From dd6cd1ea7b65b5747acd22debaa30f6ebf16353f Mon Sep 17 00:00:00 2001
From: James Magahern <james@magahern.com>
Date: Wed, 7 Oct 2026 22:05:49 -0700
Subject: [PATCH] Add indexed history search across iOS and web

---
 docs/api/rest.md                              |  11 +
 .../Sybil/Sources/Sybil/SybilAPIClient.swift  |  22 +-
 .../Sources/Sybil/SybilAPIClienting.swift     |   1 +
 .../Sybil/Sources/Sybil/SybilModels.swift     |   8 +
 .../Sources/Sybil/SybilPhoneShellView.swift   |   8 +
 .../Sources/Sybil/SybilSidebarView.swift      | 111 ++++++++++-
 .../Sybil/Sources/Sybil/SybilViewModel.swift  | 122 +++++++++++-
 .../Sybil/Tests/SybilTests/SybilTests.swift   | 181 +++++++++++++++++
 ios/README.md                                 |   8 +
 .../migration.sql                             |  70 +++++++
 server/prisma/schema.prisma                   |   1 +
 server/src/routes.ts                          |  32 +++
 server/src/workspace-search.ts                |  74 +++++++
 server/tests/chat-forks.test.ts               |   3 +-
 server/tests/workspace-search.test.ts         | 188 ++++++++++++++++++
 web/README.md                                 |   7 +
 web/src/App.tsx                               | 132 +++++++++---
 .../components/search/search-match-label.tsx  |  96 +++++++++
 web/src/hooks/use-workspace-search.ts         |  30 +++
 web/src/lib/api.ts                            |   8 +-
 web/src/lib/sidebar-selection.ts              |  10 +
 web/src/lib/workspace-search.ts               |  24 +++
 web/tests/workspace-search.test.mjs           |  80 ++++++++
 23 files changed, 1174 insertions(+), 53 deletions(-)
 create mode 100644 server/prisma/migrations/20261007000000_add_workspace_full_text_search/migration.sql
 create mode 100644 server/src/workspace-search.ts
 create mode 100644 server/tests/workspace-search.test.ts
 create mode 100644 web/src/components/search/search-match-label.tsx
 create mode 100644 web/src/hooks/use-workspace-search.ts
 create mode 100644 web/src/lib/workspace-search.ts
 create mode 100644 web/tests/workspace-search.test.mjs

diff --git a/docs/api/rest.md b/docs/api/rest.md
index 58d1955..256d201 100644
--- a/docs/api/rest.md
+++ b/docs/api/rest.md
@@ -81,6 +81,8 @@ Behavior notes:
 
 ### `GET /v1/workspace-items`
 - Response: `{ "items": WorkspaceItem[] }`
+- Optional query: `q` (trimmed string, up to 200 characters). Omit or leave blank for the recent-items list.
+- With nonblank `q`, response: `{ "items": WorkspaceItem[], "hasMore": boolean }`; each item also has `searchSnippet: string | null` (plain text, no HTML).
 - `WorkspaceItem` is a discriminated union sorted by `updatedAt` descending:
 ```json
 {
@@ -123,6 +125,15 @@ Behavior notes:
 - Root chats have `parentChatId: null`. Every fork points directly to its single root chat, including a fork created from another fork, so clients can group rows without traversing a fork chain.
 - `starred`/`starredAt` are backed by membership in a reserved `Project` with id `starred`; future project folders can reuse the same project item model.
 
+History search (`q`) notes:
+- Searches all saved history, including items outside the recent-items window. Chats match their title or the text of a user/assistant message; saved web searches match their title, query, or generated answer. System prompts, tool logs, attachments, and raw web-result payloads are excluded.
+- Case- and diacritic-insensitive Unicode word-prefix matching: `plan` matches `planning`. All query words must match within the title, a single message, or one saved web search (across its indexed fields). Punctuation separates words; quotes, `*`, and operators have no special query syntax. Punctuation-only queries return no matches. This is word-prefix search, not arbitrary substring matching.
+- Returns at most 100 distinct matching items, newest `updatedAt` first, with ties ordered by `type` then `id`. `hasMore` indicates additional matches; refine `q` to narrow them. Unmatched fork roots are not added in search mode. Selecting a fork result opens that fork directly. Search-mode fork results carry their root's `starred`/`starredAt`; clients should star/unstar the `parentChatId`, as in the grouped sidebar.
+- `searchSnippet` is a bounded excerpt from a matching message or saved web search; title-only chat matches have `null`. Clients should render it as plain text.
+- The web and iOS sidebar search fields use this endpoint across saved history. Both display matching excerpts; web title-only chat results display “Title match”.
+- Invalid/non-string queries or queries exceeding 200 characters return `400`. Authentication is unchanged.
+- SQLite FTS5 external-content indexes and prefix indexes serve these queries without scanning or transferring every transcript. The migration backfills existing content; transactional triggers maintain the indexes on inserts, updates, deletes, and cascades. Recent chat listing also has an `updatedAt` index.
+
 ## Chats
 
 ### `GET /v1/chats`
diff --git a/ios/Packages/Sybil/Sources/Sybil/SybilAPIClient.swift b/ios/Packages/Sybil/Sources/Sybil/SybilAPIClient.swift
index f483b59..04d89f3 100644
--- a/ios/Packages/Sybil/Sources/Sybil/SybilAPIClient.swift
+++ b/ios/Packages/Sybil/Sources/Sybil/SybilAPIClient.swift
@@ -49,6 +49,15 @@ actor SybilAPIClient: SybilAPIClienting {
         return response.items
     }
 
+    func searchWorkspaceItems(query: String) async throws -> WorkspaceSearchResponse {
+        try await request(
+            "/v1/workspace-items",
+            method: "GET",
+            queryItems: [URLQueryItem(name: "q", value: query)],
+            responseType: WorkspaceSearchResponse.self
+        )
+    }
+
     func listChats() async throws -> [ChatSummary] {
         let response = try await request("/v1/chats", method: "GET", responseType: ChatListResponse.self)
         return response.chats
@@ -290,9 +299,10 @@ actor SybilAPIClient: SybilAPIClienting {
         _ path: String,
         method: String,
         body: AnyEncodable? = nil,
+        queryItems: [URLQueryItem] = [],
         responseType: Response.Type
     ) async throws -> Response {
-        let request = try makeRequest(path: path, method: method, body: body, acceptsSSE: false)
+        let request = try makeRequest(path: path, method: method, body: body, acceptsSSE: false, queryItems: queryItems)
 
         SybilLog.debug(
             SybilLog.network,
@@ -344,9 +354,10 @@ actor SybilAPIClient: SybilAPIClienting {
         path: String,
         method: String,
         body: AnyEncodable?,
-        acceptsSSE: Bool
+        acceptsSSE: Bool,
+        queryItems: [URLQueryItem] = []
     ) throws -> URLRequest {
-        let url = try buildURL(path: path)
+        let url = try buildURL(path: path, queryItems: queryItems)
         var request = URLRequest(url: url)
         request.httpMethod = method
         request.timeoutInterval = 120
@@ -369,7 +380,7 @@ actor SybilAPIClient: SybilAPIClienting {
         return request
     }
 
-    private func buildURL(path: String) throws -> URL {
+    private func buildURL(path: String, queryItems: [URLQueryItem]) throws -> URL {
         guard var components = URLComponents(url: configuration.baseURL, resolvingAgainstBaseURL: false) else {
             throw APIError.invalidBaseURL
         }
@@ -380,6 +391,9 @@ actor SybilAPIClient: SybilAPIClienting {
             basePath.removeLast()
         }
         components.path = "\(basePath)/\(trimmedPath)"
+        if !queryItems.isEmpty {
+            components.queryItems = (components.queryItems ?? []) + queryItems
+        }
 
         guard let url = components.url else {
             throw APIError.invalidBaseURL
diff --git a/ios/Packages/Sybil/Sources/Sybil/SybilAPIClienting.swift b/ios/Packages/Sybil/Sources/Sybil/SybilAPIClienting.swift
index cbb48d0..18bd213 100644
--- a/ios/Packages/Sybil/Sources/Sybil/SybilAPIClienting.swift
+++ b/ios/Packages/Sybil/Sources/Sybil/SybilAPIClienting.swift
@@ -3,6 +3,7 @@ import Foundation
 protocol SybilAPIClienting: Sendable {
     func verifySession() async throws -> AuthSession
     func listWorkspaceItems() async throws -> [WorkspaceItem]
+    func searchWorkspaceItems(query: String) async throws -> WorkspaceSearchResponse
     func listChats() async throws -> [ChatSummary]
     func createChat(
         title: String?,
diff --git a/ios/Packages/Sybil/Sources/Sybil/SybilModels.swift b/ios/Packages/Sybil/Sources/Sybil/SybilModels.swift
index 7bcdc31..e8a3939 100644
--- a/ios/Packages/Sybil/Sources/Sybil/SybilModels.swift
+++ b/ios/Packages/Sybil/Sources/Sybil/SybilModels.swift
@@ -219,6 +219,7 @@ public struct WorkspaceItem: Codable, Identifiable, Hashable, Sendable {
     public var id: String
     public var title: String?
     public var query: String?
+    public var searchSnippet: String? = nil
     public var parentChatId: String? = nil
     public var titleGenerationPending = false
     public var createdAt: Date
@@ -302,6 +303,7 @@ extension WorkspaceItem {
         case id
         case title
         case query
+        case searchSnippet
         case parentChatId
         case titleGenerationPending
         case createdAt
@@ -320,6 +322,7 @@ extension WorkspaceItem {
         id = try container.decode(String.self, forKey: .id)
         title = try container.decodeIfPresent(String.self, forKey: .title)
         query = try container.decodeIfPresent(String.self, forKey: .query)
+        searchSnippet = try container.decodeIfPresent(String.self, forKey: .searchSnippet)
         parentChatId = try container.decodeIfPresent(String.self, forKey: .parentChatId)
         titleGenerationPending = try container.decodeIfPresent(Bool.self, forKey: .titleGenerationPending) ?? false
         createdAt = try container.decode(Date.self, forKey: .createdAt)
@@ -730,6 +733,11 @@ struct SearchListResponse: Codable {
     var searches: [SearchSummary]
 }
 
+struct WorkspaceSearchResponse: Codable, Sendable {
+    var items: [WorkspaceItem]
+    var hasMore: Bool
+}
+
 struct WorkspaceListResponse: Codable {
     var items: [WorkspaceItem]
 }
diff --git a/ios/Packages/Sybil/Sources/Sybil/SybilPhoneShellView.swift b/ios/Packages/Sybil/Sources/Sybil/SybilPhoneShellView.swift
index 58b8961..bfdc211 100644
--- a/ios/Packages/Sybil/Sources/Sybil/SybilPhoneShellView.swift
+++ b/ios/Packages/Sybil/Sources/Sybil/SybilPhoneShellView.swift
@@ -242,6 +242,7 @@ struct SybilPhoneShellView: View {
     }
 
     private func showRoute(_ nextRoute: PhoneRoute) {
+        dismissSidebarKeyboard()
         let update = {
             route = nextRoute
         }
@@ -271,12 +272,19 @@ struct SybilPhoneShellView: View {
     }
 
     private func hideSidebarOverlay() {
+        dismissSidebarKeyboard()
         withAnimation(.easeOut(duration: 0.18)) {
             isSidebarOverlayPresented = false
         }
         resetSidebarSwipe(animated: false)
     }
 
+    private func dismissSidebarKeyboard() {
+        if isSidebarOverlayPresented {
+            UIApplication.shared.sendAction(#selector(UIResponder.resignFirstResponder), to: nil, from: nil, for: nil)
+        }
+    }
+
     private func openSidebarSelection(_ selection: SidebarSelection) {
         if openingSelectionRequestID != nil, sidebarHighlightSelection == selection {
             return
diff --git a/ios/Packages/Sybil/Sources/Sybil/SybilSidebarView.swift b/ios/Packages/Sybil/Sources/Sybil/SybilSidebarView.swift
index 02e9db2..0e11ad0 100644
--- a/ios/Packages/Sybil/Sources/Sybil/SybilSidebarView.swift
+++ b/ios/Packages/Sybil/Sources/Sybil/SybilSidebarView.swift
@@ -115,6 +115,7 @@ struct SybilSidebarItemList: View {
     var onOpenForkedChat: ((String) -> Void)? = nil
     @State private var renameTarget: SidebarItem?
