Improve session transcript search

apps/app/src/react-app/domains/session/chat/session-page.tsx

@@ -109,6 +109,7 @@ export type SessionPageSidebarProps = {
   onPrefetchSession?: (workspaceId: string, sessionId: string) => void;
   onCreateTaskInWorkspace: (workspaceId: string) => void;
   onCreateTaskWithPrompt?: (workspaceId: string, prompt: string) => void;
+  onOpenSessionSearch?: () => void;
   onOpenRenameWorkspace: (workspaceId: string) => void;
   onShareWorkspace: (workspaceId: string) => void;
   onRevealWorkspace: (workspaceId: string) => void;
@@ -831,6 +832,7 @@ export function SessionPage(props: SessionPageProps) {
           onOpenSession={openSessionTab}
           onPrefetchSession={props.sidebar.onPrefetchSession}
           onCreateTaskInWorkspace={props.sidebar.onCreateTaskInWorkspace}
+          onOpenSessionSearch={props.sidebar.onOpenSessionSearch}
           onOpenRenameSession={props.onRenameSession ? openRenameModal : undefined}
           onOpenDeleteSession={props.onDeleteSession ? (sessionId) => {
             setSessionActionId(sessionId);

apps/app/src/react-app/domains/session/search/session-search.ts

@@ -32,11 +32,32 @@ export type SessionSearchProgress = {
 type CacheEntry = {
   updatedAt: number;
   /** One entry per message that contains searchable text. */
-  texts: Array<{ role: "user" | "assistant"; text: string; lower: string }>;
+  texts: Array<{ role: "user" | "assistant"; text: string; words: WordRange[] }>;
   /** Set when the transcript fetch failed; retried after a short cool-down. */
   failedAt?: number;
 };
 
+type QueryToken = {
+  value: string;
+};
+
+type WordRange = {
+  value: string;
+  start: number;
+  end: number;
+};
+
+type TokenRange = {
+  start: number;
+  end: number;
+  score: number;
+};
+
+type TokenizedMatch = {
+  ranges: TokenRange[];
+  score: number;
+};
+
 export type SessionMessageFetcher = (
   workspaceId: string,
   sessionId: string,
@@ -46,18 +67,114 @@ const SNIPPET_BEFORE = 36;
 const SNIPPET_AFTER = 72;
 const DEFAULT_CONCURRENCY = 6;
 const FAILURE_RETRY_MS = 30_000;
+const MIN_TOKEN_LENGTH = 2;
+const WORD_PATTERN = /[\p{L}\p{N}_./-]+/gu;
+const STOP_WORDS = new Set([
+  "a",
+  "an",
+  "and",
+  "are",
+  "for",
+  "in",
+  "is",
+  "of",
+  "on",
+  "or",
+  "the",
+  "to",
+  "with",
+]);
 
 function collapseWhitespace(value: string): string {
   return value.replace(/\s+/g, " ");
 }
 
