diff --git a/packages/app/e2e/agent-timeline-pagination.spec.ts b/packages/app/e2e/agent-timeline-pagination.spec.ts
index dda0dc3a99..31d381ed27 100644
--- a/packages/app/e2e/agent-timeline-pagination.spec.ts
+++ b/packages/app/e2e/agent-timeline-pagination.spec.ts
@@ -19,6 +19,8 @@ import {
   scrollTimelineToOldestLoadedEdge,
   scrollTimelineToNewestLoadedEdge,
   seedLongMockAgentTimeline,
+  scrollThroughOlderHistoryPages,
+  seedRealisticOlderTimeline,
   sendLiveTurnBeforeHydration,
   expectTimelineViewportAnchoredAfterPrepend,
   userScrollsTimelineToHistoryStart,
@@ -48,6 +50,21 @@ test.describe("Agent timeline pagination", () => {
     }
   });
 
+  test("does not repeat an assistant block that spans older history pages", async ({ page }) => {
+    test.setTimeout(120_000);
+    const agent = await seedRealisticOlderTimeline();
+    try {
+      const history = await holdOlderHistoryPages(page, agent);
+      await openAgentTimeline(page, agent);
+      await expectTimelinePromptVisible(page, agent.newestPrompt);
+
+      await scrollThroughOlderHistoryPages(page, 3, history);
+      history.expectNoRepeatedAssistantEntries();
+    } finally {
+      await agent.cleanup();
+    }
+  });
+
   test("keeps the visible timeline position anchored while prepending a page", async ({ page }) => {
     test.setTimeout(120_000);
     const agent = await seedLongMockAgentTimeline({ turns: 80 });
diff --git a/packages/app/e2e/helpers/agent-timeline-gate.ts b/packages/app/e2e/helpers/agent-timeline-gate.ts
index 104f0a1595..3c7f7865a1 100644
--- a/packages/app/e2e/helpers/agent-timeline-gate.ts
+++ b/packages/app/e2e/helpers/agent-timeline-gate.ts
@@ -17,6 +17,7 @@ export interface AgentTimelineResponseGate {
 
 export interface OlderTimelinePagesGate {
   getRequestCount(): number;
+  getRepeatedAssistantEntryCount(): number;
   releasePage(pageNumber: number): void;
   waitForRequestCount(count: number): Promise<void>;
 }
@@ -178,6 +179,8 @@ export async function holdAgentOlderTimelinePages(
 ): Promise<OlderTimelinePagesGate> {
   let requestCount = 0;
   let responseCount = 0;
+  let repeatedAssistantEntryCount = 0;
+  const assistantEntryKeys = new Set<string>();
   const releasedPages = new Set<number>();
   const delayedForwards = new Map<number, Array<() => void>>();
   const requestWaiters = new Map<number, Array<() => void>>();
@@ -213,6 +216,26 @@ export async function holdAgentOlderTimelinePages(
         payload.direction === "before"
       ) {
         responseCount += 1;
+        const entries = Array.isArray(payload.entries) ? payload.entries : [];
+        for (const entry of entries) {
+          if (!entry || typeof entry !== "object") continue;
+          const projectedEntry = entry as {
+            seqStart?: unknown;
+            seqEnd?: unknown;
+            item?: { type?: unknown };
+          };
+          if (
+            typeof projectedEntry.seqStart !== "number" ||
+            typeof projectedEntry.seqEnd !== "number" ||
+            typeof projectedEntry.item?.type !== "string"
+          ) {
+            continue;
+          }
+          if (projectedEntry.item.type !== "assistant_message") continue;
+          const key = `${projectedEntry.seqStart}:${projectedEntry.seqEnd}:${projectedEntry.item.type}`;
+          if (assistantEntryKeys.has(key)) repeatedAssistantEntryCount += 1;
+          else assistantEntryKeys.add(key);
+        }
         const pageNumber = responseCount;
         if (releasedPages.has(pageNumber)) {
           ws.send(message);
@@ -229,6 +252,7 @@ export async function holdAgentOlderTimelinePages(
 
   return {
     getRequestCount: () => requestCount,
+    getRepeatedAssistantEntryCount: () => repeatedAssistantEntryCount,
     releasePage(pageNumber) {
       releasedPages.add(pageNumber);
       for (const forward of delayedForwards.get(pageNumber) ?? []) forward();
diff --git a/packages/app/e2e/helpers/timeline-pagination.ts b/packages/app/e2e/helpers/timeline-pagination.ts
index 7c8d15ee7f..03f0f51d0b 100644
--- a/packages/app/e2e/helpers/timeline-pagination.ts
+++ b/packages/app/e2e/helpers/timeline-pagination.ts
@@ -23,6 +23,10 @@ interface LongTimelineAgent extends MockAgentWorkspace {
   newestPrompt: string;
 }
 