     @State private var renameTitle = ""
+    @FocusState private var isSearchFocused: Bool
 
     private var isRenameAlertPresented: Binding<Bool> {
         Binding {
@@ -128,37 +129,98 @@ struct SybilSidebarItemList: View {
     }
 
     var body: some View {
+        VStack(spacing: 0) {
+            HStack(spacing: 10) {
+                Image(systemName: "magnifyingglass")
+                    .foregroundStyle(SybilTheme.textMuted)
+                TextField("Search chats and web searches", text: Binding(
+                    get: { viewModel.sidebarSearchQuery },
+                    set: { viewModel.setSidebarSearchQuery($0) }
+                ))
+                .font(.sybil(.subheadline))
+                .foregroundStyle(SybilTheme.text)
+                .textInputAutocapitalization(.never)
+                .autocorrectionDisabled()
+                .submitLabel(.search)
+                .focused($isSearchFocused)
+                .accessibilityLabel("Search conversation history and saved web searches")
+                .onSubmit {
+                    isSearchFocused = false
+                    Task { await viewModel.refreshSidebarSearch() }
+                }
+
+                if !viewModel.sidebarSearchQuery.isEmpty {
+                    Button {
+                        viewModel.setSidebarSearchQuery("")
+                    } label: {
+                        Image(systemName: "xmark.circle.fill")
+                            .foregroundStyle(SybilTheme.textMuted)
+                    }
+                    .buttonStyle(.plain)
+                    .accessibilityLabel("Clear history search")
+                }
+            }
+            .padding(12)
+            .background(SybilTheme.surface, in: RoundedRectangle(cornerRadius: 12))
+            .overlay(RoundedRectangle(cornerRadius: 12).stroke(SybilTheme.border, lineWidth: 1))
+            .padding(10)
+
+            itemList
+        }
+    }
+
+    private var itemList: some View {
         Group {
-            if viewModel.isLoadingCollections && viewModel.sidebarItems.isEmpty {
+            if viewModel.isSearchingSidebar ||
+                (!viewModel.isSidebarSearchActive && viewModel.isLoadingCollections && viewModel.sidebarItems.isEmpty) {
                 VStack(alignment: .leading, spacing: 8) {
                     ProgressView()
                         .tint(SybilTheme.primary)
-                    Text("Loading conversations…")
+                    Text(viewModel.isSidebarSearchActive ? "Searching history…" : "Loading conversations…")
                         .font(.sybil(.footnote))
                         .foregroundStyle(SybilTheme.textMuted)
                 }
                 .frame(maxWidth: .infinity, maxHeight: .infinity, alignment: .topLeading)
                 .padding(16)
-            } else if viewModel.sidebarItems.isEmpty {
+            } else if let error = viewModel.sidebarSearchError, viewModel.isSidebarSearchActive {
+                VStack(spacing: 12) {
+                    Text(error)
+                        .font(.sybil(.footnote))
+                        .foregroundStyle(SybilTheme.danger)
+                        .multilineTextAlignment(.center)
+                    Button("Try again") {
+                        Task { await viewModel.refreshSidebarSearch() }
+                    }
+                }
+                .frame(maxWidth: .infinity, maxHeight: .infinity)
+                .padding(16)
+            } else if viewModel.visibleSidebarItems.isEmpty {
                 VStack(spacing: 10) {
-                    Image(systemName: "message.badge")
+                    Image(systemName: viewModel.isSidebarSearchActive ? "magnifyingglass" : "message.badge")
                         .font(.system(size: 20, weight: .medium))
                         .foregroundStyle(SybilTheme.textMuted)
-                    Text("Start a chat or run your first search.")
+                    Text(viewModel.isSidebarSearchActive ? "No matching chats or web searches." : "Start a chat or run your first search.")
                         .font(.sybil(.footnote))
                         .multilineTextAlignment(.center)
                         .foregroundStyle(SybilTheme.textMuted)
+                    if viewModel.isSidebarSearchActive {
+                        Text("Try a title, a query, or words from a conversation.")
+                            .font(.sybil(.caption))
+                            .multilineTextAlignment(.center)
+                            .foregroundStyle(SybilTheme.textMuted)
+                    }
                 }
                 .frame(maxWidth: .infinity, maxHeight: .infinity)
                 .padding(16)
             } else {
                 ScrollView {
                     LazyVStack(alignment: .leading, spacing: 8) {
-                        ForEach(viewModel.sidebarItems) { item in
+                        ForEach(viewModel.visibleSidebarItems) { item in
                             Button {
+                                isSearchFocused = false
                                 onSelect(item)
                             } label: {
-                                SybilSidebarRow(item: item, isSelected: isSelected(item))
+                                SybilSidebarRow(item: item, isSelected: isSelected(item), searchQuery: viewModel.sidebarSearchQuery)
                             }
                             .buttonStyle(.plain)
                             .contextMenu {
@@ -201,9 +263,16 @@ struct SybilSidebarItemList: View {
                                 }
                             }
                         }
+                        if viewModel.isSidebarSearchActive && viewModel.sidebarSearchHasMore {
+                            Text("Showing the 100 most recent matches. Refine your search to find more.")
+                                .font(.sybil(.caption))
+                                .foregroundStyle(SybilTheme.textMuted)
+                                .padding(12)
+                        }
                     }
                     .padding(10)
                 }
+                .scrollDismissesKeyboard(.interactively)
                 .refreshable {
                     await viewModel.refreshSidebarCollectionsFromPullToRefresh()
                 }
@@ -257,6 +326,25 @@ struct SybilSidebarItemList: View {
 struct SybilSidebarRow: View {
     var item: SidebarItem
     var isSelected: Bool
+    var searchQuery = ""
+
+    private func highlightedSnippet(_ snippet: String) -> AttributedString {
+        var highlighted = AttributedString(snippet)
+        guard let words = try? NSRegularExpression(pattern: #"[\p{L}\p{N}\p{M}\p{Co}]+"#) else { return highlighted }
+        let terms = words.matches(in: searchQuery, range: NSRange(searchQuery.startIndex..., in: searchQuery)).compactMap { match -> String? in
+            guard let range = Range(match.range, in: searchQuery) else { return nil }
+            return String(searchQuery[range]).folding(options: [.diacriticInsensitive, .caseInsensitive], locale: Locale(identifier: "en_US_POSIX"))
+        }.filter { !$0.isEmpty }
+        for word in words.matches(in: snippet, range: NSRange(snippet.startIndex..., in: snippet)) {
+            guard let range = Range(word.range, in: snippet) else { continue }
+            let normalized = String(snippet[range]).folding(options: [.diacriticInsensitive, .caseInsensitive], locale: Locale(identifier: "en_US_POSIX"))
+            guard terms.contains(where: { normalized.hasPrefix($0) }),
+                  let start = AttributedString.Index(range.lowerBound, within: highlighted),
+                  let end = AttributedString.Index(range.upperBound, within: highlighted) else { continue }
+            highlighted[start..<end].font = .sybil(.caption, weight: .semibold)
+        }
+        return highlighted
+    }
 
     private var isHighlighted: Bool {
         isSelected
@@ -318,6 +406,15 @@ struct SybilSidebarRow: View {
                         .frame(maxWidth: .infinity, alignment: .trailing)
                 }
             }
+
+            if let snippet = item.searchSnippet, !snippet.isEmpty {
+                Text(highlightedSnippet(snippet.replacingOccurrences(of: #"\s+"#, with: " ", options: .regularExpression)))
+                    .font(.sybil(.caption))
+                    .foregroundStyle(SybilTheme.textMuted)
+                    .lineLimit(1)
+                    .truncationMode(.middle)
+                    .multilineTextAlignment(.leading)
+            }
         }
         .foregroundStyle(SybilTheme.text)
         .padding(.horizontal, 12)
diff --git a/ios/Packages/Sybil/Sources/Sybil/SybilViewModel.swift b/ios/Packages/Sybil/Sources/Sybil/SybilViewModel.swift
index c94a4dc..f7cbb34 100644
--- a/ios/Packages/Sybil/Sources/Sybil/SybilViewModel.swift
+++ b/ios/Packages/Sybil/Sources/Sybil/SybilViewModel.swift
@@ -38,6 +38,7 @@ struct SidebarItem: Identifiable, Hashable {
     var starredAt: Date?
     var initiatedLabel: String?
     var isRunning: Bool
+    var searchSnippet: String? = nil
 }
 
 enum StreamingAssistantContentUpdate: Equatable, Sendable {
@@ -161,6 +162,15 @@ final class SybilViewModel {
     var chats: [ChatSummary] = []
     var searches: [SearchSummary] = []
     var workspaceItems: [WorkspaceItem] = []
+    private(set) var sidebarSearchQuery = ""
+    private(set) var sidebarSearchResults: [WorkspaceItem] = []
+    private(set) var isSearchingSidebar = false
+    private(set) var sidebarSearchError: String?
+    private(set) var sidebarSearchHasMore = false
+    @ObservationIgnored
+    private var sidebarSearchTask: Task<Void, Never>?
+    @ObservationIgnored
+    private var sidebarSearchRequestID = UUID()
 
     var selectedItem: SidebarSelection?
     var selectedChat: ChatDetail?
@@ -482,7 +492,19 @@ final class SybilViewModel {
     }
 
     var sidebarItems: [SidebarItem] {
-        workspaceItems.map { item in
+        makeSidebarItems(workspaceItems)
+    }
+
+    var isSidebarSearchActive: Bool {
+        !sidebarSearchQuery.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty
+    }
+
+    var visibleSidebarItems: [SidebarItem] {
+        isSidebarSearchActive ? makeSidebarItems(sidebarSearchResults) : sidebarItems
+    }
+
+    private func makeSidebarItems(_ items: [WorkspaceItem]) -> [SidebarItem] {
+        items.map { item in
             switch item.type {
             case .chat:
                 let initiatedLabel: String?
@@ -496,7 +518,8 @@ final class SybilViewModel {
                     initiatedLabel = nil
                 }
                 let starOwner = item.parentChatId.flatMap { parentChatID in
-                    workspaceItems.first(where: { $0.type == .chat && $0.id == parentChatID })
+                    workspaceItems.first(where: { $0.type == .chat && $0.id == parentChatID }) ??
+                        sidebarSearchResults.first(where: { $0.type == .chat && $0.id == parentChatID })
                 } ?? item
 
                 return SidebarItem(
@@ -507,7 +530,8 @@ final class SybilViewModel {
                     starred: starOwner.starred,
                     starredAt: starOwner.starredAt,
                     initiatedLabel: initiatedLabel,
-                    isRunning: isChatRowRunning(item.id)
+                    isRunning: isChatRowRunning(item.id),
+                    searchSnippet: item.searchSnippet
                 )
 
             case .search:
@@ -519,20 +543,70 @@ final class SybilViewModel {
                     starred: item.starred,
                     starredAt: item.starredAt,
                     initiatedLabel: "exa",
-                    isRunning: isSearchRowRunning(item.id)
+                    isRunning: isSearchRowRunning(item.id),
+                    searchSnippet: item.searchSnippet
                 )
             }
         }
     }
 
+    func setSidebarSearchQuery(_ query: String) {
+        let previous = sidebarSearchQuery.trimmingCharacters(in: .whitespacesAndNewlines)
+        sidebarSearchQuery = query
+        guard query.trimmingCharacters(in: .whitespacesAndNewlines) != previous else { return }
+        scheduleSidebarSearch()
+    }
+
+    func refreshSidebarSearch() async {
+        guard isSidebarSearchActive else { return }
+        scheduleSidebarSearch(debounce: false)
+        await sidebarSearchTask?.value
+    }
+
+    private func scheduleSidebarSearch(debounce: Bool = true) {
+        sidebarSearchTask?.cancel()
+        let requestID = UUID()
+        sidebarSearchRequestID = requestID
+        sidebarSearchResults = []
+        sidebarSearchError = nil
+        sidebarSearchHasMore = false
+        isSearchingSidebar = false
+        let query = sidebarSearchQuery.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !query.isEmpty, isAuthenticated else { return }
+        guard query.utf16.count <= 200 else {
+            sidebarSearchError = "Use 200 characters or fewer."
+            return
+        }
+        isSearchingSidebar = true
+        sidebarSearchTask = Task { [weak self] in
+            do {
+                if debounce { try await Task.sleep(for: .milliseconds(300)) }
+                guard let self, !Task.isCancelled else { return }
+                let response = try await self.client().searchWorkspaceItems(query: query)
+                guard !Task.isCancelled, self.sidebarSearchRequestID == requestID else { return }
+                self.sidebarSearchResults = response.items
+                self.sidebarSearchHasMore = response.hasMore
+                self.isSearchingSidebar = false
+            } catch {
+                guard let self, !Task.isCancelled, self.sidebarSearchRequestID == requestID else { return }
+                self.isSearchingSidebar = false
+                if !self.isCancellation(error) {
+                    self.sidebarSearchError = self.normalizeAPIError(error)
+                }
+            }
+        }
+    }
+
     var selectedChatSummary: ChatSummary? {
         guard case let .chat(chatID) = selectedItem else { return nil }
-        return chats.first(where: { $0.id == chatID })
+        return chats.first(where: { $0.id == chatID }) ??
