diff --git a/ui/src/components/IssueDocumentsSection.tsx b/ui/src/components/IssueDocumentsSection.tsx
index c3f0a9d783f..44de75192af 100644
--- a/ui/src/components/IssueDocumentsSection.tsx
+++ b/ui/src/components/IssueDocumentsSection.tsx
@@ -12,6 +12,7 @@ import { useLocation } from "@/lib/router";
 import { ApiError } from "../api/client";
 import { issuesApi } from "../api/issues";
 import { useAutosaveIndicator } from "../hooks/useAutosaveIndicator";
+import { deriveDocumentRevisionState } from "../lib/document-revisions";
 import { queryKeys } from "../lib/queryKeys";
 import { cn, relativeTime } from "../lib/utils";
 import { MarkdownBody } from "./MarkdownBody";
@@ -787,7 +788,9 @@ export function IssueDocumentsSection({
           const activeDraft = draft?.key === doc.key && !draft.isNew ? draft : null;
           const activeConflict = documentConflict?.key === doc.key ? documentConflict : null;
           const isFolded = foldedDocumentKeys.includes(doc.key);
-          const revisionHistory = getDocumentRevisions(doc.key);
+          const revisionState = deriveDocumentRevisionState(doc, getDocumentRevisions(doc.key));
+          const revisionHistory = revisionState.revisions;
+          const currentRevision = revisionState.currentRevision;
           const selectedRevisionId = selectedRevisionIds[doc.key] ?? null;
           const selectedHistoricalRevision = selectedRevisionId
             ? revisionHistory.find((revision) => revision.id === selectedRevisionId) ?? null
@@ -795,10 +798,10 @@ export function IssueDocumentsSection({
           const isHistoricalPreview = Boolean(selectedHistoricalRevision);
           const displayedTitle = selectedHistoricalRevision
             ? selectedHistoricalRevision.title ?? ""
-            : activeDraft?.title ?? doc.title ?? "";
-          const displayedBody = selectedHistoricalRevision?.body ?? activeDraft?.body ?? doc.body;
-          const displayedRevisionNumber = selectedHistoricalRevision?.revisionNumber ?? doc.latestRevisionNumber;
-          const displayedUpdatedAt = selectedHistoricalRevision?.createdAt ?? doc.updatedAt;
+            : activeDraft?.title ?? currentRevision.title ?? "";
+          const displayedBody = selectedHistoricalRevision?.body ?? activeDraft?.body ?? currentRevision.body;
+          const displayedRevisionNumber = selectedHistoricalRevision?.revisionNumber ?? currentRevision.revisionNumber;
+          const displayedUpdatedAt = selectedHistoricalRevision?.createdAt ?? currentRevision.createdAt;
           const showTitle = !isPlanKey(doc.key) && !!displayedTitle.trim() && !titlesMatchKey(displayedTitle, doc.key);
           const canVoteOnDocument = Boolean(doc.latestRevisionId && doc.updatedByAgentId && !doc.updatedByUserId && onVote);
 
@@ -848,9 +851,9 @@ export function IssueDocumentsSection({
                         {revisionMenuOpenKey === doc.key && isFetchingDocumentRevisions && revisionHistory.length === 0 ? (
                           <DropdownMenuItem disabled>Loading revisions...</DropdownMenuItem>
                         ) : revisionHistory.length > 0 ? (
-                          <DropdownMenuRadioGroup value={selectedRevisionId ?? doc.latestRevisionId ?? ""}>
+                          <DropdownMenuRadioGroup value={selectedRevisionId ?? currentRevision.id ?? ""}>
                             {revisionHistory.map((revision) => {
-                              const isCurrentRevision = revision.id === doc.latestRevisionId;
+                              const isCurrentRevision = revision.id === currentRevision.id;
                               return (
                                 <DropdownMenuRadioItem
                                   key={revision.id}
diff --git a/ui/src/lib/document-revisions.test.ts b/ui/src/lib/document-revisions.test.ts
new file mode 100644
index 00000000000..26693b40bf7
--- /dev/null
+++ b/ui/src/lib/document-revisions.test.ts
@@ -0,0 +1,83 @@
+import type { DocumentRevision, IssueDocument } from "@paperclipai/shared";
+import { describe, expect, it } from "vitest";
+import { deriveDocumentRevisionState } from "./document-revisions";
+
+function createDocument(overrides: Partial<IssueDocument> = {}): IssueDocument {
+  return {
+    id: "document-1",
+    companyId: "company-1",
+    issueId: "issue-1",
+    key: "plan",
+    title: "Plan",
+    format: "markdown",
+    body: "# Current plan",
+    latestRevisionId: "revision-2",
+    latestRevisionNumber: 2,
+    createdByAgentId: "agent-1",
+    createdByUserId: null,
+    updatedByAgentId: "agent-1",
+    updatedByUserId: null,
+    createdAt: new Date("2026-04-10T15:00:00.000Z"),
+    updatedAt: new Date("2026-04-10T16:00:00.000Z"),
+    ...overrides,
+  };
+}
+
+function createRevision(overrides: Partial<DocumentRevision> = {}): DocumentRevision {
+  return {
+    id: "revision-1",
+    companyId: "company-1",
+    documentId: "document-1",
+    issueId: "issue-1",
+    key: "plan",
+    revisionNumber: 1,
+    title: "Plan",
