diff --git a/packages/app/e2e/browser/chat-find.spec.ts b/packages/app/e2e/browser/chat-find.spec.ts
index dd00f93216..7ed957f513 100644
--- a/packages/app/e2e/browser/chat-find.spec.ts
+++ b/packages/app/e2e/browser/chat-find.spec.ts
@@ -139,14 +139,14 @@ test("loads older history through prompt navigation and finds repeated rendered
     await expect(page.getByText("Prompt number 0", { exact: true })).toHaveCount(0);
     await searchChat(page, "hello world");
     await expectHighlight(page, "hello world");
-    await expect(status(page)).toHaveText("1 of 2 in message");
+    await expect(status(page)).toHaveText("1 of 90");
     await page.screenshot({ path: testInfo.outputPath("chat-find-highlight.png") });
     expect(jumps.requests()[0]).toMatchObject({ limit: 40, mergeWindow: true });
     await nextMatch(page);
-    await expect(status(page)).toHaveText("2 of 2 in message");
+    await expect(status(page)).toHaveText("2 of 90");
     await expectHighlight(page, "hello world");
     await previousMatch(page);
-    await expect(status(page)).toHaveText("1 of 2 in message");
+    await expect(status(page)).toHaveText("1 of 90");
     await query(page).fill("hello & world");
     await expectHighlight(page, "hello & world");
     await query(page).fill("a.b");
@@ -159,6 +159,65 @@ test("loads older history through prompt navigation and finds repeated rendered
   }
 });
 