+            sidebarSearchResults.first(where: { $0.type == .chat && $0.id == chatID })?.chatSummary
     }
 
     var selectedSearchSummary: SearchSummary? {
         guard case let .search(searchID) = selectedItem else { return nil }
-        return searches.first(where: { $0.id == searchID })
+        return searches.first(where: { $0.id == searchID }) ??
+            sidebarSearchResults.first(where: { $0.type == .search && $0.id == searchID })?.searchSummary
     }
 
     var hasRefreshableSelection: Bool {
@@ -559,6 +633,7 @@ final class SybilViewModel {
     }
 
     func reconnect() async {
+        setSidebarSearchQuery("")
         isCheckingSession = true
         authError = nil
         errorMessage = nil
@@ -865,6 +940,15 @@ final class SybilViewModel {
     private func beginSelecting(_ selection: SidebarSelection) -> Task<Void, Never>? {
         SybilLog.debug(SybilLog.ui, "Selecting \(selection.id)")
 
+        // Search can open history outside the recent collection. Retain its
+        // summary for provider settings, starring, and subsequent refreshes.
+        if let item = sidebarSearchResults.first(where: {
+            ($0.type == .chat ? SidebarSelection.chat($0.id) : .search($0.id)) == selection
+        }) {
+            if let chat = item.chatSummary { applyChatSummary(chat, moveToFront: false) }
+            if let search = item.searchSummary { applySearchSummary(search, moveToFront: false) }
+        }
+
         if draftKind == nil, selectedItem == selection {
             errorMessage = nil
             if case .search = selection {
@@ -915,7 +999,7 @@ final class SybilViewModel {
     }
 
     private func selectAdjacentSidebarItem(offset: Int) {
-        let items = sidebarItems
+        let items = visibleSidebarItems
         guard !items.isEmpty else {
             return
         }
@@ -951,6 +1035,7 @@ final class SybilViewModel {
                     break
                 }
                 await refreshCollections(preferredSelection: nil)
+                await refreshSidebarSearch()
             } catch {
                 errorMessage = normalizeAPIError(error)
                 SybilLog.error(SybilLog.ui, "Delete failed", error: error)
@@ -1006,6 +1091,7 @@ final class SybilViewModel {
         do {
             let updated = try await client().updateChatTitle(chatID: chatID, title: trimmedTitle)
             applyChatSummary(updated, moveToFront: true)
+            await refreshSidebarSearch()
         } catch {
             errorMessage = normalizeAPIError(error)
             SybilLog.error(SybilLog.ui, "Rename failed", error: error)
@@ -1105,6 +1191,10 @@ final class SybilViewModel {
     }
 
     func refreshSidebarCollectionsFromPullToRefresh() async {
+        if isSidebarSearchActive {
+            await refreshSidebarSearch()
+            return
+        }
         guard isAuthenticated, !isCheckingSession else {
             return
         }
@@ -1445,7 +1535,15 @@ final class SybilViewModel {
             async let activeRunsValue = client.getActiveRuns()
             let (nextWorkspaceItems, nextActiveRuns) = try await (workspaceItemsValue, activeRunsValue)
 
-            applyWorkspaceItems(nextWorkspaceItems)
+            var items = nextWorkspaceItems
+            // A selected historical search result may be outside the latest 100.
+            if let preferredSelection,
+               let selectedSummary = workspaceItems.first(where: {
+                   ($0.type == .chat ? SidebarSelection.chat($0.id) : .search($0.id)) == preferredSelection
+               }), !items.contains(where: { $0.type == selectedSummary.type && $0.id == selectedSummary.id }) {
+                items.append(selectedSummary)
+            }
+            applyWorkspaceItems(items)
             applyActiveRuns(nextActiveRuns)
 
             SybilLog.info(
@@ -1623,6 +1721,11 @@ final class SybilViewModel {
     }
 
     private func upsertWorkspaceItem(_ item: WorkspaceItem, moveToFront: Bool) {
+        if let index = sidebarSearchResults.firstIndex(where: { $0.type == item.type && $0.id == item.id }) {
+            var updated = item
+            updated.searchSnippet = sidebarSearchResults[index].searchSnippet
+            sidebarSearchResults[index] = updated
+        }
         if let existingIndex = workspaceItems.firstIndex(where: { $0.type == item.type && $0.id == item.id }) {
             workspaceItems.remove(at: existingIndex)
             if moveToFront {
@@ -1646,6 +1749,9 @@ final class SybilViewModel {
         if let parentChatID = workspaceItems.first(where: { $0.type == .chat && $0.id == chatID })?.parentChatId {
             return parentChatID
         }
+        if let parentChatID = sidebarSearchResults.first(where: { $0.type == .chat && $0.id == chatID })?.parentChatId {
+            return parentChatID
+        }
         return chatID
     }
 
diff --git a/ios/Packages/Sybil/Tests/SybilTests/SybilTests.swift b/ios/Packages/Sybil/Tests/SybilTests/SybilTests.swift
index 2898ae1..23a8b5c 100644
--- a/ios/Packages/Sybil/Tests/SybilTests/SybilTests.swift
+++ b/ios/Packages/Sybil/Tests/SybilTests/SybilTests.swift
@@ -9,6 +9,7 @@ import UIKit
 
 private struct MockClientCallSnapshot: Sendable {
     var listWorkspaceItems = 0
+    var workspaceSearchQueries: [String] = []
     var listChats = 0
     var listSearches = 0
     var createChat = 0
@@ -43,6 +44,7 @@ private actor MockSybilClient: SybilAPIClienting {
     private let chatsResponse: [ChatSummary]
     private let searchesResponse: [SearchSummary]
     private let workspaceItemsResponse: [WorkspaceItem]
+    private let workspaceSearchHandler: @Sendable (String) async throws -> WorkspaceSearchResponse
     private let chatDetails: [String: ChatDetail]
     private let searchDetails: [String: SearchDetail]
     private let createChatResponse: ChatSummary?
@@ -86,11 +88,15 @@ private actor MockSybilClient: SybilAPIClienting {
         updateSearchStarResponses: [String: SearchSummary] = [:],
         activeRunsResponse: ActiveRunsResponse = ActiveRunsResponse(),
         workspaceItemsResponse: [WorkspaceItem]? = nil,
+        workspaceSearchHandler: @escaping @Sendable (String) async throws -> WorkspaceSearchResponse = { _ in
+            WorkspaceSearchResponse(items: [], hasMore: false)
+        },
         modelCatalogResponse: ModelCatalogResponse = ModelCatalogResponse(providers: [:])
     ) {
         self.chatsResponse = chatsResponse
         self.searchesResponse = searchesResponse
         self.workspaceItemsResponse = workspaceItemsResponse ?? Self.makeWorkspaceItems(chats: chatsResponse, searches: searchesResponse)
+        self.workspaceSearchHandler = workspaceSearchHandler
         self.chatDetails = chatDetails
         self.searchDetails = searchDetails
         self.createChatResponse = createChatResponse
@@ -186,6 +192,11 @@ private actor MockSybilClient: SybilAPIClienting {
         return workspaceItemsResponse
     }
 
+    func searchWorkspaceItems(query: String) async throws -> WorkspaceSearchResponse {
+        snapshot.workspaceSearchQueries.append(query)
+        return try await workspaceSearchHandler(query)
+    }
+
     func listChats() async throws -> [ChatSummary] {
         snapshot.listChats += 1
         if listChatsDelayNanoseconds > 0 {
@@ -1998,3 +2009,173 @@ private final class MockQuickQuestionLifecycle {
     controller.stop()
 }
 #endif
+
+// Deliberately ignores cancellation so stale-response protection is exercised.
+private actor WorkspaceSearchGate {
+    private var pending: [String: CheckedContinuation<WorkspaceSearchResponse, any Error>] = [:]
+    private var observers: [String: CheckedContinuation<Void, Never>] = [:]
+
+    func response(for query: String) async throws -> WorkspaceSearchResponse {
+        try await withCheckedThrowingContinuation { continuation in
+            pending[query] = continuation
+            observers.removeValue(forKey: query)?.resume()
+        }
+    }
+
+    func waitUntilRequested(_ query: String) async {
+        if pending[query] != nil { return }
+        await withCheckedContinuation { observers[query] = $0 }
+    }
+
+    func complete(_ query: String, with response: WorkspaceSearchResponse) {
+        pending.removeValue(forKey: query)?.resume(returning: response)
+    }
+
+    func fail(_ query: String) {
+        pending.removeValue(forKey: query)?.resume(throwing: APIError.networkError(message: "Offline"))
+    }
+}
+
+@MainActor
+@Test func historySearchKeepsRecentItemsAndOpensOlderChat() async throws {
+    let date = Date(timeIntervalSince1970: 1_700_000_000)
+    let recent = makeChatSummary(id: "recent", date: date)
+    let old = makeChatSummary(id: "old", date: date.addingTimeInterval(-100))
+    var match = WorkspaceItem(chat: old)
+    match.searchSnippet = "The nebula we discussed"
+    let response = WorkspaceSearchResponse(items: [match, WorkspaceItem(search: makeSearchSummary(id: "web", date: date))], hasMore: true)
+    let client = MockSybilClient(
+        chatsResponse: [recent],
+        chatDetails: ["old": makeChatDetail(id: "old", date: date, body: "The nebula we discussed")],
+        workspaceSearchHandler: { _ in response }
+    )
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    viewModel.isCheckingSession = false
+    viewModel.workspaceItems = [WorkspaceItem(chat: recent)]
+    viewModel.chats = [recent]
+    viewModel.selectedItem = .chat("recent")
+    viewModel.setSidebarSearchQuery("  nebula  ")
+    await viewModel.refreshSidebarSearch()
+    #expect(viewModel.selectedItem == .chat("recent"))
+    #expect(viewModel.workspaceItems == [WorkspaceItem(chat: recent)])
+    #expect(viewModel.visibleSidebarItems.map(\.selection) == [.chat("old"), .search("web")])
+    #expect(viewModel.visibleSidebarItems.first?.searchSnippet == "The nebula we discussed")
+    #expect(viewModel.sidebarSearchHasMore)
+    #expect(await client.currentSnapshot().workspaceSearchQueries == ["nebula"])
+    await viewModel.selectForNavigation(.chat("old"))
+    #expect(viewModel.selectedChat?.id == "old")
+    viewModel.setSidebarSearchQuery("")
+    await viewModel.refreshVisibleContent(refreshCollections: true, refreshSelection: false)
+    #expect(viewModel.selectedItem == .chat("old"))
+    #expect(viewModel.selectedChat?.id == "old")
+    #expect(viewModel.sidebarItems.contains(where: { $0.selection == .chat("old") }))
+}
+
+@MainActor
+@Test func historySearchDebouncesAndClearingRestoresRecentItems() async throws {
+    let client = MockSybilClient()
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    let recent = WorkspaceItem(chat: makeChatSummary(id: "recent", date: Date()))
+    viewModel.workspaceItems = [recent]
+    viewModel.setSidebarSearchQuery("n")
+    viewModel.setSidebarSearchQuery("ne")
+    viewModel.setSidebarSearchQuery("nebula")
+    #expect(viewModel.isSearchingSidebar)
+    #expect(await client.currentSnapshot().workspaceSearchQueries.isEmpty)
+    try await Task.sleep(for: .milliseconds(600))
+    #expect(await client.currentSnapshot().workspaceSearchQueries == ["nebula"])
+    #expect(viewModel.visibleSidebarItems.isEmpty)
+    #expect(!viewModel.isSearchingSidebar)
+    viewModel.setSidebarSearchQuery("   ")
+    #expect(viewModel.visibleSidebarItems.map(\.selection) == [.chat("recent")])
+    #expect(!viewModel.isSidebarSearchActive)
+    #expect(viewModel.sidebarSearchError == nil)
+}
+
+@MainActor
+@Test func historySearchDiscardsOutOfOrderAndClearedResponses() async throws {
+    let gate = WorkspaceSearchGate()
+    let client = MockSybilClient(workspaceSearchHandler: { try await gate.response(for: $0) })
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    viewModel.setSidebarSearchQuery("first")
+    let first = Task { await viewModel.refreshSidebarSearch() }
+    await gate.waitUntilRequested("first")
+    viewModel.setSidebarSearchQuery("second")
+    let second = Task { await viewModel.refreshSidebarSearch() }
+    await gate.waitUntilRequested("second")
+    let match = WorkspaceItem(chat: makeChatSummary(id: "second", date: Date()))
+    await gate.complete("second", with: WorkspaceSearchResponse(items: [match], hasMore: false))
+    await second.value
+    await gate.fail("first")
+    await first.value
+    #expect(viewModel.sidebarSearchResults == [match])
+    #expect(viewModel.sidebarSearchError == nil)
+    #expect(!viewModel.isSearchingSidebar)
+
+    viewModel.setSidebarSearchQuery("third")
+    let third = Task { await viewModel.refreshSidebarSearch() }
+    await gate.waitUntilRequested("third")
+    viewModel.setSidebarSearchQuery("")
+    await gate.complete("third", with: WorkspaceSearchResponse(items: [match], hasMore: true))
+    await third.value
+    #expect(viewModel.sidebarSearchResults.isEmpty)
+    #expect(!viewModel.sidebarSearchHasMore)
+    #expect(!viewModel.isSearchingSidebar)
+}
+
+@MainActor
+@Test func historySearchFailureCanRetryWithoutChangingSelection() async throws {
+    let gate = WorkspaceSearchGate()
+    let client = MockSybilClient(workspaceSearchHandler: { try await gate.response(for: $0) })
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    viewModel.selectedItem = .chat("current")
+    viewModel.setSidebarSearchQuery("nebula")
+    let failed = Task { await viewModel.refreshSidebarSearch() }
+    await gate.waitUntilRequested("nebula")
+    await gate.fail("nebula")
+    await failed.value
+    #expect(viewModel.sidebarSearchError != nil)
+    #expect(viewModel.selectedItem == .chat("current"))
+    let retry = Task { await viewModel.refreshSidebarSearch() }
+    await gate.waitUntilRequested("nebula")
+    await gate.complete("nebula", with: WorkspaceSearchResponse(items: [], hasMore: false))
+    await retry.value
+    #expect(viewModel.sidebarSearchError == nil)
+    #expect(!viewModel.isSearchingSidebar)
+    #expect(viewModel.selectedItem == .chat("current"))
+    viewModel.setSidebarSearchQuery(String(repeating: "a", count: 201))
+    #expect(viewModel.sidebarSearchError == "Use 200 characters or fewer.")