+    format: "markdown",
+    body: "# Revision body",
+    changeSummary: null,
+    createdByAgentId: "agent-1",
+    createdByUserId: null,
+    createdAt: new Date("2026-04-10T15:00:00.000Z"),
+    ...overrides,
+  };
+}
+
+describe("deriveDocumentRevisionState", () => {
+  it("sorts fetched revisions newest-first even when the API payload is out of order", () => {
+    const state = deriveDocumentRevisionState(createDocument(), [
+      createRevision({ id: "revision-1", revisionNumber: 1, createdAt: new Date("2026-04-10T15:00:00.000Z") }),
+      createRevision({ id: "revision-2", revisionNumber: 2, body: "# Current plan", createdAt: new Date("2026-04-10T16:00:00.000Z") }),
+    ]);
+
+    expect(state.currentRevision.id).toBe("revision-2");
+    expect(state.revisions.map((revision) => revision.id)).toEqual(["revision-2", "revision-1"]);
+  });
+
+  it("keeps the latest document revision current when the revision history cache is stale", () => {
+    const state = deriveDocumentRevisionState(createDocument(), [
+      createRevision({ id: "revision-1", revisionNumber: 1, body: "# Original plan" }),
+    ]);
+
+    expect(state.currentRevision.id).toBe("revision-2");
+    expect(state.currentRevision.body).toBe("# Current plan");
+    expect(state.revisions.map((revision) => revision.id)).toEqual(["revision-2", "revision-1"]);
+  });
+
+  it("trusts the fetched revision history when it is newer than the document summary cache", () => {
+    const staleDocument = createDocument({
+      body: "# Original plan",
+      latestRevisionId: "revision-1",
+      latestRevisionNumber: 1,
+      updatedAt: new Date("2026-04-10T15:00:00.000Z"),
+    });
+
+    const state = deriveDocumentRevisionState(staleDocument, [
+      createRevision({ id: "revision-2", revisionNumber: 2, body: "# Current plan", createdAt: new Date("2026-04-10T16:00:00.000Z") }),
+      createRevision({ id: "revision-1", revisionNumber: 1, body: "# Original plan", createdAt: new Date("2026-04-10T15:00:00.000Z") }),
+    ]);
+
+    expect(state.currentRevision.id).toBe("revision-2");
+    expect(state.currentRevision.body).toBe("# Current plan");
+    expect(state.revisions.map((revision) => revision.id)).toEqual(["revision-2", "revision-1"]);
+  });
+});
diff --git a/ui/src/lib/document-revisions.ts b/ui/src/lib/document-revisions.ts
new file mode 100644
index 00000000000..5759d4af300
--- /dev/null
+++ b/ui/src/lib/document-revisions.ts
@@ -0,0 +1,72 @@
+import type { DocumentRevision, IssueDocument } from "@paperclipai/shared";
+
+type DocumentRevisionState = {
+  currentRevision: DocumentRevision;
+  revisions: DocumentRevision[];
+};
+
+function toTimestamp(value: Date | string | null | undefined) {
+  if (!value) return 0;
+  const timestamp = new Date(value).getTime();
+  return Number.isNaN(timestamp) ? 0 : timestamp;
+}
+
+function sortRevisionsDescending(revisions: DocumentRevision[]) {
+  return [...revisions].sort((a, b) => {
+    if (a.revisionNumber !== b.revisionNumber) {
+      return b.revisionNumber - a.revisionNumber;
+    }
+    const createdAtDelta = toTimestamp(b.createdAt) - toTimestamp(a.createdAt);
+    if (createdAtDelta !== 0) return createdAtDelta;
+    return b.id.localeCompare(a.id);
+  });
+}
+
+function createCurrentRevisionSnapshot(document: IssueDocument): DocumentRevision {
+  return {
+    id: document.latestRevisionId ?? `${document.id}-latest`,
+    companyId: document.companyId,
+    documentId: document.id,
+    issueId: document.issueId,
+    key: document.key,
+    revisionNumber: document.latestRevisionNumber,
+    title: document.title,
+    format: document.format,
+    body: document.body,
+    changeSummary: null,
+    createdByAgentId: document.updatedByAgentId ?? document.createdByAgentId,
+    createdByUserId: document.updatedByUserId ?? document.createdByUserId,
+    createdAt: document.updatedAt,
+  };
+}
+
+export function deriveDocumentRevisionState(
+  document: IssueDocument,
+  revisions: DocumentRevision[],
+): DocumentRevisionState {
+  const sortedRevisions = sortRevisionsDescending(revisions);
+  const currentSnapshot = createCurrentRevisionSnapshot(document);
+  const highestFetchedRevision = sortedRevisions[0] ?? null;
+  const documentAppearsStale = Boolean(
+    highestFetchedRevision && highestFetchedRevision.revisionNumber > document.latestRevisionNumber,
+  );
+
+  const currentRevision = documentAppearsStale
+    ? highestFetchedRevision!
+    : sortedRevisions.find((revision) => revision.id === document.latestRevisionId) ?? currentSnapshot;
+
+  const revisionsWithCurrent = sortRevisionsDescending([currentRevision, ...sortedRevisions]);
+  const dedupedRevisions: DocumentRevision[] = [];
+  const seenRevisionIds = new Set<string>();
+
+  for (const revision of revisionsWithCurrent) {
+    if (seenRevisionIds.has(revision.id)) continue;
+    seenRevisionIds.add(revision.id);
+    dedupedRevisions.push(revision);
+  }
+
+  return {
+    currentRevision,
+    revisions: dedupedRevisions,
+  };
+}