+// The scope of the search is the whole chat, so the counter is the position across
+// every message that holds a hit, and Next walks off the end of one into the next.
+const ACROSS_PROMPT = "Find scope-needle in this chat";
+const ACROSS_RESPONSE = "Reply with scope-needle here.\n\nAnd scope-needle again there.";
+
+/** The test id of the message that holds the current match, so it can be watched crossing one. */
+async function highlightedMessage(page: Page) {
+  return page.evaluate(() => {
+    const entry = Array.from(CSS.highlights.entries()).find(([name]) =>
+      name.startsWith("paseo-chat-find-"),
+    );
+    const range = entry && Array.from(entry[1])[0];
+    if (!(range instanceof Range)) return null;
+    const message = range.startContainer.parentElement?.closest<HTMLElement>(
+      '[data-testid="user-message"], [data-testid="assistant-message"]',
+    );
+    return message?.dataset.testid ?? null;
+  });
+}
+async function expectHighlightedMessage(page: Page, testId: string) {
+  await expect.poll(() => highlightedMessage(page)).toBe(testId);
+}
+
+test("counts and steps through every match in the chat, not just the selected message", async ({
+  page,
+}, testInfo) => {
+  const agent = await seedMockAgentWorkspace({
+    repoPrefix: "chat-find-across-",
+    title: "Chat Find across messages",
+    initialPrompt: ACROSS_PROMPT,
+    featureValues: { mockAssistantResponse: ACROSS_RESPONSE },
+  });
+  try {
+    await agent.client.waitForFinish(agent.agentId, 15_000);
+    await openAgentRoute(page, agent);
+    await expect(page.getByTestId("assistant-message").first()).toBeVisible();
+    // One hit in the prompt and two in the reply: three across the chat.
+    await searchChat(page, "scope-needle");
+    await expect(status(page)).toHaveText("1 of 3");
+    await expectHighlight(page, "scope-needle");
+    await expectHighlightedMessage(page, "user-message");
+    await page.screenshot({ path: testInfo.outputPath("chat-find-across-messages.png") });
+    await expectNextMatch(page, "2 of 3", "scope-needle");
+    await expectHighlightedMessage(page, "assistant-message");
+    await expectNextMatch(page, "3 of 3", "scope-needle");
+    await expectHighlightedMessage(page, "assistant-message");
+    await page.screenshot({ path: testInfo.outputPath("chat-find-last-match.png") });
+    await expectNextMatch(page, "1 of 3", "scope-needle");
+    await expectHighlightedMessage(page, "user-message");
+    await previousMatch(page);
+    await expect(status(page)).toHaveText("3 of 3");
+    await expectHighlight(page, "scope-needle");
+    await expectHighlightedMessage(page, "assistant-message");
+    await closeFind(page);
+  } finally {
+    await agent.cleanup();
+  }
+});
+
 test("rejects invisible source matches and ignores a late reply after closing", async ({
   page,
 }) => {
@@ -264,12 +323,12 @@ test("finds a hit in a message that streamed while the chat was open", async ({
   try {
     await openChatFind(page);
     // The only hit is in the first paragraph, which is no longer the row that grows.
-    await expectFindStatus(page, "alpha-needle", "1 of 1 in message");
+    await expectFindStatus(page, "alpha-needle", "1 of 1");
     await chat.replyFinished();
-    await expectFindStatus(page, "beta-needle", "1 of 1 in message");
+    await expectFindStatus(page, "beta-needle", "1 of 1");
     // One message, two Markdown blocks, one count across both.
-    await expectFindStatus(page, "pair-needle", "1 of 2 in message");
-    await expectNextMatch(page, "2 of 2 in message", "pair-needle");
+    await expectFindStatus(page, "pair-needle", "1 of 2");
+    await expectNextMatch(page, "2 of 2", "pair-needle");
     await closeFind(page);
   } finally {
     await chat.cleanup();
@@ -311,9 +370,9 @@ test("counts every occurrence of a virtualized message and steps between them",
   const chat = await openChatWithVirtualizedTallMessage(page);
   try {
     await openChatFind(page);
-    await expectFindStatus(page, "span-needle", "1 of 2 in message");
+    await expectFindStatus(page, "span-needle", "1 of 12");
     await expectHighlight(page, "span-needle");
-    await expectNextMatch(page, "2 of 2 in message", "span-needle");
+    await expectNextMatch(page, "2 of 12", "span-needle");
     await closeFind(page);
   } finally {
     await chat.cleanup();
diff --git a/packages/app/src/agent-stream/chat-find/index.web.tsx b/packages/app/src/agent-stream/chat-find/index.web.tsx
index 7a36416948..c817b55028 100644
--- a/packages/app/src/agent-stream/chat-find/index.web.tsx
+++ b/packages/app/src/agent-stream/chat-find/index.web.tsx
@@ -126,7 +126,7 @@ export function ChatFind({
   else if (state.phase === "error") status = t("paneFind.failed");
   else if (state.query.trim())
     status = state.count
-      ? t("paneFind.chatPosition", { current: state.occurrence + 1, total: state.count })
+      ? t("paneFind.position", { current: state.occurrence + 1, total: state.count })
       : t("paneFind.noMatches");
   return (
     <div ref={root} tabIndex={-1} style={ROOT_STYLE}>
diff --git a/packages/app/src/agent-stream/chat-find/model.test.ts b/packages/app/src/agent-stream/chat-find/model.test.ts
index d1e784e19f..abc3ade6c6 100644
--- a/packages/app/src/agent-stream/chat-find/model.test.ts
+++ b/packages/app/src/agent-stream/chat-find/model.test.ts
@@ -2,7 +2,7 @@ import { expect, it } from "vitest";
 import { hydrateStreamState, type StreamItem } from "@/types/stream";
 import { ChatFindModel, type ChatFindOperations } from "./model";
 