+    #expect(await client.currentSnapshot().workspaceSearchQueries == ["nebula", "nebula"])
+}
+
+private final class HistorySearchURLProtocol: URLProtocol, @unchecked Sendable {
+    override class func canInit(with request: URLRequest) -> Bool { true }
+    override class func canonicalRequest(for request: URLRequest) -> URLRequest { request }
+    override func startLoading() {
+        let url = request.url!
+        #expect(url.path == "/api/v1/workspace-items")
+        #expect(request.httpMethod == "GET")
+        #expect(request.value(forHTTPHeaderField: "Authorization") == "Bearer test-token")
+        #expect(URLComponents(url: url, resolvingAgainstBaseURL: false)?.queryItems == [URLQueryItem(name: "q", value: "café + AI & #ideas?")])
+        let json = #"{"items":[{"type":"chat","id":"old","title":"Notes","createdAt":"2026-01-01T00:00:00.000Z","updatedAt":"2026-01-01T00:00:00.000Z","searchSnippet":"Some café ideas"}],"hasMore":false}"#
+        client?.urlProtocol(self, didReceive: HTTPURLResponse(url: url, statusCode: 200, httpVersion: nil, headerFields: ["Content-Type": "application/json"])!, cacheStoragePolicy: .notAllowed)
+        client?.urlProtocol(self, didLoad: Data(json.utf8))
+        client?.urlProtocolDidFinishLoading(self)
+    }
+    override func stopLoading() {}
+}
+
+@Test func historySearchEncodesQueryAndDecodesSnippet() async throws {
+    let configuration = URLSessionConfiguration.ephemeral
+    configuration.protocolClasses = [HistorySearchURLProtocol.self]
+    let session = URLSession(configuration: configuration)
+    defer { session.invalidateAndCancel() }
+    let client = SybilAPIClient(configuration: APIConfiguration(baseURL: URL(string: "https://example.com/api")!, authToken: "test-token"), session: session)
+    let response = try await client.searchWorkspaceItems(query: "café + AI & #ideas?")
+    #expect(response.items.first?.searchSnippet == "Some café ideas")
+    #expect(!response.hasMore)
+}
diff --git a/ios/README.md b/ios/README.md
index 9b79dbc..d4b1003 100644
--- a/ios/README.md
+++ b/ios/README.md
@@ -5,6 +5,14 @@ Run `just run` for the iPhone simulator, or `just run-mac` for Mac Catalyst.
 project from `project.yml`. The Mac recipes use ad-hoc signing for local development;
 release/archive signing settings are unchanged.
 
+The conversation sidebar includes **Search chats and web searches** on iPhone,
+iPad, and Mac. It searches all saved history by title, conversation text, and saved
+web-search query/answer, with single-line excerpts that bold matching words and
+truncate in the middle. Search waits briefly while typing,
+cancels superseded requests, and leaves the current conversation open. Clear the
+field to return to recent items. Searches use word prefixes (for example, `plan`
+finds `planning`); if more than 100 items match, refine the query.
+
 ## Quick Question on macOS
 
 While the Catalyst app is running, **Option+Space** toggles a floating Quick
diff --git a/server/prisma/migrations/20261007000000_add_workspace_full_text_search/migration.sql b/server/prisma/migrations/20261007000000_add_workspace_full_text_search/migration.sql
new file mode 100644
index 0000000..95a2f03
--- /dev/null
+++ b/server/prisma/migrations/20261007000000_add_workspace_full_text_search/migration.sql
@@ -0,0 +1,70 @@
+-- External-content indexes avoid storing a second copy of conversation text.
+-- Keep these virtual tables and triggers in SQL: Prisma does not model FTS5.
+CREATE VIRTUAL TABLE "ChatSearch" USING fts5(
+  title, content='Chat', content_rowid='rowid',
+  tokenize='unicode61 remove_diacritics 2', prefix='1 2 3'
+);
+
+-- Hidden system prompts and tool payloads are not searchable conversation text.
+CREATE VIEW "MessageSearchContent" AS
+  SELECT rowid, content FROM "Message" WHERE role IN ('user', 'assistant');
+CREATE VIRTUAL TABLE "MessageSearch" USING fts5(
+  content, content='MessageSearchContent', content_rowid='rowid',
+  tokenize='unicode61 remove_diacritics 2', prefix='1 2 3'
+);
+
+CREATE VIRTUAL TABLE "SavedSearchSearch" USING fts5(
+  title, query, answerText, content='Search', content_rowid='rowid',
+  tokenize='unicode61 remove_diacritics 2', prefix='1 2 3'
+);
+
+CREATE TRIGGER "ChatSearch_insert" AFTER INSERT ON "Chat" BEGIN
+  INSERT INTO "ChatSearch" (rowid, title) VALUES (new.rowid, new.title);
+END;
+CREATE TRIGGER "ChatSearch_delete" AFTER DELETE ON "Chat" BEGIN
+  INSERT INTO "ChatSearch" ("ChatSearch", rowid, title) VALUES ('delete', old.rowid, old.title);
+END;
+CREATE TRIGGER "ChatSearch_update" AFTER UPDATE OF title ON "Chat"
+WHEN old.title IS NOT new.title BEGIN
+  INSERT INTO "ChatSearch" ("ChatSearch", rowid, title) VALUES ('delete', old.rowid, old.title);
+  INSERT INTO "ChatSearch" (rowid, title) VALUES (new.rowid, new.title);
+END;
+
+CREATE TRIGGER "MessageSearch_insert" AFTER INSERT ON "Message"
+WHEN new.role IN ('user', 'assistant') BEGIN
+  INSERT INTO "MessageSearch" (rowid, content) VALUES (new.rowid, new.content);
+END;
+CREATE TRIGGER "MessageSearch_delete" AFTER DELETE ON "Message"
+WHEN old.role IN ('user', 'assistant') BEGIN
+  INSERT INTO "MessageSearch" ("MessageSearch", rowid, content) VALUES ('delete', old.rowid, old.content);
+END;
+CREATE TRIGGER "MessageSearch_update" AFTER UPDATE OF content, role ON "Message"
+WHEN old.content IS NOT new.content OR old.role IS NOT new.role BEGIN
+  INSERT INTO "MessageSearch" ("MessageSearch", rowid, content)
+    SELECT 'delete', old.rowid, old.content WHERE old.role IN ('user', 'assistant');
+  INSERT INTO "MessageSearch" (rowid, content)
+    SELECT new.rowid, new.content WHERE new.role IN ('user', 'assistant');
+END;
+
+CREATE TRIGGER "SavedSearchSearch_insert" AFTER INSERT ON "Search" BEGIN
+  INSERT INTO "SavedSearchSearch" (rowid, title, query, answerText)
+    VALUES (new.rowid, new.title, new.query, new.answerText);
+END;
+CREATE TRIGGER "SavedSearchSearch_delete" AFTER DELETE ON "Search" BEGIN
+  INSERT INTO "SavedSearchSearch" ("SavedSearchSearch", rowid, title, query, answerText)
+    VALUES ('delete', old.rowid, old.title, old.query, old.answerText);
+END;
+CREATE TRIGGER "SavedSearchSearch_update" AFTER UPDATE OF title, query, answerText ON "Search"
+WHEN old.title IS NOT new.title OR old.query IS NOT new.query OR old.answerText IS NOT new.answerText BEGIN
+  INSERT INTO "SavedSearchSearch" ("SavedSearchSearch", rowid, title, query, answerText)
+    VALUES ('delete', old.rowid, old.title, old.query, old.answerText);
+  INSERT INTO "SavedSearchSearch" (rowid, title, query, answerText)
+    VALUES (new.rowid, new.title, new.query, new.answerText);
+END;
+
+-- Index existing history during migration, then maintain it transactionally.
+INSERT INTO "ChatSearch" ("ChatSearch") VALUES ('rebuild');
+INSERT INTO "MessageSearch" ("MessageSearch") VALUES ('rebuild');
+INSERT INTO "SavedSearchSearch" ("SavedSearchSearch") VALUES ('rebuild');
+
+CREATE INDEX "Chat_updatedAt_idx" ON "Chat"("updatedAt");
diff --git a/server/prisma/schema.prisma b/server/prisma/schema.prisma
index 7b205c4..08800bb 100644
--- a/server/prisma/schema.prisma
+++ b/server/prisma/schema.prisma
@@ -76,6 +76,7 @@ model Chat {
 
   @@index([userId])
   @@index([parentChatId])
+  @@index([updatedAt])
 }
 
 model Message {
diff --git a/server/src/routes.ts b/server/src/routes.ts
index 538d8fa..29ee56b 100644
--- a/server/src/routes.ts
+++ b/server/src/routes.ts
@@ -16,6 +16,7 @@ import { openaiClient } from "./llm/providers.js";
 import { serializeProviderFields, toPrismaProvider } from "./llm/provider-ids.js";
 import { exaClient } from "./search/exa.js";
 import { isFreshSearchCacheHit, normalizeSearchQuery } from "./search-cache.js";
+import { searchWorkspace } from "./workspace-search.js";
 import type { ChatAttachment } from "./llm/types.js";
 
 const ProviderSchema = z.enum(["openai", "anthropic", "xai", "gemini", "hermes-agent"]);
@@ -927,6 +928,37 @@ export async function registerRoutes(app: FastifyInstance) {
 
   app.get("/v1/workspace-items", async (req) => {
     requireAdmin(req);
+    const parsed = z.object({ q: z.string().trim().max(200).optional() }).safeParse(req.query);
+    if (!parsed.success) throw app.httpErrors.badRequest("q must be a string of at most 200 characters");
+    if (parsed.data.q) {
+      const { hits, hasMore } = await searchWorkspace(parsed.data.q);
+      const [chats, searches] = await Promise.all([
+        prisma.chat.findMany({
+          where: { id: { in: hits.filter((hit) => hit.type === "chat").map((hit) => hit.id) } },
+          select: {
+            ...chatSummarySelect,
+            parentChat: { select: { projectItems: starredProjectItemsSelect } },
+          },
+        }),
+        prisma.search.findMany({
+          where: { id: { in: hits.filter((hit) => hit.type === "search").map((hit) => hit.id) } },
+          select: searchSummarySelect,
+        }),
+      ]);
+      const summaries = new Map<string, Record<string, unknown>>([
+        ...chats.map(({ parentChat, ...chat }) => [
+          `chat:${chat.id}`,
+          // Search omits unmatched roots, but sidebar fork stars belong to the root.
+          { ...serializeChatLike(chat), ...serializeStarFields(parentChat ?? chat) },
+        ] as const),
+        ...searches.map((search) => [`search:${search.id}`, serializeSearchLike(search)] as const),
+      ]);
+      const items = hits.flatMap((hit) => {
+        const summary = summaries.get(`${hit.type}:${hit.id}`);
+        return summary ? [{ ...summary, ...hit }] : [];
+      });
+      return { items, hasMore };
+    }
     return { items: await listWorkspaceItems() };
   });
 
diff --git a/server/src/workspace-search.ts b/server/src/workspace-search.ts
new file mode 100644
index 0000000..b9f8f92
--- /dev/null
+++ b/server/src/workspace-search.ts
@@ -0,0 +1,74 @@
+import { Prisma } from "@prisma/client";
+import { prisma } from "./db.js";
+
+export const WORKSPACE_SEARCH_LIMIT = 100;
+
+// Treat input as literal Unicode words, never FTS operators/column expressions.