+interface RealisticOlderTimelineAgent extends MockAgentWorkspace {
+  newestPrompt: string;
+}
+
 const PROMPT_PREFIX = "timeline-pagination-turn";
 const LIVE_BEFORE_HYDRATION_PROMPT = "timeline live before authoritative hydration";
 const HISTORY_START_THRESHOLD_PX = 96;
@@ -45,6 +49,7 @@ interface OlderHistoryLoadingOperation {
 interface OlderHistoryPages {
   expectRequestedPages(count: number): Promise<void>;
   expectSettledWithRequestedPages(count: number): Promise<void>;
+  expectNoRepeatedAssistantEntries(): void;
   releasePage(pageNumber: number): void;
 }
 
@@ -75,6 +80,50 @@ export async function seedLongMockAgentTimeline(
   };
 }
 
+export async function seedRealisticOlderTimeline(): Promise<RealisticOlderTimelineAgent> {
+  const agent = await seedMockAgentWorkspace({
+    repoPrefix: "timeline-realistic-older-history-",
+    title: "Realistic older timeline pagination regression",
+    model: "ten-second-stream",
+  });
+
+  const olderTurnCount = 40;
+  for (let index = 0; index < olderTurnCount; index += 1) {
+    await agent.client.sendAgentMessage(
+      agent.agentId,
+      `timeline-pagination-older-turn-${index}: emit 1 coalesced agent stream updates`,
+    );
+    await agent.client.waitForFinish(agent.agentId, 15_000);
+  }
+
+  await agent.client.sendAgentMessage(agent.agentId, "build a realistic long mock timeline");
+  await agent.client.waitForFinish(agent.agentId, 20_000);
+
+  const newerTurnCount = 20;
+  for (let index = 0; index < newerTurnCount; index += 1) {
+    await agent.client.sendAgentMessage(agent.agentId, promptForTurn(index));
+    await agent.client.waitForFinish(agent.agentId, 15_000);
+  }
+
+  return {
+    ...agent,
+    newestPrompt: promptForTurn(newerTurnCount - 1),
+  };
+}
+
+export async function scrollThroughOlderHistoryPages(
+  page: Page,
+  pageCount: number,
+  history: OlderHistoryPages,
+): Promise<void> {
+  for (let pageNumber = 0; pageNumber < pageCount; pageNumber += 1) {
+    await userScrollsTimelineToHistoryStart(page);
+    await history.expectRequestedPages(pageNumber + 1);
+    history.releasePage(pageNumber + 1);
+    await history.expectSettledWithRequestedPages(pageNumber + 1);
+  }
+}
+
 export async function rememberTimelinePromptPosition(
   page: Page,
   prompt: string,
@@ -104,7 +153,7 @@ export async function expectTimelinePromptPositionPreserved(
     .toBeLessThanOrEqual(2);
 }
 
-export async function openAgentTimeline(page: Page, agent: LongTimelineAgent): Promise<void> {
+export async function openAgentTimeline(page: Page, agent: MockAgentWorkspace): Promise<void> {
   await page.goto(buildAgentRoute(agent.workspaceId, agent.agentId));
   await page.waitForURL(
     (url) => url.pathname.includes("/workspace/") && !url.searchParams.has("open"),
@@ -204,7 +253,7 @@ export async function holdNextOlderTimelinePage(
 
 export async function holdOlderHistoryPages(
   page: Page,
-  agent: LongTimelineAgent,
+  agent: MockAgentWorkspace,
 ): Promise<OlderHistoryPages> {
   const gate: OlderTimelinePagesGate = await holdAgentOlderTimelinePages(page, agent.agentId);
   return {
@@ -216,6 +265,9 @@ export async function holdOlderHistoryPages(
       await waitForTimelineGeometryToSettle(page);
       expect(gate.getRequestCount()).toBe(count);
     },
+    expectNoRepeatedAssistantEntries() {
+      expect(gate.getRepeatedAssistantEntryCount()).toBe(0);
+    },
     releasePage(pageNumber) {
       gate.releasePage(pageNumber);
     },
diff --git a/packages/server/src/server/agent/timeline-projection.test.ts b/packages/server/src/server/agent/timeline-projection.test.ts
index 8bfbcef831..35c3156276 100644
--- a/packages/server/src/server/agent/timeline-projection.test.ts
+++ b/packages/server/src/server/agent/timeline-projection.test.ts
@@ -627,7 +627,63 @@ describe("selectProjectedTimelinePage", () => {
     });
   });
 