-function response(locations: Array<{ seq: number; role: "user" | "assistant" }>) {
+function response(locations: Array<{ seq: number; role: "user" | "assistant"; count?: number }>) {
   return {
     agentId: "agent",
     requestId: "request",
@@ -241,3 +241,73 @@ it("can load a search location before the initial chat history has arrived", asy
     model.close();
   }
 });
+
+// The scope of the search is the whole chat, so the position spans every located
+// message: the host's estimate until a message is on screen, the rendered count after.
+it("reports the position across the whole chat and corrects it with rendered counts", async () => {
+  const model = new ChatFindModel({
+    async search() {
+      return response([
+        { seq: 1, role: "assistant", count: 2 },
+        { seq: 2, role: "assistant", count: 3 },
+      ]);
+    },
+    async load() {},
+    async reveal(id, _query, occurrence) {
+      const count = id === "row-1" ? 2 : 1;
+      return { count, occurrence: occurrence < 0 ? count - 1 : occurrence };
+    },
+    clear() {},
+  });
+  try {
+    model.updateHistory("epoch", [message(1), message(2)]);
+    model.open();
+    model.setQuery("target");
+    await expect.poll(() => model.getSnapshot().phase).toBe("ready");
+    expect(model.getSnapshot()).toMatchObject({ selectedItemId: "row-1", occurrence: 0, count: 5 });
+    model.next();
+    await expect.poll(() => model.getSnapshot().occurrence).toBe(1);
+    expect(model.getSnapshot().count).toBe(5);
+    model.next();
+    await expect.poll(() => model.getSnapshot().selectedItemId).toBe("row-2");
+    expect(model.getSnapshot()).toMatchObject({ occurrence: 2, count: 3 });
+    model.previous();
+    await expect.poll(() => model.getSnapshot().selectedItemId).toBe("row-1");
+    expect(model.getSnapshot()).toMatchObject({ occurrence: 1, count: 3 });
+  } finally {
+    model.close();
+  }
+});
+
+// COMPAT(timelineSearchCount): a host that reports no counts is worth one match per
+// located message until a reveal replaces the estimate with the rendered count.
+it("counts one match per message from a host that reports no counts", async () => {
+  const model = new ChatFindModel({
+    async search() {
+      return response([
+        { seq: 1, role: "assistant" },
+        { seq: 2, role: "assistant" },
+      ]);
+    },
+    async load() {},
+    async reveal(id, _query, occurrence) {
+      const count = id === "row-1" ? 2 : 1;
+      return { count, occurrence: occurrence < 0 ? count - 1 : occurrence };
+    },
+    clear() {},
+  });
+  try {
+    model.updateHistory("epoch", [message(1), message(2)]);
+    model.open();
+    model.setQuery("target");
+    await expect.poll(() => model.getSnapshot().phase).toBe("ready");
+    expect(model.getSnapshot()).toMatchObject({ selectedItemId: "row-1", occurrence: 0, count: 3 });
+    model.next();
+    await expect.poll(() => model.getSnapshot().occurrence).toBe(1);
+    model.next();
+    await expect.poll(() => model.getSnapshot().selectedItemId).toBe("row-2");
+    expect(model.getSnapshot()).toMatchObject({ occurrence: 2, count: 3 });
+  } finally {
+    model.close();
+  }
+});
diff --git a/packages/app/src/agent-stream/chat-find/model.ts b/packages/app/src/agent-stream/chat-find/model.ts
index 0cd9f39af7..98acc9840f 100644
--- a/packages/app/src/agent-stream/chat-find/model.ts
+++ b/packages/app/src/agent-stream/chat-find/model.ts
@@ -1,7 +1,15 @@
 import type { AgentTimelineSearchPayload } from "@getpaseo/client/internal/daemon-client";
 import type { StreamItem } from "@/types/stream";
 