+// Prefix matching supports type-ahead, including short terms such as "AI".
+export function workspaceSearchExpression(query: string): string | null {
+  const words = query.match(/[\p{L}\p{N}\p{M}\p{Co}]+/gu);
+  return words?.map((word) => `"${word}"*`).join(" AND ") ?? null;
+}
+
+export type WorkspaceSearchHit = {
+  type: "chat" | "search";
+  id: string;
+  searchSnippet: string | null;
+};
+
+export function workspaceSearchSQL(expression: string) {
+  // Batch excerpts after limiting matches. Unary + prevents SQLite from using
+  // the IN clause as repeated rowid lookups (and restarting FTS for every row).
+  // FTS still uses MATCH and the rowid bounds; IN filters that single scan.
+  return Prisma.sql`
+    WITH chat_hits AS (
+      SELECT c.id, NULL AS message_rowid
+      FROM "ChatSearch" JOIN "Chat" c ON c.rowid = "ChatSearch".rowid
+      WHERE "ChatSearch" MATCH ${expression}
+      UNION ALL
+      SELECT m.chatId AS id, MIN(m.rowid) AS message_rowid
+      FROM "MessageSearch" JOIN "Message" m ON m.rowid = "MessageSearch".rowid
+      WHERE "MessageSearch" MATCH ${expression}
+      GROUP BY m.chatId
+    ), matches AS (
+      SELECT 'chat' AS type, c.id, c.updatedAt, MIN(h.message_rowid) AS message_rowid,
+        NULL AS search_rowid
+      FROM chat_hits h JOIN "Chat" c ON c.id = h.id
+      GROUP BY c.id
+      UNION ALL
+      SELECT 'search' AS type, s.id, s.updatedAt, NULL AS message_rowid, s.rowid AS search_rowid
+      FROM "SavedSearchSearch" JOIN "Search" s ON s.rowid = "SavedSearchSearch".rowid
+      WHERE "SavedSearchSearch" MATCH ${expression}
+    ), limited AS MATERIALIZED (
+      SELECT * FROM matches ORDER BY updatedAt DESC, type, id LIMIT ${WORKSPACE_SEARCH_LIMIT + 1}
+    ), message_excerpts AS MATERIALIZED (
+      SELECT rowid, substr(snippet("MessageSearch", 0, '', '', ' … ', 24), 1, 480) AS snippet
+      FROM "MessageSearch"
+      WHERE "MessageSearch" MATCH ${expression}
+        AND rowid >= (SELECT MIN(message_rowid) FROM limited)
+        AND rowid <= (SELECT MAX(message_rowid) FROM limited)
+        AND +rowid IN (SELECT message_rowid FROM limited)
+    ), search_excerpts AS MATERIALIZED (
+      SELECT rowid, substr(snippet("SavedSearchSearch", -1, '', '', ' … ', 24), 1, 480) AS snippet
+      FROM "SavedSearchSearch"
+      WHERE "SavedSearchSearch" MATCH ${expression}
+        AND rowid >= (SELECT MIN(search_rowid) FROM limited)
+        AND rowid <= (SELECT MAX(search_rowid) FROM limited)
+        AND +rowid IN (SELECT search_rowid FROM limited)
+    )
+    SELECT type, id, COALESCE(m.snippet, s.snippet) AS searchSnippet
+    FROM limited
+    LEFT JOIN message_excerpts m ON m.rowid = limited.message_rowid
+    LEFT JOIN search_excerpts s ON s.rowid = limited.search_rowid
+    ORDER BY updatedAt DESC, type, id
+  `;
+}
+
+export async function searchWorkspace(query: string) {
+  const expression = workspaceSearchExpression(query);
+  if (!expression) return { hits: [], hasMore: false };
+  // Match via the inverted indexes first. Hydrate summaries and generate excerpts
+  // only for the bounded result set, never fetch full transcripts into JS.
+  const hits = await prisma.$queryRaw<WorkspaceSearchHit[]>(workspaceSearchSQL(expression));
+  return { hits: hits.slice(0, WORKSPACE_SEARCH_LIMIT), hasMore: hits.length > WORKSPACE_SEARCH_LIMIT };
+}
diff --git a/server/tests/chat-forks.test.ts b/server/tests/chat-forks.test.ts
index 25b9c3b..644f00c 100644
--- a/server/tests/chat-forks.test.ts
+++ b/server/tests/chat-forks.test.ts
@@ -1,6 +1,6 @@
 import assert from "node:assert/strict";
 import { execFileSync } from "node:child_process";
-import { mkdtempSync, rmSync } from "node:fs";
+import { mkdtempSync, rmSync, writeFileSync } from "node:fs";
 import { tmpdir } from "node:os";
 import { dirname, join, resolve } from "node:path";
 import test from "node:test";
@@ -11,6 +11,7 @@ import sensible from "@fastify/sensible";
 const serverRoot = resolve(dirname(fileURLToPath(import.meta.url)), "..");
 const databaseDir = mkdtempSync(join(tmpdir(), "sybil-chat-forks-"));
 process.env.DATABASE_URL = `file:${join(databaseDir, "test.db")}`;
+writeFileSync(join(databaseDir, "test.db"), "");
 process.env.OPENAI_API_KEY = "";
 delete process.env.ADMIN_TOKEN;
 
diff --git a/server/tests/workspace-search.test.ts b/server/tests/workspace-search.test.ts
new file mode 100644
index 0000000..a748d5b
--- /dev/null
+++ b/server/tests/workspace-search.test.ts
@@ -0,0 +1,188 @@
+import assert from "node:assert/strict";
+import { execFileSync } from "node:child_process";
+import { cpSync, mkdtempSync, readdirSync, rmSync, writeFileSync } from "node:fs";
+import { tmpdir } from "node:os";
+import { dirname, join, resolve } from "node:path";
+import test from "node:test";
+import { fileURLToPath } from "node:url";
+import Fastify from "fastify";
+import sensible from "@fastify/sensible";
+import { Prisma } from "@prisma/client";
+
+const serverRoot = resolve(dirname(fileURLToPath(import.meta.url)), "..");
+const databaseDir = mkdtempSync(join(tmpdir(), "sybil-workspace-search-"));
+const migration = "20261007000000_add_workspace_full_text_search";
+process.env.DATABASE_URL = `file:${join(databaseDir, "test.db")}`;
+process.env.OPENAI_API_KEY = "";
+delete process.env.ADMIN_TOKEN;
+writeFileSync(join(databaseDir, "test.db"), "");
+cpSync(join(serverRoot, "prisma/schema.prisma"), join(databaseDir, "schema.prisma"));
+for (const name of readdirSync(join(serverRoot, "prisma/migrations"))) {
+  if (name !== migration) cpSync(join(serverRoot, "prisma/migrations", name), join(databaseDir, "migrations", name), { recursive: true });
+}
+function migrate() {
+  execFileSync(process.execPath, [join(serverRoot, "node_modules/prisma/build/index.js"), "migrate", "deploy", "--schema", join(databaseDir, "schema.prisma")], {
+    cwd: serverRoot, env: process.env, stdio: "pipe",
+  });
+}
+migrate();
+const { prisma } = await import("../src/db.js");
+const oldChat = await prisma.chat.create({ data: {
+  title: "Old constellation notes",
+  messages: { create: [
+    { role: "user", content: "We photographed a nebula before the migration." },
+    { role: "system", content: "secretmigrationprompt" },
+  ] },
+} });
+const oldSearch = await prisma.search.create({ data: { query: "constellation map", answerText: "The nebula is visible." } });
+cpSync(join(serverRoot, "prisma/migrations", migration), join(databaseDir, "migrations", migration), { recursive: true });
+migrate();
+
+const { registerRoutes } = await import("../src/routes.js");
+const { workspaceSearchExpression, workspaceSearchSQL } = await import("../src/workspace-search.js");
+const app = Fastify({ logger: false });
+await app.register(sensible);
+await registerRoutes(app);
+await app.ready();
+
+async function search(query: string) {
+  const response = await app.inject({ method: "GET", url: `/v1/workspace-items?q=${encodeURIComponent(query)}` });
+  assert.equal(response.statusCode, 200, response.body);
+  return response.json();
+}
+
+test.afterEach(async () => {
+  await prisma.chat.deleteMany();
+  await prisma.search.deleteMany();
+});
+test.after(async () => {
+  await app.close();
+  await prisma.$disconnect();
+  rmSync(databaseDir, { recursive: true, force: true });
+});
+
+test("migration indexes existing titles, messages, queries, and answers", async () => {
+  assert.deepEqual(new Set((await search("nebula")).items.map((item: any) => item.id)), new Set([oldChat.id, oldSearch.id]));
+  assert.equal((await search("constellation")).items.length, 2);
+  assert.equal((await search("secretmigrationprompt")).items.length, 0);
+});
+
+test("matches full history, deduplicates messages, and excludes hidden content", async () => {
+  const chat = await prisma.chat.create({ data: {
+    title: "Travel notes", updatedAt: new Date("2000-01-01"),
+    messages: { create: [
+      { role: "user", content: "Let's discuss café planning in Zürich" },
+      { role: "assistant", content: "CAFÉ PLANNING includes booking a table" },
+      { role: "system", content: "hiddensystemvalue" },
+      { role: "tool", content: "hiddentoolvalue" },
+    ] },
+  } });
+  await prisma.chat.createMany({ data: Array.from({ length: 105 }, (_, i) => ({ title: `Recent ${i}` })) });
+  const recent = (await app.inject({ method: "GET", url: "/v1/workspace-items" })).json();
+  assert.equal(recent.items.some((item: any) => item.id === chat.id), false);
+  const result = await search("CAFE plan");
+  assert.equal(result.hasMore, false);
+  assert.deepEqual(result.items.map((item: any) => item.id), [chat.id]);
+  assert.match(result.items[0].searchSnippet, /café planning/i);
+  assert.equal(result.items[0].messages, undefined);
+  assert.equal((await search("zuri")).items.length, 1);
+  assert.equal((await search("hiddensystemvalue")).items.length, 0);
+  assert.equal((await search("hiddentoolvalue")).items.length, 0);
+});
+
+test("indexes edits, role changes, forks, rollbacks, and cascading deletes", async () => {
+  const chat = await prisma.chat.create({ data: {
+    title: "originaltitle", messages: { create: { role: "assistant", content: "originalbody" } },
+  }, include: { messages: true } });
+  const messageID = chat.messages[0].id;
+  await prisma.chat.update({ where: { id: chat.id }, data: { title: "replacementtitle" } });
+  await prisma.message.update({ where: { id: messageID }, data: { content: "replacementbody" } });
+  assert.equal((await search("original")).items.length, 0);
+  assert.equal((await search("replacementbody")).items.length, 1);
+  await prisma.message.update({ where: { id: messageID }, data: { role: "tool" } });
+  assert.equal((await search("replacementbody")).items.length, 0);
+  await prisma.message.update({ where: { id: messageID }, data: { role: "user" } });
+  assert.equal((await search("replacementbody")).items.length, 1);
+  await assert.rejects(prisma.$transaction(async (tx) => {
+    await tx.message.update({ where: { id: messageID }, data: { content: "rolledbackvalue" } });
+    throw new Error("rollback");
+  }));
+  assert.equal((await search("rolledbackvalue")).items.length, 0);
+  assert.equal((await search("replacementbody")).items.length, 1);
+  const fork = await app.inject({ method: "POST", url: `/v1/chats/${chat.id}/fork`, payload: {} });
+  assert.equal(fork.statusCode, 200, fork.body);
+  assert.equal((await search("replacementbody")).items.length, 2);
+  await prisma.message.delete({ where: { id: messageID } });
+  const onlyFork = (await search("replacementbody")).items;
+  assert.deepEqual(onlyFork.map((item: any) => item.id), [fork.json().chat.id]);
+  const starResponse = await app.inject({ method: "PATCH", url: `/v1/chats/${chat.id}/star`, payload: { starred: true } });
+  assert.equal(starResponse.statusCode, 200, starResponse.body);
+  const starredFork = (await search("replacementbody")).items[0];
+  assert.equal(starredFork.starred, true);
+  assert.ok(starredFork.starredAt);
+  assert.equal(starredFork.parentChat, undefined);
+  await prisma.chat.delete({ where: { id: chat.id } });
+  assert.equal((await search("replacement")).items.length, 0);
+  for (const table of ["ChatSearch", "MessageSearch", "SavedSearchSearch"]) {
+    await prisma.$executeRawUnsafe(`INSERT INTO "${table}" ("${table}", rank) VALUES ('integrity-check', 1)`);
+  }
+});
+
+test("saved searches match query and answer, and update/delete their index", async () => {
+  const saved = await prisma.search.create({ data: { title: "Bookmarks", query: "AI design", answerText: "Use a nebula illustration" } });
+  assert.equal((await search("ai des")).items[0].type, "search");
+  assert.match((await search("nebula")).items[0].searchSnippet, /nebula/);
+  await prisma.search.update({ where: { id: saved.id }, data: { title: "New title", query: "newquery", answerText: "newanswer" } });
+  assert.equal((await search("nebula")).items.length, 0);
+  assert.equal((await search("design")).items.length, 0);
+  assert.equal((await search("Bookmarks")).items.length, 0);
+  assert.equal((await search("newanswer")).items.length, 1);
+  await prisma.search.delete({ where: { id: saved.id } });
+  assert.equal((await search("new")).items.length, 0);
+});
+
+test("literal queries, validation, blank queries, and bounded snippets", async () => {
+  await prisma.chat.create({ data: { title: "AI OR safety", messages: { create: { role: "user", content: "longword".repeat(1000) } } } });
+  assert.equal((await search('"AI" OR safety*')).items.length, 1);
+  assert.equal((await search("AI OR other")).items.length, 0);
+  assert.equal((await search("AI")).items.length, 1);
+  assert.equal((await search("*** : () --")).items.length, 0);