-  test("before page includes a wide tool whose earlier source range is before the cursor", () => {
+  test("before limit counts projected entries without repeating a merged assistant", () => {
+    const rows: AgentTimelineRow[] = [
+      ...Array.from({ length: 80 }, (_, index) => ({
+        seq: index + 1,
+        timestamp: new Date(1000 + index).toISOString(),
+        item: { type: "assistant_message" as const, text: "x" },
+      })),
+      ...Array.from({ length: 4 }, (_, index) => ({
+        seq: index + 81,
+        timestamp: new Date(2000 + index).toISOString(),
+        item: { type: "user_message" as const, text: `message ${index + 1}` },
+      })),
+    ];
+
+    const newest = selectProjectedTimelinePage({
+      rows,
+      direction: "before",
+      cursorSeq: 85,
+      limit: 2,
+    });
+    const middle = selectProjectedTimelinePage({
+      rows,
+      direction: "before",
+      cursorSeq: newest.startSeq ?? 0,
+      limit: 2,
+    });
+    const oldest = selectProjectedTimelinePage({
+      rows,
+      direction: "before",
+      cursorSeq: middle.startSeq ?? 0,
+      limit: 2,
+    });
+    const exhausted = selectProjectedTimelinePage({
+      rows,
+      direction: "before",
+      cursorSeq: oldest.startSeq ?? 0,
+      limit: 2,
+    });
+
+    const pageSummaries = [];
+    for (const page of [newest, middle, oldest]) {
+      pageSummaries.push({
+        entryTypes: page.entries.map((entry) => entry.item.type),
+        startSeq: page.startSeq,
+        endSeq: page.endSeq,
+        hasOlder: page.hasOlder,
+      });
+    }
+    expect(pageSummaries).toEqual([
+      { entryTypes: ["user_message", "user_message"], startSeq: 83, endSeq: 84, hasOlder: true },
+      { entryTypes: ["user_message", "user_message"], startSeq: 81, endSeq: 82, hasOlder: true },
+      { entryTypes: ["assistant_message"], startSeq: 1, endSeq: 80, hasOlder: false },
+    ]);
+    expect(exhausted.entries).toEqual([]);
+  });
+
+  test("before pages place a full wide tool on the page containing its projected anchor", () => {
     const rows: AgentTimelineRow[] = [
       toolRow(1, "running"),
       ...Array.from({ length: 498 }, (_, index) => ({
@@ -638,16 +694,32 @@ describe("selectProjectedTimelinePage", () => {
       toolRow(500, "completed"),
     ];
 
-    const page = selectProjectedTimelinePage({
+    const newestPage = selectProjectedTimelinePage({
       rows,
       direction: "before",
       cursorSeq: 500,
       limit: 100,
     });
+    const anchoredPage = selectProjectedTimelinePage({
+      rows,
+      direction: "before",
+      cursorSeq: 101,
+      limit: 100,
+    });
 
-    expect(page.entries.some((entry) => entry.item.type === "tool_call")).toBe(true);
-    expect(page.endSeq).toBeLessThan(500);
-    expect(page.hasOlder).toBe(true);
+    expect(newestPage.entries).toHaveLength(100);
+    expect(newestPage.entries.some((entry) => entry.item.type === "tool_call")).toBe(false);
+    expect(newestPage.startSeq).toBe(400);
+    expect(newestPage.endSeq).toBe(499);
+    expect(newestPage.hasOlder).toBe(true);
+
+    expect(anchoredPage.entries).toHaveLength(100);
+    expect(anchoredPage.entries[0]?.item.type).toBe("tool_call");
+    expect(anchoredPage.entries[0]?.seqStart).toBe(1);
+    expect(anchoredPage.entries[0]?.seqEnd).toBe(500);
+    expect(anchoredPage.startSeq).toBe(1);
+    expect(anchoredPage.endSeq).toBe(100);
+    expect(anchoredPage.hasOlder).toBe(false);
   });
 