-type Location = AgentTimelineSearchPayload["locations"][number];
+/**
+ * A message the host says contains the query. `count` is the host's estimate of its
+ * occurrences until a reveal replaces it with the rendered count, so the whole-chat
+ * position the widget shows is exact for every message that has been on screen. The
+ * wire field is optional; the search boundary fills it in, so the interior trusts it.
+ */
+type Location = Omit<AgentTimelineSearchPayload["locations"][number], "count"> & {
+  count: number;
+};
 interface Target {
   id: string;
   seq: number;
@@ -36,6 +44,7 @@ interface Snapshot {
   query: string;
   phase: "idle" | "searching" | "loading" | "ready" | "error";
   selectedItemId: string | null;
+  /** Position across the whole chat: the search scope, not the selected message. */
   occurrence: number;
   count: number;
   failure: ChatFindFailure | null;
@@ -70,6 +79,7 @@ export class ChatFindModel {
   private locations: Location[] = [];
   private resolved = new Map<Location, Target>();
   private current = -1;
+  private inMessage = { occurrence: 0, count: 0 };
   private abort = new AbortController();
   private timer: ReturnType<typeof setTimeout> | undefined;
   constructor(private operations: ChatFindOperations) {}
@@ -105,6 +115,7 @@ export class ChatFindModel {
     this.resultEpoch = null;
     this.resolved.clear();
     this.current = -1;
+    this.inMessage = { occurrence: 0, count: 0 };
     this.publish({
       query,
       phase: query.trim() ? "searching" : "idle",
@@ -142,7 +153,14 @@ export class ChatFindModel {
         const searchChanged = this.resultEpoch !== null && result.epoch !== this.resultEpoch;
         if (historyChanged || searchChanged) throw new ChatFindFailureError("historyChanged");
         this.resultEpoch = result.epoch;
-        this.locations.push(...result.locations);
+        this.locations.push(
+          ...result.locations.map((location) => ({
+            seq: location.seq,
+            role: location.role,
+            // COMPAT(timelineSearchCount): hosts before v0.9.0 send no count; remove after 2027-09-22.
+            count: location.count ?? 1,
+          })),
+        );
         cursor = result.nextCursor ?? undefined;
       } while (cursor !== undefined);
       await this.navigate(0, 1, signal);
@@ -238,7 +256,7 @@ export class ChatFindModel {
       if (signal.aborted) return;
       if (result.count) {
         this.current = index;
-        this.publish({ phase: "ready", ...result });
+        this.publish({ phase: "ready", ...this.position(location, result) });
         return;
       }
       this.locations.splice(index, 1);
@@ -247,13 +265,24 @@ export class ChatFindModel {
     this.operations.clear();
     this.publish({ phase: "ready", selectedItemId: null, count: 0, occurrence: 0 });
   }
+  private position(location: Location, revealed: { occurrence: number; count: number }) {
+    this.inMessage = revealed;
+    location.count = revealed.count;
+    let before = 0;
+    let total = 0;
+    for (const candidate of this.locations) {
+      if (candidate === location) before = total;
+      total += candidate.count;
+    }
+    return { occurrence: before + revealed.occurrence, count: total };
+  }
   private async move(direction: 1 | -1) {
     if (this.state.phase !== "ready" || !this.state.count) return;
     this.cancel();
     const signal = this.abort.signal;
     try {
-      const occurrence = this.state.occurrence + direction;
-      if (occurrence >= 0 && occurrence < this.state.count && this.state.selectedItemId) {
+      const occurrence = this.inMessage.occurrence + direction;
+      if (occurrence >= 0 && occurrence < this.inMessage.count && this.state.selectedItemId) {
         this.publish({ phase: "loading" });
         const result = await tagged(
           "reveal",
@@ -261,7 +290,7 @@ export class ChatFindModel {
         );
         if (signal.aborted) return;
         if (result.count) {
-          this.publish({ phase: "ready", ...result });
+          this.publish({ phase: "ready", ...this.position(this.locations[this.current]!, result) });
           return;
         }
       }
diff --git a/packages/app/src/i18n/resources/ar.ts b/packages/app/src/i18n/resources/ar.ts
index c7e6199af5..2f4925572d 100644
--- a/packages/app/src/i18n/resources/ar.ts
+++ b/packages/app/src/i18n/resources/ar.ts
@@ -10,7 +10,6 @@ export const ar: TranslationResources = {
     loading: "جارٍ التحميل…",
     failed: "فشل",
     retry: "إعادة المحاولة",
-    chatPosition: "{{current}} من {{total}} في الرسالة",
 
     title: "بحث",
     placeholder: "بحث في اللوحة",
diff --git a/packages/app/src/i18n/resources/en.ts b/packages/app/src/i18n/resources/en.ts
index 9ae394bc29..671aeeaf32 100644
--- a/packages/app/src/i18n/resources/en.ts
+++ b/packages/app/src/i18n/resources/en.ts
@@ -7,7 +7,6 @@ export const en = {
     loading: "Loading…",
     failed: "Failed",
     retry: "Retry",
-    chatPosition: "{{current}} of {{total}} in message",
     title: "Find",
     placeholder: "Find in pane",
     close: "Close Find",
diff --git a/packages/app/src/i18n/resources/es.ts b/packages/app/src/i18n/resources/es.ts
index 7c3a9a15ad..ccbc3dcc98 100644
--- a/packages/app/src/i18n/resources/es.ts
+++ b/packages/app/src/i18n/resources/es.ts
@@ -11,7 +11,6 @@ export const es: TranslationResources = {
     loading: "Cargando…",
     failed: "Error",
     retry: "Reintentar",
-    chatPosition: "{{current}} de {{total}} en el mensaje",
 