+  assert.equal((await search("' UNION SELECT * FROM Chat; --")).items.length, 0);
+  assert.equal((await search("longword")).items[0].searchSnippet.length, 480);
+  const recent = (await app.inject({ method: "GET", url: "/v1/workspace-items" })).json();
+  assert.deepEqual(await search("  "), recent);
+  for (const query of ["q=" + "x".repeat(201), "q=one&q=two"]) {
+    const response = await app.inject({ method: "GET", url: `/v1/workspace-items?${query}` });
+    assert.equal(response.statusCode, 400, response.body);
+  }
+});
+
+test("caps combined results at 100 with deterministic newest-first ordering", async () => {
+  const date = new Date("2026-01-01");
+  await prisma.chat.createMany({ data: Array.from({ length: 100 }, (_, i) => ({ id: `chat-${String(i).padStart(3, "0")}`, title: "commonword", updatedAt: date })) });
+  await prisma.search.create({ data: { id: "saved", query: "commonword", updatedAt: new Date("2026-02-01") } });
+  const result = await search("common");
+  assert.equal(result.items.length, 100);
+  assert.equal(result.hasMore, true);
+  assert.equal(result.items[0].id, "saved");
+  assert.equal(result.items[1].id, "chat-000");
+  assert.equal(result.items.at(-1).id, "chat-098");
+});
+
+test("query plan uses all three FTS indexes", async () => {
+  const plan = await prisma.$queryRaw<Array<{ detail: string }>>(Prisma.sql`EXPLAIN QUERY PLAN ${workspaceSearchSQL(workspaceSearchExpression("needle")!)}`);
+  for (const table of ["ChatSearch", "MessageSearch", "SavedSearchSearch"]) {
+    assert.ok(plan.some((row) => row.detail.includes(table) && /VIRTUAL TABLE INDEX.*M\d/.test(row.detail)), plan.map((row) => row.detail).join("\n"));
+  }
+  assert.equal(plan.some((row) => row.detail.includes("CORRELATED SCALAR SUBQUERY")), false, "Excerpts must not restart FTS for each result");
+});
+
+test("vacuum preserves external-content index row identities", async () => {
+  const removed = await prisma.chat.create({ data: { title: "removed" } });
+  const kept = await prisma.chat.create({ data: { title: "kepttitle", messages: { create: { role: "user", content: "keptbody" } } } });
+  await prisma.chat.delete({ where: { id: removed.id } });
+  await prisma.$executeRaw`VACUUM`;
+  assert.equal((await search("kepttitle")).items[0].id, kept.id);
+  assert.equal((await search("kepttitle")).items[0].searchSnippet, null);
+  assert.equal((await search("keptbody")).items[0].searchSnippet, "keptbody");
+});
diff --git a/web/README.md b/web/README.md
index 6871f84..6a81dd0 100644
--- a/web/README.md
+++ b/web/README.md
@@ -34,6 +34,13 @@ Default dev URL: `http://localhost:5173`
 ## UI
 
 - Left panel: mixed list of chat conversations and Exa searches.
+- Sidebar search uses `GET /v1/workspace-items?q=…` to search all saved titles,
+  conversation messages, and web-search queries/answers. It waits 300 ms while
+  typing and cancels superseded requests. Results include a single-line matching excerpt
+  with matching words in bold and middle truncation
+  (or “Title match” for title-only chat matches), with up to 100 newest matches.
+  Clear the field or press Escape to return to recent items. Matching uses word
+  prefixes, so `plan` also finds `planning`.
 - Right panel:
   - Chat mode: transcript + provider/model controls.
   - Search mode: top AI answer block + Google-style Exa results view.
diff --git a/web/src/App.tsx b/web/src/App.tsx
index 97a02f6..7b150e7 100644
--- a/web/src/App.tsx
+++ b/web/src/App.tsx
@@ -26,6 +26,7 @@ import { ChatAttachmentList } from "@/components/chat/chat-attachment-list";
 import { ChatComposer } from "@/components/chat/chat-composer";
 import { ChatMessagesPanel } from "@/components/chat/chat-messages-panel";
 import { SearchResultsPanel } from "@/components/search/search-results-panel";
+import { SearchMatchLabel } from "@/components/search/search-match-label";
 import { SybilCharacter } from "@/components/sybil-character";
 import {
   createChat,
@@ -66,17 +67,18 @@ import {
   type WorkspaceItem,
 } from "@/lib/api";
 import { useSessionAuth } from "@/hooks/use-session-auth";
+import { useWorkspaceSearch } from "@/hooks/use-workspace-search";
 import {
   getChatModelSelection,
   getChatModelSelectionSyncKey,
 } from "@/lib/chat-model-selection";
 import {
-  filterSidebarItemsWithForkGroups,
   getForkGroupPresentation,
   groupForkedChatItems,
   shouldRequestChatTitle,
 } from "@/lib/chat-forking";
 import {
+  retainSelectedHistoryItem,
   resolveSidebarSelectionAfterRefresh,
   type SidebarSelection,
 } from "@/lib/sidebar-selection";
@@ -96,6 +98,7 @@ import { cn } from "@/lib/utils";
 type DraftSelectionKind = "chat" | "search";
 type SidebarItem = SidebarSelection & {
   title: string;
+  searchSnippet: string | null;
   parentChatId: string | null;
   updatedAt: string;
   createdAt: string;
@@ -843,6 +846,7 @@ function buildSidebarItems(items: WorkspaceItem[]): SidebarItem[] {
         kind: "chat" as const,
         id: chat.id,
         title: getChatTitle(chat),
+        searchSnippet: chat.searchSnippet ?? null,
         parentChatId: chat.parentChatId,
         updatedAt: chat.updatedAt,
         createdAt: chat.createdAt,
@@ -860,6 +864,7 @@ function buildSidebarItems(items: WorkspaceItem[]): SidebarItem[] {
       kind: "search" as const,
       id: search.id,
       title: getSearchTitle(search),
+      searchSnippet: search.searchSnippet ?? null,
       parentChatId: null,
       updatedAt: search.updatedAt,
       createdAt: search.createdAt,
@@ -1052,6 +1057,10 @@ export default function App() {
   const [contextMenu, setContextMenu] = useState<ContextMenuState | null>(null);
   const [isMobileSidebarOpen, setIsMobileSidebarOpen] = useState(false);
   const [sidebarQuery, setSidebarQuery] = useState("");
+  const [sidebarSearchRevision, setSidebarSearchRevision] = useState(0);
+  const sidebarSearch = useWorkspaceSearch(sidebarQuery, isAuthenticated, sidebarSearchRevision);
+  const isSidebarSearchActive = Boolean(sidebarQuery.trim());
+  const selectedHistoryItemRef = useRef<WorkspaceItem | null>(null);
   const initialRouteSelectionRef = useRef<SidebarSelection | null>(readSidebarSelectionFromUrl());
   const hasSyncedSelectionHistoryRef = useRef(false);
 
@@ -1117,19 +1126,16 @@ export default function App() {
   }, [pendingAttachments]);
 
   const sidebarItems = useMemo(() => buildSidebarItems(workspaceItems), [workspaceItems]);
-  const filteredSidebarItems = useMemo(() => {
-    const query = sidebarQuery.trim().toLowerCase();
-    if (!query) return groupForkedChatItems(sidebarItems).flat();
-    return filterSidebarItemsWithForkGroups(sidebarItems, (item) => {
-      const providerLabel = getProviderLabel(item.lastUsedProvider || item.initiatedProvider).toLowerCase();
-      return [item.title, item.initiatedModel, item.lastUsedModel, providerLabel]
-        .filter(Boolean)
-        .some((value) => String(value).toLowerCase().includes(query));
-    });
-  }, [sidebarItems, sidebarQuery]);
+  const searchSidebarItems = useMemo(() => buildSidebarItems(sidebarSearch.items), [sidebarSearch.items]);
+  const knownSidebarItems = useMemo(() => {
+    const matches = new Set(searchSidebarItems.map((item) => `${item.kind}:${item.id}`));
+    return [...searchSidebarItems, ...sidebarItems.filter((item) => !matches.has(`${item.kind}:${item.id}`))];
+  }, [sidebarItems, searchSidebarItems]);
   const sidebarSections = useMemo(
-    () => buildSidebarSections(filteredSidebarItems, sidebarItems),
-    [filteredSidebarItems, sidebarItems]
+    () => isSidebarSearchActive
+      ? (searchSidebarItems.length ? [{ label: "SEARCH RESULTS", items: searchSidebarItems }] : [])
+      : buildSidebarSections(sidebarItems),
+    [isSidebarSearchActive, searchSidebarItems, sidebarItems]
   );
   const orderedSidebarItems = useMemo(() => sidebarSections.flatMap((section) => section.items), [sidebarSections]);
 
@@ -1148,6 +1154,8 @@ export default function App() {
     setChats([]);
     setSearches([]);
     setWorkspaceItems([]);
+    setSidebarQuery("");
+    selectedHistoryItemRef.current = null;
     setSelectedItem(null);
     setSelectedChat(null);
     setSelectedSearch(null);
@@ -1199,6 +1207,10 @@ export default function App() {
     resetWorkspaceState();
   };
 
+  useEffect(() => {
+    if (sidebarSearch.error?.includes("bearer token")) handleAuthFailure(sidebarSearch.error);
+  }, [sidebarSearch.error]);
+
   const refreshCollections = async ({
     initialSelection,
     reportTransientError = true,
@@ -1211,12 +1223,14 @@ export default function App() {
     };
     setIsLoadingCollections(true);
     try {
-      const nextWorkspaceItems = await listWorkspaceItems();
+      let nextWorkspaceItems = await listWorkspaceItems();
       if (requestId !== collectionLoadRequestRef.current) return;
+      nextWorkspaceItems = retainSelectedHistoryItem(nextWorkspaceItems, selectedItemRef.current, selectedHistoryItemRef.current);
       const { chats: nextChats, searches: nextSearches } = splitWorkspaceItems(nextWorkspaceItems);
       setWorkspaceItems(nextWorkspaceItems);
       setChats(nextChats);
       setSearches(nextSearches);
+      setSidebarSearchRevision((current) => current + 1);
 
       setSelectedItem((current) => {
         const nextSelection = resolveSidebarSelectionAfterRefresh(current, nextWorkspaceItems, {
@@ -1512,16 +1526,16 @@ export default function App() {
   const isItemRunning = (item: SidebarSelection) =>
     item.kind === "chat" ? !!pendingChatStates[item.id] || !!activeRuns.chats[item.id] : !!runningSearchStates[item.id] || !!activeRuns.searches[item.id];
   const getChatFamilyItems = (chatId: string) => {
-    const chat = sidebarItems.find((item) => item.kind === "chat" && item.id === chatId);
+    const chat = knownSidebarItems.find((item) => item.kind === "chat" && item.id === chatId);
     if (!chat) return [];
     const rootId = chat.parentChatId ?? chat.id;
-    return sidebarItems.filter(
+    return knownSidebarItems.filter(
       (item) => item.kind === "chat" && (item.id === rootId || item.parentChatId === rootId)
     );
   };
   const isRootChat = (item: SidebarSelection) => {
     if (item.kind !== "chat") return false;
-    const chat = sidebarItems.find((candidate) => candidate.kind === "chat" && candidate.id === item.id);
+    const chat = knownSidebarItems.find((candidate) => candidate.kind === "chat" && candidate.id === item.id);
     return chat?.parentChatId === null;
   };
   const isDeleteBlocked = (item: SidebarSelection) => {
@@ -1530,9 +1544,10 @@ export default function App() {
   };
   const isSidebarTargetStarred = (item: SidebarSelection) => {
     if (item.kind === "chat") {
-      return getChatFamilyItems(item.id).find((familyItem) => familyItem.parentChatId === null)?.starred ?? false;
+      const family = getChatFamilyItems(item.id);
+      return (family.find((familyItem) => familyItem.parentChatId === null) ?? family[0])?.starred ?? false;
     }
-    return sidebarItems.find((candidate) => candidate.kind === "search" && candidate.id === item.id)?.starred ?? false;
+    return knownSidebarItems.find((candidate) => candidate.kind === "search" && candidate.id === item.id)?.starred ?? false;
   };
   const isCurrentSelection = (item: SidebarSelection) => {
     const current = selectedItemRef.current;
@@ -1928,10 +1943,21 @@ export default function App() {
         : Math.min(orderedSidebarItems.length - 1, Math.max(0, currentIndex + direction));
     const nextItem = orderedSidebarItems[nextIndex];
     const target: SidebarSelection = { kind: nextItem.kind, id: nextItem.id };
+    rememberHistoryResult(target);
     selectedItemRef.current = target;
     setSelectedItem(target);
   };
 
+  const rememberHistoryResult = (target: SidebarSelection) => {
+    const item = sidebarSearch.items.find((item) => item.type === target.kind && item.id === target.id);
+    if (!item) return;
+    selectedHistoryItemRef.current = item;
+    const { chats: matchedChats, searches: matchedSearches } = splitWorkspaceItems([item]);
+    if (matchedChats.length) setChats((current) => [...matchedChats, ...current.filter((chat) => chat.id !== item.id)]);
+    if (matchedSearches.length) setSearches((current) => [...matchedSearches, ...current.filter((search) => search.id !== item.id)]);
+    setWorkspaceItems((current) => upsertWorkspaceItem(current, item, false));
+  };
+
   useEffect(() => {
     if (!isAuthenticated) return;
 
@@ -1975,11 +2001,15 @@ export default function App() {
     if (selectedChat?.id === chatId) return getChatTitle(selectedChat, selectedChat.messages);
     const summary = chats.find((chat) => chat.id === chatId);
     if (summary) return getChatTitle(summary);