   test("tail page includes a wide tool when its completion is the newest seq", () => {
diff --git a/packages/server/src/server/agent/timeline-projection.ts b/packages/server/src/server/agent/timeline-projection.ts
index e6bd1d1614..73c77f80fe 100644
--- a/packages/server/src/server/agent/timeline-projection.ts
+++ b/packages/server/src/server/agent/timeline-projection.ts
@@ -366,16 +366,6 @@ function getTimelineBounds(
   return { minSeq: first.seq, maxSeq: last.seq };
 }
 
-function selectEntriesOverlappingSeqRange(input: {
-  entries: readonly TimelineProjectionEntry[];
-  startSeq: number;
-  endSeq: number;
-}): TimelineProjectionEntry[] {
-  return input.entries.filter(
-    (entry) => entry.seqStart <= input.endSeq && entry.seqEnd >= input.startSeq,
-  );
-}
-
 function firstSourceSeqInRange(
   entry: TimelineProjectionEntry,
   startSeq: number,
@@ -439,6 +429,27 @@ function selectProjectedEntriesAfter(input: {
   };
 }
 
+function selectProjectedEntriesBefore(input: {
+  entries: readonly TimelineProjectionEntry[];
+  endSeq: number;
+  limit: number;
+}): { entries: TimelineProjectionEntry[]; startSeq: number | null; hasOlder: boolean } {
+  // Older history follows projected display order. Lifecycle updates can move an
+  // entry's seqEnd without moving its display anchor, so seqStart keeps the full
+  // projected item on exactly one backward page.
+  const eligible = input.entries.filter((entry) => entry.seqStart <= input.endSeq);
+  const selected =
+    input.limit === 0 || input.limit >= eligible.length
+      ? eligible
+      : eligible.slice(eligible.length - input.limit);
+
+  return {
+    entries: selected,
+    startSeq: selected[0]?.seqStart ?? null,
+    hasOlder: selected.length < eligible.length,
+  };
+}
+
 export function selectProjectedTimelinePage(input: {
   rows: readonly AgentTimelineRow[];
   bounds?: { minSeq: number; maxSeq: number };
@@ -504,11 +515,9 @@ export function selectProjectedTimelinePage(input: {
     };
   }
 
-  let startSeq: number;
-  let endSeq: number;
   if (input.direction === "after") {
     const cursorSeq = input.cursorSeq ?? bounds.minSeq - 1;
-    startSeq = Math.max(bounds.minSeq, cursorSeq + 1);
+    const startSeq = Math.max(bounds.minSeq, cursorSeq + 1);
     const selected = selectProjectedEntriesAfter({
       entries: projectedAll,
       rows: input.rows,
@@ -523,28 +532,26 @@ export function selectProjectedTimelinePage(input: {
       hasOlder: startSeq > bounds.minSeq,
       hasNewer: selected.endSeq !== null && selected.endSeq < bounds.maxSeq,
     };
-  } else {
-    const cursorSeq = input.cursorSeq ?? bounds.maxSeq + 1;
-    endSeq = Math.min(bounds.maxSeq, cursorSeq - 1);
-    startSeq = limit === 0 ? bounds.minSeq : Math.max(bounds.minSeq, cursorSeq - limit);
   }
 
-  if (startSeq > endSeq) {
+  const cursorSeq = input.cursorSeq ?? bounds.maxSeq + 1;
+  const endSeq = Math.min(bounds.maxSeq, cursorSeq - 1);
+  if (endSeq < bounds.minSeq) {
     return {
       entries: [],
       startSeq: null,
       endSeq: null,
-      hasOlder: startSeq > bounds.minSeq,
+      hasOlder: false,
       hasNewer: endSeq < bounds.maxSeq,
     };
   }
 
-  const entries = selectEntriesOverlappingSeqRange({ entries: projectedAll, startSeq, endSeq });
+  const selected = selectProjectedEntriesBefore({ entries: projectedAll, endSeq, limit });
   return {
-    entries,
-    startSeq,
+    entries: selected.entries,
+    startSeq: selected.startSeq,
     endSeq,
-    hasOlder: startSeq > bounds.minSeq,
+    hasOlder: selected.hasOlder,
     hasNewer: endSeq < bounds.maxSeq,
   };
 }