     title: "Buscar",
     placeholder: "Buscar en el panel",
diff --git a/packages/app/src/i18n/resources/fr.ts b/packages/app/src/i18n/resources/fr.ts
index 310230d930..261565b863 100644
--- a/packages/app/src/i18n/resources/fr.ts
+++ b/packages/app/src/i18n/resources/fr.ts
@@ -11,7 +11,6 @@ export const fr: TranslationResources = {
     loading: "Chargement…",
     failed: "Échec",
     retry: "Réessayer",
-    chatPosition: "{{current}} sur {{total}} dans le message",
 
     title: "Rechercher",
     placeholder: "Rechercher dans le panneau",
diff --git a/packages/app/src/i18n/resources/ja.ts b/packages/app/src/i18n/resources/ja.ts
index 605ca7454d..db698b6e85 100644
--- a/packages/app/src/i18n/resources/ja.ts
+++ b/packages/app/src/i18n/resources/ja.ts
@@ -11,7 +11,6 @@ export const ja: TranslationResources = {
     loading: "読み込み中…",
     failed: "失敗",
     retry: "再試行",
-    chatPosition: "メッセージ内 {{current}} / {{total}}",
 
     title: "検索",
     placeholder: "ペイン内を検索",
diff --git a/packages/app/src/i18n/resources/ko.ts b/packages/app/src/i18n/resources/ko.ts
index 6e0a7897ba..44902af668 100644
--- a/packages/app/src/i18n/resources/ko.ts
+++ b/packages/app/src/i18n/resources/ko.ts
@@ -10,7 +10,6 @@ export const ko: TranslationResources = {
     loading: "불러오는 중…",
     failed: "실패",
     retry: "다시 시도",
-    chatPosition: "메시지 내 {{current}} / {{total}}",
 
     title: "찾기",
     placeholder: "패널에서 찾기",
diff --git a/packages/app/src/i18n/resources/pt-BR.ts b/packages/app/src/i18n/resources/pt-BR.ts
index 9c9ec29bf2..ff76c70b43 100644
--- a/packages/app/src/i18n/resources/pt-BR.ts
+++ b/packages/app/src/i18n/resources/pt-BR.ts
@@ -11,7 +11,6 @@ export const ptBR: TranslationResources = {
     loading: "Carregando…",
     failed: "Falhou",
     retry: "Tentar novamente",
-    chatPosition: "{{current}} de {{total}} na mensagem",
 
     title: "Buscar",
     placeholder: "Buscar no painel",
diff --git a/packages/app/src/i18n/resources/ru.ts b/packages/app/src/i18n/resources/ru.ts
index 6a1b9e4a9b..59eafaf092 100644
--- a/packages/app/src/i18n/resources/ru.ts
+++ b/packages/app/src/i18n/resources/ru.ts
@@ -11,7 +11,6 @@ export const ru: TranslationResources = {
     loading: "Загрузка…",
     failed: "Ошибка",
     retry: "Повторить",
-    chatPosition: "{{current}} из {{total}} в сообщении",
 
     title: "Найти",
     placeholder: "Найти в панели",
diff --git a/packages/app/src/i18n/resources/zh-CN.ts b/packages/app/src/i18n/resources/zh-CN.ts
index 467bf3cdeb..b2513843cb 100644
--- a/packages/app/src/i18n/resources/zh-CN.ts
+++ b/packages/app/src/i18n/resources/zh-CN.ts
@@ -10,7 +10,6 @@ export const zhCN: TranslationResources = {
     loading: "加载中…",
     failed: "失败",
     retry: "重试",
-    chatPosition: "消息内第 {{current}} 项，共 {{total}} 项",
 