-    const sidebarItem = sidebarItems.find((item) => item.kind === "chat" && item.id === chatId);
+    const sidebarItem = knownSidebarItems.find((item) => item.kind === "chat" && item.id === chatId);
     return sidebarItem?.title ?? "New chat";
   };
 
   const applyChatSummary = (updatedChat: ChatSummary, moveToFront = true) => {
+    setSidebarSearchRevision((current) => current + 1);
+    if (selectedHistoryItemRef.current?.type === "chat" && selectedHistoryItemRef.current.id === updatedChat.id) {
+      selectedHistoryItemRef.current = chatWorkspaceItem(updatedChat);
+    }
     supersedeCollectionLoad();
     setChats((current) => {
       const withoutExisting = current.filter((chat) => chat.id !== updatedChat.id);
@@ -2012,6 +2042,10 @@ export default function App() {
   };
 
   const applySearchSummary = (updatedSearch: SearchSummary, moveToFront = true) => {
+    setSidebarSearchRevision((current) => current + 1);
+    if (selectedHistoryItemRef.current?.type === "search" && selectedHistoryItemRef.current.id === updatedSearch.id) {
+      selectedHistoryItemRef.current = searchWorkspaceItem(updatedSearch);
+    }
     supersedeCollectionLoad();
     setSearches((current) => {
       const withoutExisting = current.filter((search) => search.id !== updatedSearch.id);
@@ -2198,7 +2232,7 @@ export default function App() {
     const family = getChatFamilyItems(chatId);
     const root = family.find((item) => item.parentChatId === null) ?? family[0];
     if (!root) return;
-    applyChatSummary(await updateChatStar(root.id, !root.starred), false);
+    applyChatSummary(await updateChatStar(root.parentChatId ?? root.id, !root.starred), false);
   };
 
   const handleToggleStar = async (target: SidebarSelection) => {
@@ -2209,7 +2243,7 @@ export default function App() {
       if (target.kind === "chat") {
         await toggleChatFamilyStar(target.id);
       } else {
-        const current = sidebarItems.find((item) => item.kind === "search" && item.id === target.id);
+        const current = knownSidebarItems.find((item) => item.kind === "search" && item.id === target.id);
         const updatedSearch = await updateSearchStar(target.id, !current?.starred);
         applySearchSummary(updatedSearch, false);
       }
@@ -2301,6 +2335,11 @@ export default function App() {
       } else {
         await deleteSearch(target.id);
       }
+      const retained = selectedHistoryItemRef.current;
+      if (retained && ((retained.type === target.kind && retained.id === target.id) ||
+          (retained.type === "chat" && target.kind === "chat" && retained.parentChatId === target.id))) {
+        selectedHistoryItemRef.current = null;
+      }
       await refreshCollections({ selectFallback: true });
     } catch (err) {
       const message = err instanceof Error ? err.message : String(err);
@@ -3503,33 +3542,55 @@ export default function App() {
               <input
                 value={sidebarQuery}
                 onInput={(event) => setSidebarQuery(event.currentTarget.value)}
-                placeholder="Search chats"
-                className="h-10 w-full rounded-lg border border-violet-300/18 bg-background/66 pl-9 pr-3 text-sm text-violet-50 outline-none shadow-[inset_0_1px_0_hsl(255_100%_92%_/_0.05)] placeholder:text-muted-foreground focus:border-violet-300/45 focus:ring-1 focus:ring-ring/70"
+                placeholder="Search chats and web searches"
+                aria-label="Search conversation history and saved web searches"
+                autoComplete="off"
+                spellcheck={false}
+                onKeyDown={(event) => {
+                  if (event.key === "Escape") setSidebarQuery("");
+                }}
+                className="h-10 w-full rounded-lg border border-violet-300/18 bg-background/66 pl-9 pr-9 text-sm text-violet-50 outline-none shadow-[inset_0_1px_0_hsl(255_100%_92%_/_0.05)] placeholder:text-muted-foreground focus:border-violet-300/45 focus:ring-1 focus:ring-ring/70"
               />
+              {sidebarQuery ? (
+                <button type="button" onClick={() => setSidebarQuery("")} aria-label="Clear history search"
+                  className="absolute right-2 top-1/2 -translate-y-1/2 rounded p-1 text-violet-200/70 hover:text-violet-50">
+                  <X className="h-4 w-4" />
+                </button>
+              ) : null}
             </div>
           </div>
           <Separator className="bg-violet-300/10" />
           <div className="flex-1 overflow-y-auto px-2 py-3">
-            {isLoadingCollections && sidebarItems.length === 0 ? <p className="px-2 py-3 text-sm text-muted-foreground">Loading conversations...</p> : null}
-            {!isLoadingCollections && sidebarItems.length === 0 ? (
+            {!isSidebarSearchActive && isLoadingCollections && sidebarItems.length === 0 ? <p className="px-2 py-3 text-sm text-muted-foreground">Loading conversations...</p> : null}
+            {!isSidebarSearchActive && !isLoadingCollections && sidebarItems.length === 0 ? (
               <div className="flex h-full flex-col items-center justify-center gap-2 p-5 text-center text-sm text-muted-foreground">
                 <MessageSquare className="h-5 w-5" />
                 Start a chat or run your first search.
               </div>
             ) : null}
-            {!isLoadingCollections && sidebarItems.length > 0 && filteredSidebarItems.length === 0 ? (
-              <p className="px-2 py-3 text-sm text-muted-foreground">No chats found.</p>
+            {isSidebarSearchActive ? (
+              <div aria-live="polite" role="status">
+                {sidebarSearch.isLoading ? <p className="flex items-center gap-2 px-3 py-3 text-sm text-muted-foreground"><LoaderCircle className="h-4 w-4 animate-spin" />Searching history…</p> : null}
+                {sidebarSearch.error ? (
+                  <div className="space-y-2 px-3 py-3 text-sm">
+                    <p className="text-red-300">{sidebarSearch.error}</p>
+                    <Button variant="secondary" onClick={() => setSidebarSearchRevision((current) => current + 1)}>Try again</Button>
+                  </div>
+                ) : !sidebarSearch.isLoading && searchSidebarItems.length === 0 ? (
+                  <p className="px-3 py-3 text-sm text-muted-foreground">No matching chats or web searches. Try a title, query, or words from a conversation.</p>
+                ) : null}
+              </div>
             ) : null}
             {sidebarSections.map((section) => (
               <div key={section.label} className="mb-4">
                 <p className="px-3 pb-2 text-[11px] font-semibold text-violet-200/48">{section.label}</p>
                 {section.items.map((item) => {
                   const active = selectedItem?.kind === item.kind && selectedItem.id === item.id;
-                  const isForkChild = item.kind === "chat" && item.parentChatId !== null;
-                  const familyItems = item.kind === "chat" ? getChatFamilyItems(item.id) : [item];
+                  const isForkChild = !isSidebarSearchActive && item.kind === "chat" && item.parentChatId !== null;
+                  const familyItems = !isSidebarSearchActive && item.kind === "chat" ? getChatFamilyItems(item.id) : [item];
                   const itemIsRunning = familyItems.some((familyItem) => isItemRunning(familyItem));
                   const itemIsStarred =
-                    familyItems.find((familyItem) => familyItem.parentChatId === null)?.starred ?? false;
+                    familyItems.find((familyItem) => familyItem.parentChatId === null)?.starred ?? item.starred;
                   const itemUpdatedAt = familyItems.reduce(
                     (newest, familyItem) =>
                       new Date(familyItem.updatedAt).getTime() > new Date(newest).getTime()
@@ -3555,6 +3616,7 @@ export default function App() {
                         draftKindRef.current = null;
                         setDraftKind(null);
                         const target = { kind: item.kind, id: item.id } as SidebarSelection;
+                        rememberHistoryResult(target);
                         selectedItemRef.current = target;
                         setSelectedItem(target);
                         setIsMobileSidebarOpen(false);
@@ -3573,7 +3635,7 @@ export default function App() {
                               active ? "border-cyan-200/35 bg-cyan-300/12 text-cyan-100" : "border-violet-300/18 text-violet-200/70"
                             )}
                           >
-                            {item.kind === "chat" ? <MessageSquare className="h-3.5 w-3.5" /> : <Search className="h-3.5 w-3.5" />}
+                            {item.kind === "chat" ? (item.parentChatId ? <GitFork className="h-3.5 w-3.5" aria-label="Fork" /> : <MessageSquare className="h-3.5 w-3.5" />) : <Search className="h-3.5 w-3.5" />}
                           </span>
                           <span className="flex min-w-0 flex-1 items-center gap-1.5">
                             <span className="truncate text-sm font-semibold">{item.title}</span>
@@ -3598,6 +3660,9 @@ export default function App() {
                               </span>
                             ) : null}
                           </span>
+                          {isSidebarSearchActive ? (
+                            <SearchMatchLabel text={item.searchSnippet || "Title match"} query={item.searchSnippet ? sidebarQuery : ""} />
+                          ) : null}
                         </div>
                       )}
                     </button>
@@ -3605,6 +3670,9 @@ export default function App() {
                 })}
               </div>
             ))}
+            {isSidebarSearchActive && sidebarSearch.hasMore ? (
+              <p className="px-3 py-2 text-xs text-muted-foreground">Showing the 100 most recent matches. Refine your search to find more.</p>
+            ) : null}
           </div>
         </aside>
 
diff --git a/web/src/components/search/search-match-label.tsx b/web/src/components/search/search-match-label.tsx
new file mode 100644
index 0000000..fee0b75
--- /dev/null
+++ b/web/src/components/search/search-match-label.tsx
@@ -0,0 +1,96 @@
+/// <reference lib="es2022.intl" />
+import { useLayoutEffect, useMemo, useRef, useState } from "preact/hooks";
+
+const words = /[\p{L}\p{N}\p{M}\p{Co}]+/gu;
+const fold = (text: string) => text.normalize("NFD").replace(/\p{M}/gu, "").toLowerCase();
+const graphemes = new Intl.Segmenter(undefined, { granularity: "grapheme" });
+
+export function SearchMatchLabel({ text: source, query }: { text: string; query: string }) {
+  const text = source.replace(/\s+/gu, " ").trim();
+  const containerRef = useRef<HTMLSpanElement>(null);
+  const measureRef = useRef<HTMLSpanElement>(null);
+  const ellipsisRef = useRef<HTMLSpanElement>(null);
+  const [kept, setKept] = useState<number | null>(null);
+  const boundaries = useMemo(() => [0, ...Array.from(graphemes.segment(text), ({ index, segment }) => index + segment.length)], [text]);
+  const runs = useMemo(() => {
+    const terms = (query.match(words) ?? []).map(fold).filter(Boolean);
+    const result: Array<{ start: number; end: number; match: boolean }> = [];
+    let cursor = 0;
+    for (const word of text.matchAll(words)) {
+      if (word.index > cursor) result.push({ start: cursor, end: word.index, match: false });
+      cursor = word.index + word[0].length;
+      result.push({ start: word.index, end: cursor, match: terms.some((term) => fold(word[0]).startsWith(term)) });
+    }
+    if (cursor < text.length) result.push({ start: cursor, end: text.length, match: false });
+    return result;
+  }, [text, query]);
+
+  const renderRange = (start: number, end: number) => runs.flatMap((run) => {
+    const value = text.slice(Math.max(start, run.start), Math.min(end, run.end));
+    if (run.end <= start || run.start >= end) return [];
+    return [run.match
+      ? <strong key={`${start}:${run.start}`} className="font-semibold text-violet-100/95">{value}</strong>
+      : <span key={`${start}:${run.start}`}>{value}</span>];
+  });
+
+  useLayoutEffect(() => {
+    const container = containerRef.current;
+    const measure = measureRef.current;
+    const ellipsis = ellipsisRef.current;
+    if (!container || !measure || !ellipsis) return;
+    let disposed = false;
+    const update = () => {
+      if (disposed) return;
+      const width = container.getBoundingClientRect().width;
+      if (measure.getBoundingClientRect().width <= width) { setKept(null); return; }
+      // Measure the styled DOM, including bold runs, instead of guessing a
+      // character limit. Grapheme boundaries keep accents and emoji intact.