-/** Build a compact snippet centered on the first occurrence of the query. */
-export function buildSnippet(text: string, index: number, length: number): SessionSearchSnippet {
-  const start = Math.max(0, index - SNIPPET_BEFORE);
-  const end = Math.min(text.length, index + length + SNIPPET_AFTER);
-  const before = `${start > 0 ? "…" : ""}${collapseWhitespace(text.slice(start, index)).trimStart()}`;
-  const after = `${collapseWhitespace(text.slice(index + length, end)).trimEnd()}${end < text.length ? "…" : ""}`;
-  return { before, match: text.slice(index, index + length), after };
+function tokenizeQuery(query: string): QueryToken[] {
+  const seen = new Set<string>();
+  const tokens: QueryToken[] = [];
+  for (const match of query.toLowerCase().matchAll(WORD_PATTERN)) {
+    const value = match[0];
+    if (value.length < MIN_TOKEN_LENGTH || STOP_WORDS.has(value) || seen.has(value)) continue;
+    seen.add(value);
+    tokens.push({ value });
+  }
+  return tokens;
+}
+
+function wordRanges(lower: string): WordRange[] {
+  const ranges: WordRange[] = [];
+  for (const match of lower.matchAll(WORD_PATTERN)) {
+    ranges.push({
+      value: match[0],
+      start: match.index,
+      end: match.index + match[0].length,
+    });
+  }
+  return ranges;
+}
+
+function scoreWordForToken(word: WordRange, token: QueryToken): TokenRange | null {
+  if (word.value === token.value) {
+    return { start: word.start, end: word.end, score: 120 };
+  }
+  if (word.value.startsWith(token.value)) {
+    return { start: word.start, end: word.end, score: 95 };
+  }
+
+  const index = word.value.indexOf(token.value);
+  if (index >= 0) {
+    return {
+      start: word.start + index,
+      end: word.start + index + token.value.length,
+      score: 75,
+    };
+  }
+
+  return null;
+}
+
+function findBestTokenRange(words: WordRange[], token: QueryToken): TokenRange | null {
+  let best: TokenRange | null = null;
+  for (const word of words) {
+    const range = scoreWordForToken(word, token);
+    if (!range) continue;
+    if (!best || range.score > best.score) {
+      best = range;
+    }
+  }
+  return best;
+}
+
+function matchTokenizedQuery(words: WordRange[], tokens: QueryToken[]): TokenizedMatch | null {
+  if (tokens.length === 0) return null;
+
+  const ranges: TokenRange[] = [];
+  for (const token of tokens) {
+    const range = findBestTokenRange(words, token);
+    if (!range) return null;
+    ranges.push(range);
+  }
+
+  const sorted = [...ranges].sort((a, b) => a.start - b.start);
+  const span = sorted[sorted.length - 1].end - sorted[0].start;
+  const proximityBonus = Math.max(0, 120 - span);
+  const score = ranges.reduce((sum, range) => sum + range.score, 0) + proximityBonus;
+
+  return { ranges: sorted, score };
+}
+
+function buildTokenSnippet(text: string, ranges: TokenRange[]): SessionSearchSnippet {
+  const highlight = ranges.reduce((best, range) => {
+    if (range.score !== best.score) return range.score > best.score ? range : best;
+    return range.start < best.start ? range : best;
+  }, ranges[0]);
+  const start = Math.max(0, highlight.start - SNIPPET_BEFORE);
+  const end = Math.min(text.length, highlight.end + SNIPPET_AFTER);
+  return {
+    before: `${start > 0 ? "…" : ""}${collapseWhitespace(text.slice(start, highlight.start)).trimStart()}`,
+    match: collapseWhitespace(text.slice(highlight.start, highlight.end)),
+    after: `${collapseWhitespace(text.slice(highlight.end, end)).trimEnd()}${end < text.length ? "…" : ""}`,
+  };
 }
 
 function toCacheEntry(updatedAt: number, messages: OpenworkSessionMessage[]): CacheEntry {
@@ -70,7 +187,8 @@ function toCacheEntry(updatedAt: number, messages: OpenworkSessionMessage[]): Ca
       if (part.synthetic || part.ignored) continue;
       const text = part.text.trim();
       if (!text) continue;
-      texts.push({ role, text, lower: text.toLowerCase() });
+      const lower = text.toLowerCase();
+      texts.push({ role, text, words: wordRanges(lower) });
     }
   }
   return { updatedAt, texts };
@@ -79,23 +197,24 @@ function toCacheEntry(updatedAt: number, messages: OpenworkSessionMessage[]): Ca
 function matchEntry(
   session: SearchableSession,
   entry: CacheEntry,
-  queryLower: string,
+  queryTokens: QueryToken[],
 ): SessionSearchMatch | null {
-  // Prefer the user's own prompts: they are usually what people remember typing.
-  let fallback: SessionSearchMatch | null = null;
+  let best: { match: SessionSearchMatch; score: number } | null = null;
   for (const item of entry.texts) {
-    const index = item.lower.indexOf(queryLower);
-    if (index < 0) continue;
+    const tokenMatch = matchTokenizedQuery(item.words, queryTokens);
+    if (!tokenMatch) continue;
+    const score = tokenMatch.score + (item.role === "user" ? 50 : 0);
     const match: SessionSearchMatch = {
       session,
       kind: "message",
       role: item.role,
-      snippet: buildSnippet(item.text, index, queryLower.length),
+      snippet: buildTokenSnippet(item.text, tokenMatch.ranges),
     };
-    if (item.role === "user") return match;
-    if (!fallback) fallback = match;
+    if (!best || score > best.score) {
+      best = { match, score };
+    }
   }
-  return fallback;
+  return best?.match ?? null;
 }
 
 export type SessionSearchRun = {
@@ -138,9 +257,7 @@ export function createSessionSearcher(fetchMessages: SessionMessageFetcher): Ses
       const messages = await fetchMessages(session.workspaceId, session.sessionId);
       entry = toCacheEntry(session.updatedAt, messages);
     } catch {
-      // Unreachable session (stale workspace, server hiccup): record an empty
-      // entry with a cool-down so one bad session cannot stall every later
-      // keystroke, but still gets retried once the cool-down expires.
+      // Keep one stale workspace or server hiccup from blocking every keystroke.
       entry = { ...toCacheEntry(session.updatedAt, []), failedAt: Date.now() };
     }
     cache.set(session.sessionId, entry);
@@ -149,7 +266,7 @@ export function createSessionSearcher(fetchMessages: SessionMessageFetcher): Ses
 
   return {
     search({ query, sessions, onMatch, onProgress, concurrency = DEFAULT_CONCURRENCY }) {
-      const queryLower = query.trim().toLowerCase();
+      const queryTokens = tokenizeQuery(query);
       let cancelled = false;
 