     title: "查找",
     placeholder: "在窗格中查找",
diff --git a/packages/protocol/src/messages.ts b/packages/protocol/src/messages.ts
index f174a2dfe0..1c6882223a 100644
--- a/packages/protocol/src/messages.ts
+++ b/packages/protocol/src/messages.ts
@@ -4608,7 +4608,13 @@ export const AgentTimelineSearchResponseMessageSchema = z.object({
     agentId: z.string(),
     epoch: z.string(),
     locations: z.array(
-      z.object({ seq: z.number().int().nonnegative(), role: z.enum(["user", "assistant"]) }),
+      z.object({
+        seq: z.number().int().nonnegative(),
+        role: z.enum(["user", "assistant"]),
+        // Estimated occurrences in the message; the client verifies against rendered text.
+        // COMPAT(timelineSearchCount): added in v0.9.0, remove optional after 2027-09-22.
+        count: z.number().int().positive().optional(),
+      }),
     ),
     nextCursor: z.number().int().nonnegative().nullable(),
     error: z.string().nullable(),
diff --git a/packages/server/src/server/agent/chat-search/index.test.ts b/packages/server/src/server/agent/chat-search/index.test.ts
index 2a9a9bf0e2..41054d167c 100644
--- a/packages/server/src/server/agent/chat-search/index.test.ts
+++ b/packages/server/src/server/agent/chat-search/index.test.ts
@@ -19,7 +19,10 @@ it("returns source locations for formatted assistant text and literal user text"
     ]),
     query: "hello world",
   });
-  expect(result).toEqual({ locations: [{ seq: 2, role: "assistant" }], nextCursor: null });
+  expect(result).toEqual({
+    locations: [{ seq: 2, role: "assistant", count: 2 }],
+    nextCursor: null,
+  });
 });
 
 it("finds code and literal punctuation without searching tools, reasoning, or task state", async () => {
@@ -34,8 +37,8 @@ it("finds code and literal punctuation without searching tools, reasoning, or ta
     query: "a.b",
   });
   expect(result.locations).toEqual([
-    { seq: 1, role: "assistant" },
-    { seq: 5, role: "user" },
+    { seq: 1, role: "assistant", count: 1 },
+    { seq: 5, role: "user", count: 1 },
   ]);
 });
 
@@ -49,8 +52,8 @@ it("bounds results and resumes without losing locations", async () => {
   const second = await searchTimeline({ rows: source, query: "target", cursor: first.nextCursor! });
   expect(second).toEqual({
     locations: [
-      { seq: 201, role: "user" },
-      { seq: 202, role: "user" },
+      { seq: 201, role: "user", count: 1 },
+      { seq: 202, role: "user", count: 1 },
     ],
     nextCursor: null,
   });
@@ -59,9 +62,27 @@ it("bounds results and resumes without losing locations", async () => {
 it("finds ordinary Markdown entities and line breaks without requiring identical parsers", async () => {
   const source = rows([{ type: "assistant_message", text: "hello &amp; **world**\nnext line" }]);
   expect((await searchTimeline({ rows: source, query: "hello & world" })).locations).toEqual([
-    { seq: 1, role: "assistant" },
+    { seq: 1, role: "assistant", count: 1 },
   ]);
   expect((await searchTimeline({ rows: source, query: "world next" })).locations).toEqual([
-    { seq: 1, role: "assistant" },
+    { seq: 1, role: "assistant", count: 1 },
   ]);
 });
+
+it("counts occurrences per rendered block rather than across block boundaries", async () => {
+  const source = rows([
+    { type: "assistant_message", text: "target one\n\ntarget two\n\n- target three\n- end target" },
+    { type: "user_message", text: "TARGET target" },
+  ]);
+  expect((await searchTimeline({ rows: source, query: "target" })).locations).toEqual([
+    { seq: 1, role: "assistant", count: 4 },
+    { seq: 2, role: "user", count: 2 },
+  ]);
+  expect((await searchTimeline({ rows: source, query: "end target" })).locations).toEqual([
+    { seq: 1, role: "assistant", count: 1 },
+  ]);
+  expect((await searchTimeline({ rows: source, query: "two target" })).locations).toEqual([]);
+  // Rendered text never runs from the end of one block into the start of the next, so
+  // neither does a match, however contiguous the Markdown source looks.
+  expect((await searchTimeline({ rows: source, query: "one target" })).locations).toEqual([]);
+});
diff --git a/packages/server/src/server/agent/chat-search/index.ts b/packages/server/src/server/agent/chat-search/index.ts
index eee1cb57f5..70ada71b57 100644
--- a/packages/server/src/server/agent/chat-search/index.ts
+++ b/packages/server/src/server/agent/chat-search/index.ts
@@ -8,6 +8,7 @@ const PAGE_SIZE = 200;
 interface SearchLocation {
   seq: number;
   role: "user" | "assistant";
+  count: number;
 }
 interface SearchInput {
   rows: readonly AgentTimelineRow[];
@@ -15,8 +16,13 @@ interface SearchInput {
   cursor?: number;
 }
 