+      const nodes = Array.from(measure.children, (child) => child.firstChild as Text);
+      const range = document.createRange();
+      const measureRange = (start: number, end: number) => {
+        if (start >= end) return 0;
+        let offset = 0;
+        let started = false;
+        for (const node of nodes) {
+          const next = offset + node.length;
+          if (!started && start <= next) { range.setStart(node, start - offset); started = true; }
+          if (end <= next) { range.setEnd(node, end - offset); break; }
+          offset = next;
+        }
+        return range.getBoundingClientRect().width;
+      };
+      const count = boundaries.length - 1;
+      const ellipsisWidth = ellipsis.getBoundingClientRect().width;
+      let low = 0;
+      let high = count - 1;
+      while (low < high) {
+        const middle = Math.ceil((low + high) / 2);
+        const prefix = boundaries[Math.ceil(middle / 2)];
+        const suffix = boundaries[count - Math.floor(middle / 2)];
+        if (measureRange(0, prefix) + ellipsisWidth + measureRange(suffix, text.length) <= width - 1) low = middle;
+        else high = middle - 1;
+      }
+      setKept(low);
+    };
+    update();
+    const observer = new ResizeObserver(update);
+    observer.observe(container);
+    void document.fonts.ready.then(update);
+    document.fonts.addEventListener("loadingdone", update);
+    return () => { disposed = true; observer.disconnect(); document.fonts.removeEventListener("loadingdone", update); };
+  }, [text, runs, boundaries]);
+
+  const count = boundaries.length - 1;
+  const truncated = kept !== null && kept < count;
+  return (
+    <span ref={containerRef} title={text} className="relative col-start-2 block min-w-0 overflow-hidden whitespace-nowrap text-xs leading-5 text-secondary-foreground/75">
+      <span className="sr-only">{text}</span>
+      <span aria-hidden="true">
+        {truncated ? <>{renderRange(0, boundaries[Math.ceil(kept / 2)])}…{renderRange(boundaries[count - Math.floor(kept / 2)], text.length)}</> : renderRange(0, text.length)}
+      </span>
+      <span aria-hidden="true" className="pointer-events-none invisible absolute left-0 top-0 whitespace-pre">
+        <span ref={measureRef}>{renderRange(0, text.length)}</span><span ref={ellipsisRef}>…</span>
+      </span>
+    </span>
+  );
+}
diff --git a/web/src/hooks/use-workspace-search.ts b/web/src/hooks/use-workspace-search.ts
new file mode 100644
index 0000000..e71405c
--- /dev/null
+++ b/web/src/hooks/use-workspace-search.ts
@@ -0,0 +1,30 @@
+import { useEffect, useState } from "preact/hooks";
+import { searchWorkspaceItems, type WorkspaceItem, type WorkspaceSearchResponse } from "@/lib/api";
+import { scheduleWorkspaceSearch } from "@/lib/workspace-search";
+
+type SearchState = WorkspaceSearchResponse & { query: string; revision: number; error: string | null };
+const EMPTY_ITEMS: WorkspaceItem[] = [];
+
+export function useWorkspaceSearch(query: string, enabled: boolean, revision: number) {
+  const trimmed = query.trim();
+  const [state, setState] = useState<SearchState | null>(null);
+  const validationError = trimmed.length > 200 ? "Use 200 characters or fewer." : null;
+
+  useEffect(() => {
+    setState(null);
+    if (!enabled || !trimmed || validationError) return;
+    return scheduleWorkspaceSearch(trimmed, searchWorkspaceItems,
+      (result) => setState({ ...result, query: trimmed, revision, error: null }),
+      (error) => setState({ items: [], hasMore: false, query: trimmed, revision, error: error instanceof Error ? error.message : String(error) })
+    );
+  }, [trimmed, enabled, revision, validationError]);
+
+  // Hide obsolete results immediately, even before effect cleanup runs.
+  const current = enabled && state?.query === trimmed && state.revision === revision ? state : null;
+  return {
+    items: current?.items ?? EMPTY_ITEMS,
+    hasMore: current?.hasMore ?? false,
+    error: validationError ?? current?.error ?? null,
+    isLoading: enabled && Boolean(trimmed) && !validationError && !current,
+  };
+}
diff --git a/web/src/lib/api.ts b/web/src/lib/api.ts
index 95cddd4..def398f 100644
--- a/web/src/lib/api.ts
+++ b/web/src/lib/api.ts
@@ -33,7 +33,9 @@ export type SearchWorkspaceItem = SearchSummary & {
   type: "search";
 };
 
-export type WorkspaceItem = ChatWorkspaceItem | SearchWorkspaceItem;
+export type WorkspaceItem = (ChatWorkspaceItem | SearchWorkspaceItem) & { searchSnippet?: string | null };
+
+export type WorkspaceSearchResponse = { items: WorkspaceItem[]; hasMore: boolean };
 
 export type Message = {
   id: string;
@@ -272,6 +274,10 @@ export async function listWorkspaceItems() {
   return data.items;
 }
 
+export function searchWorkspaceItems(query: string, signal?: AbortSignal) {
+  return api<WorkspaceSearchResponse>(`/v1/workspace-items?${new URLSearchParams({ q: query })}`, { signal });
+}
+
 export async function verifySession() {
   return api<{ authenticated: true; mode: "open" | "token" }>("/v1/auth/session");
 }
diff --git a/web/src/lib/sidebar-selection.ts b/web/src/lib/sidebar-selection.ts
index a3aee2a..d2573ca 100644
--- a/web/src/lib/sidebar-selection.ts
+++ b/web/src/lib/sidebar-selection.ts
@@ -2,6 +2,16 @@ export type SidebarSelection = { kind: "chat" | "search"; id: string };
 
 type WorkspaceSelectionItem = { type: SidebarSelection["kind"]; id: string };
 
+export function retainSelectedHistoryItem<T extends WorkspaceSelectionItem>(
+  items: T[], selection: SidebarSelection | null, retained: T | null
+): T[] {
+  if (retained && selection?.kind === retained.type && selection.id === retained.id &&
+      !items.some((item) => item.type === retained.type && item.id === retained.id)) {
+    return [...items, retained];
+  }
+  return items;
+}
+
 type ResolveSidebarSelectionOptions = {
   initialSelection?: SidebarSelection;
   selectFallback?: boolean;
diff --git a/web/src/lib/workspace-search.ts b/web/src/lib/workspace-search.ts
new file mode 100644
index 0000000..3077b88
--- /dev/null
+++ b/web/src/lib/workspace-search.ts
@@ -0,0 +1,24 @@
+import type { WorkspaceSearchResponse } from "./api";
+
+// Cleanup cancels both the debounce and fetch, and also rejects late responses
+// from transports that finish after cancellation.
+export function scheduleWorkspaceSearch(
+  query: string,
+  request: (query: string, signal: AbortSignal) => Promise<WorkspaceSearchResponse>,
+  onResult: (result: WorkspaceSearchResponse) => void,
+  onError: (error: unknown) => void
+) {
+  const controller = new AbortController();
+  const timer = setTimeout(async () => {
+    try {
+      const result = await request(query, controller.signal);
+      if (!controller.signal.aborted) onResult(result);
+    } catch (error) {
+      if (!controller.signal.aborted) onError(error);
+    }
+  }, 300);
+  return () => {
+    clearTimeout(timer);
+    controller.abort();
+  };
+}
diff --git a/web/tests/workspace-search.test.mjs b/web/tests/workspace-search.test.mjs
new file mode 100644
index 0000000..8ca272f
--- /dev/null
+++ b/web/tests/workspace-search.test.mjs
@@ -0,0 +1,80 @@
+import assert from "node:assert/strict";
+import test from "node:test";
+import { scheduleWorkspaceSearch } from "../src/lib/workspace-search.ts";
+import { retainSelectedHistoryItem, resolveSidebarSelectionAfterRefresh } from "../src/lib/sidebar-selection.ts";
+
+const flush = async () => { await Promise.resolve(); await Promise.resolve(); };
+
+test("typing is debounced and superseded requests never start", async (t) => {
+  t.mock.timers.enable({ apis: ["setTimeout"] });
+  const queries = [];
+  const results = [];
+  const request = async (query) => { queries.push(query); return { items: [], hasMore: false }; };
+  const reportError = (error) => assert.fail(String(error));
+  const cancelFirst = scheduleWorkspaceSearch("ne", request, (result) => results.push(result), reportError);
+  t.mock.timers.tick(299);
+  assert.deepEqual(queries, []);
+  cancelFirst();
+  const cancelLast = scheduleWorkspaceSearch("nebula", request, (result) => results.push(result), reportError);
+  t.mock.timers.tick(300);
+  await flush();
+  assert.deepEqual(queries, ["nebula"]);
+  assert.deepEqual(results, [{ items: [], hasMore: false }]);
+  cancelLast();
+});
+
+test("cancellation aborts the transport and discards stale results and errors", async (t) => {
+  t.mock.timers.enable({ apis: ["setTimeout"] });
+  let resolveFirst;
+  let rejectSecond;
+  let signal;
+  const results = [];
+  const errors = [];
+  const first = scheduleWorkspaceSearch("first", (_query, value) => {
+    signal = value;
+    return new Promise((resolve) => { resolveFirst = resolve; });
+  }, (result) => results.push(result), (error) => errors.push(error));
+  t.mock.timers.tick(300);
+  first();
+  assert.equal(signal.aborted, true);
+  const second = scheduleWorkspaceSearch("second", () => new Promise((_resolve, reject) => { rejectSecond = reject; }),
+    (result) => results.push(result), (error) => errors.push(error));
+  t.mock.timers.tick(300);
+  second();
+  resolveFirst({ items: [{ id: "stale" }], hasMore: true });
+  rejectSecond(new Error("stale failure"));
+  await flush();
+  assert.deepEqual(results, []);
+  assert.deepEqual(errors, []);
+});
+
+test("search results retain excerpts and truncation info; failures reach the UI", async (t) => {
+  t.mock.timers.enable({ apis: ["setTimeout"] });
+  const expected = { items: [{ type: "chat", id: "old", searchSnippet: "A nebula in the sky" }], hasMore: true };
+  let received;
+  let error;
+  const cancel = scheduleWorkspaceSearch("nebula", async () => expected, (result) => { received = result; }, assert.fail);
+  t.mock.timers.tick(300);
+  await flush();
+  assert.deepEqual(received, expected);
+  cancel();
+  const cancelFailure = scheduleWorkspaceSearch("nebula", async () => { throw new Error("Offline"); }, assert.fail, (result) => { error = result; });
+  t.mock.timers.tick(300);
+  await flush();
+  assert.equal(error.message, "Offline");
+  cancelFailure();
+});
+
+test("opening older chat/search results survives collection refresh without restoring deleted or unrelated items", () => {
+  const recent = [{ type: "chat", id: "recent" }];
+  for (const kind of ["chat", "search"]) {
+    const selection = { kind, id: "old" };
+    const retained = { type: kind, id: "old" };
+    const refreshed = retainSelectedHistoryItem(recent, selection, retained);
+    assert.deepEqual(resolveSidebarSelectionAfterRefresh(selection, refreshed), selection);
+    assert.equal(retainSelectedHistoryItem(refreshed, selection, retained), refreshed);
+    assert.equal(retainSelectedHistoryItem(recent, { kind, id: "different" }, retained), recent);
+    assert.equal(retainSelectedHistoryItem(recent, selection, null), recent);
+    assert.equal(retainSelectedHistoryItem(recent, null, retained), recent);
+  }
+});