       // Scan newest sessions first so the most relevant hits stream in early.
@@ -169,14 +286,14 @@ export function createSessionSearcher(fetchMessages: SessionMessageFetcher): Ses
           const entry = await getEntry(session);
           if (cancelled) return;
           scanned += 1;
-          const match = matchEntry(session, entry, queryLower);
+          const match = matchEntry(session, entry, queryTokens);
           if (match) onMatch(match);
           report();
         }
       };
 
       const done = (async () => {
-        if (!queryLower) {
+        if (queryTokens.length === 0) {
           scanned = total;
           report();
           return;

apps/app/src/react-app/domains/session/sidebar/app-sidebar-provider.tsx

@@ -19,6 +19,7 @@ export type SidebarContextValue = {
   onOpenDeleteSession?: (sessionId: string) => void;
   onArchiveSession?: (sessionId: string, archived: boolean) => void;
   onOpenCreateGroupModal?: (workspaceId: string) => void;
+  onOpenSessionSearch?: () => void;
   onOpenRenameWorkspace: (workspaceId: string) => void;
   onShareWorkspace: (workspaceId: string) => void;
   onRevealWorkspace: (workspaceId: string) => void;

apps/app/src/react-app/domains/session/sidebar/app-sidebar.tsx

@@ -12,6 +12,7 @@ import {
   Pin,
   PinOff,
   Plus,
+  Search,
   Share2,
   Trash2,
   RefreshCw,
@@ -33,6 +34,7 @@ import {
   isRemoteConnectionErrorMessage,
   getWorkspaceTaskLoadErrorDisplay,
   isRemoteConnectionWorkspace,
+  isMacPlatform,
   isWindowsPlatform,
 } from "../../../../app/utils";
 import { t } from "../../../../i18n";
@@ -573,6 +575,7 @@ export type AppSidebarProps = {
   onOpenDeleteSession?: (sessionId: string) => void;
   onArchiveSession?: (sessionId: string, archived: boolean) => void;
   onOpenCreateGroupModal?: (workspaceId: string) => void;
+  onOpenSessionSearch?: () => void;
   onOpenRenameWorkspace: (workspaceId: string) => void;
   onShareWorkspace: (workspaceId: string) => void;
   onRevealWorkspace: (workspaceId: string) => void;
@@ -663,6 +666,7 @@ export function AppSidebar(props: AppSidebarProps) {
       [workspaceId]: Math.min((current[workspaceId] ?? MAX_SESSIONS_PREVIEW) + MAX_SESSIONS_PREVIEW, totalRoots),
     }));
   };
+  const sessionSearchShortcut = isMacPlatform() ? "Cmd+Shift+F" : "Ctrl+Shift+F";
 
   React.useEffect(() => {
     const workspaceId = props.selectedWorkspaceId.trim();
@@ -709,6 +713,7 @@ export function AppSidebar(props: AppSidebarProps) {
     onOpenDeleteSession: props.onOpenDeleteSession,
     onArchiveSession: props.onArchiveSession,
     onOpenCreateGroupModal: props.onOpenCreateGroupModal,
+    onOpenSessionSearch: props.onOpenSessionSearch,
     onOpenRenameWorkspace: props.onOpenRenameWorkspace,
     onShareWorkspace: props.onShareWorkspace,
     onRevealWorkspace: props.onRevealWorkspace,
@@ -760,6 +765,18 @@ export function AppSidebar(props: AppSidebarProps) {
 
         <SidebarFooter>
           <SidebarMenu>
+            {props.onOpenSessionSearch ? (
+              <SidebarMenuItem>
+                <SidebarMenuButton
+                  onClick={props.onOpenSessionSearch}
+                  aria-label={`${t("session.cmd_sessions_title")} (${sessionSearchShortcut})`}
+                  title={`${t("session.cmd_sessions_title")} (${sessionSearchShortcut})`}
+                >
+                  <Search className="size-4" />
+                  {t("session.cmd_sessions_title")}
+                </SidebarMenuButton>
+              </SidebarMenuItem>
+            ) : null}
             <SidebarMenuItem>
               <SidebarMenuButton onClick={props.onOpenCreateWorkspace}>
                 <Plus className="size-4" />

apps/app/src/react-app/shell/session-route.tsx

@@ -1671,6 +1671,7 @@ export function SessionRoute() {
         onCreateTaskInWorkspace: (workspaceId) => {
           void handleCreateTaskInWorkspace(workspaceId);
         },
+        onOpenSessionSearch: () => setSessionSearchOpen(true),
         onCreateTaskWithPrompt: (workspaceId, prompt) => {
           void (async () => {
             const workspace = workspaces.find((item) => item.id === workspaceId);