-// Discovery is deliberately approximate. Only the client can verify displayed text.
-function searchableMarkdown(text: string): string {
+// Discovery is deliberately approximate. Only the client can verify displayed text, so
+// `count` estimates rendered occurrences and the client replaces it with the rendered
+// count once the message is on screen. Blocks are counted separately, and the Markdown
+// source is never searched whole, because a match the client cannot highlight — across
+// a block boundary, or on syntax the reader never sees — still inflates the total until
+// navigation reaches that message and drops it.
+function searchableBlocks(text: string): string[] {
   return markdown
     .parse(text, {})
     .map((token) => {
@@ -32,28 +38,44 @@ function searchableMarkdown(text: string): string {
       if (token.type === "fence" || token.type === "code_block") return token.content;
       return "";
     })
-    .filter(Boolean)
-    .join("\n");
+    .filter(Boolean);
+}
+
+function searchPattern(query: string): RegExp {
+  const source = query
+    .trim()
+    .split(/\s+/)
+    .map((part) => part.replace(/[.*+?^${}()|[\]\\]/g, "\\$&"))
+    .join("\\s+");
+  return new RegExp(source, "giu");
+}
+
+function countMatches(text: string, pattern: RegExp): number {
+  let count = 0;
+  for (const _ of text.matchAll(pattern)) count += 1;
+  return count;
 }
 
 export async function searchTimeline({ rows, query, cursor = 0 }: SearchInput) {
   const locations: SearchLocation[] = [];
   if (!query.trim()) return { locations, nextCursor: null };
-  const needle = normalizeSearchText(query);
+  const pattern = searchPattern(query);
   let lastYield = performance.now();
   for (const entry of projectTimelineRows({ rows, mode: "projected" })) {
     if (entry.seqEnd <= cursor) continue;
     const item = entry.item;
     if (item.type !== "user_message" && item.type !== "assistant_message") continue;
     const raw = item.text.replace(/\r/g, "");
-    const text = item.type === "assistant_message" ? searchableMarkdown(raw) : raw;
-    if (normalizeSearchText(raw).includes(needle) || normalizeSearchText(text).includes(needle)) {
+    const blocks = item.type === "assistant_message" ? searchableBlocks(raw) : [raw];
+    const count = blocks.reduce((sum, block) => sum + countMatches(block, pattern), 0);
+    if (count) {
       if (locations.length === PAGE_SIZE) {
         return { locations, nextCursor: locations[PAGE_SIZE - 1]!.seq };
       }
       locations.push({
         seq: entry.seqEnd,
         role: item.type === "user_message" ? "user" : "assistant",
+        count,
       });
     }
     if (performance.now() - lastYield >= 8) {
@@ -63,7 +85,3 @@ export async function searchTimeline({ rows, query, cursor = 0 }: SearchInput) {
   }
   return { locations, nextCursor: null };
 }
-
-function normalizeSearchText(text: string): string {
-  return text.replace(/\s+/g, " ").trim().toLowerCase();
-}