updates are given.
  * Uses a blue dot indicator to distinguish from incident updates.
  *
  * The date range is formatted and split to allow individual StatusTimestamp
@@ -701,10 +704,11 @@ export function StatusEventTimelineMaintenance({
     maintenance.from,
     maintenance.to,
   );
-  // chronological: the announcement is the oldest event, notes follow it
-  const updates = [...(maintenance.maintenanceUpdates ?? [])].sort(
-    (a, b) => a.date.getTime() - b.date.getTime(),
-  );
+  // chronological: the oldest update is the announcement, notes follow it
+  const [announcement, ...updates] = [
+    ...(maintenance.maintenanceUpdates ?? []),
+  ].sort((a, b) => a.date.getTime() - b.date.getTime());
+  const body = announcement?.message ?? maintenance.message ?? "";
   const renderBody = (message: string) =>
     message.trim() === "" ? (
       <span className="text-muted-foreground/70">-</span>
@@ -749,7 +753,7 @@ export function StatusEventTimelineMaintenance({
             ) : null}
           </StatusEventTimelineTitle>
           <StatusEventTimelineMessage>
-            {renderBody(maintenance.message)}
+            {renderBody(body)}
           </StatusEventTimelineMessage>
         </div>
       </div>
diff --git a/packages/ui/src/components/blocks/status.types.ts b/packages/ui/src/components/blocks/status.types.ts
index 2b8d9ea36..6ba464b4f 100644
--- a/packages/ui/src/components/blocks/status.types.ts
+++ b/packages/ui/src/components/blocks/status.types.ts
@@ -35,7 +35,8 @@ export interface Maintenance {
   id: number;
   title: string;
   affected: string[];
-  message: string;
+  /** Fallback body when no `maintenanceUpdates` are given. */
+  message?: string;
   maintenanceUpdates?: {
     date: Date;
     message: string;