diff --git a/apps/macos-sync/Sources/CairnquireSync/API/Client.swift b/apps/macos-sync/Sources/CairnquireSync/API/Client.swift
index 4df1756..f871032 100644
--- a/apps/macos-sync/Sources/CairnquireSync/API/Client.swift
+++ b/apps/macos-sync/Sources/CairnquireSync/API/Client.swift
@@ -209,6 +209,24 @@ public actor APIClient {
         
         return try await perform(request)
     }
+
+    public func searchDocuments(query: String) async throws -> [SearchResult] {
+        var components = URLComponents(url: baseURL.appendingPathComponent("api/search"), resolvingAgainstBaseURL: false)
+        components?.queryItems = [URLQueryItem(name: "q", value: query)]
+
+        guard let url = components?.url else {
+            throw APIError(error: "invalid search URL")
+        }
+
+        var request = URLRequest(url: url)
+        if let token = apiToken {
+            request.setValue("Bearer \(token)", forHTTPHeaderField: "Authorization")
+        }
+        request.setValue("application/json", forHTTPHeaderField: "Accept")
+
+        let response: SearchResponse = try await perform(request)
+        return response.results
+    }
     
     // MARK: - Sync
     
diff --git a/apps/macos-sync/Sources/CairnquireSync/API/Models.swift b/apps/macos-sync/Sources/CairnquireSync/API/Models.swift
index 7c816e8..1fbcdd5 100644
--- a/apps/macos-sync/Sources/CairnquireSync/API/Models.swift
+++ b/apps/macos-sync/Sources/CairnquireSync/API/Models.swift
@@ -52,6 +52,12 @@ public struct DocumentSaveResponse: Codable {
     public let hash: String
 }
 
+public struct SearchResult: Codable, Identifiable {
+    public var id: String { path }
+    public let path: String
+    public let title: String
+}
+
 public struct SyncInitRequest: Codable {
     public let deviceId: String
     public let rootPath: String
@@ -178,6 +184,10 @@ public struct DocumentsListResponse: Codable {
     public let documents: [DocumentRecord]
 }
 
+public struct SearchResponse: Codable {
+    public let results: [SearchResult]
+}
+
 public enum UploadDuplicateAction: String {
     case overwrite
     case rename
diff --git a/apps/macos-sync/Sources/CairnquireSync/UI/MenuBarController.swift b/apps/macos-sync/Sources/CairnquireSync/UI/MenuBarController.swift
index 03f1f47..a57e0ee 100644
--- a/apps/macos-sync/Sources/CairnquireSync/UI/MenuBarController.swift
+++ b/apps/macos-sync/Sources/CairnquireSync/UI/MenuBarController.swift
@@ -18,6 +18,11 @@ public class MenuBarController: NSObject, ObservableObject, NSWindowDelegate {
     @Published public private(set) var isLoadingRecentUploads = false
     @Published public private(set) var recentUploadsError: String?
     @Published public private(set) var clipboardNotice: ClipboardNotice?
+    @Published public var searchQuery = ""
+    @Published public private(set) var searchResults: [SearchResult] = []
+    @Published public private(set) var isSearching = false
+    @Published public private(set) var searchError: String?
+    @Published public var selectedSearchIndex = 0
     
     public var cancellables = Set<AnyCancellable>()
     
@@ -27,6 +32,7 @@ public class MenuBarController: NSObject, ObservableObject, NSWindowDelegate {
     private var uploadManager: UploadManager
     private var folderWatcher: FolderWatcher?
     private var syncTimer: Timer?
+    private var searchTask: Task<Void, Never>?
     
     private var settingsWindow: NSWindow?
     private var uploadsWindow: NSWindow?
@@ -59,6 +65,7 @@ public class MenuBarController: NSObject, ObservableObject, NSWindowDelegate {
                 apiClient = APIClient(baseURL: url, apiToken: newConfig.apiToken)
                 uploadManager = UploadManager(client: apiClient, config: newConfig)
                 syncEngine = SyncEngine(client: apiClient, config: newConfig)
+                resetSearch()
                 await refreshRecentUploads()
                 await setupSync()
             }
@@ -308,6 +315,100 @@ public class MenuBarController: NSObject, ObservableObject, NSWindowDelegate {
             recentUploadsError = error.localizedDescription
         }
     }
+
+    public func updateSearchQuery(_ query: String) {
+        searchQuery = query
+        selectedSearchIndex = 0
+        searchTask?.cancel()
+
+        let trimmed = query.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !trimmed.isEmpty else {
+            searchResults = []
+            isSearching = false
+            searchError = nil
+            return
+        }
+
+        isSearching = true
+        searchError = nil
+        searchTask = Task { [weak self] in
+            do {
+                try await Task.sleep(for: .milliseconds(180))
+                await self?.performSearch(for: trimmed)
+            } catch {
+                await MainActor.run {
+                    if self?.searchQuery.trimmingCharacters(in: .whitespacesAndNewlines) == trimmed {
+                        self?.isSearching = false
+                    }
+                }
+            }
+        }
+    }
+
+    public func clearSearch() {
+        resetSearch()
+    }
+
+    public func moveSearchSelection(by delta: Int) {
+        guard !searchResults.isEmpty else { return }
+        selectedSearchIndex = min(max(selectedSearchIndex + delta, 0), searchResults.count - 1)
+    }
+
+    public func openSelectedSearchResult() {
+        guard searchResults.indices.contains(selectedSearchIndex) else { return }
+        openSearchResult(searchResults[selectedSearchIndex])
+    }
+
+    public func openSearchResult(_ result: SearchResult) {
+        guard let url = documentURL(for: result) else { return }
+        NSWorkspace.shared.open(url)
+    }
+
+    private func performSearch(for query: String) async {
+        do {
+            let results = try await apiClient.searchDocuments(query: liveSearchQuery(for: query))
+            guard !Task.isCancelled else { return }
+            guard searchQuery.trimmingCharacters(in: .whitespacesAndNewlines) == query else { return }
+            searchResults = Array(results.prefix(8))
+            selectedSearchIndex = min(selectedSearchIndex, max(searchResults.count - 1, 0))
+            searchError = nil
+        } catch {
+            guard !Task.isCancelled else { return }
+            searchResults = []
+            searchError = error.localizedDescription
+        }
+        isSearching = false
+    }
+
+    private func resetSearch() {
+        searchTask?.cancel()
+        searchQuery = ""
+        searchResults = []
+        isSearching = false
+        searchError = nil
+        selectedSearchIndex = 0
+    }
+
+    private func liveSearchQuery(for query: String) -> String {
+        let terms = query
+            .components(separatedBy: CharacterSet.alphanumerics.inverted)
+            .map { $0.trimmingCharacters(in: .whitespacesAndNewlines) }
+            .filter { !$0.isEmpty }
+
+        guard !terms.isEmpty else { return query }
+        return terms.map { "\($0)*" }.joined(separator: " ")
+    }
+
+    private func documentURL(for result: SearchResult) -> URL? {
+        guard let baseURL = config.serverBaseURL else { return nil }
+        let trimmedPath = result.path.hasSuffix(".md") ? String(result.path.dropLast(3)) : result.path
+        var allowed = CharacterSet.urlPathAllowed
+        allowed.remove(charactersIn: "?#")
+        guard let encodedPath = trimmedPath.addingPercentEncoding(withAllowedCharacters: allowed) else {
+            return nil
+        }
+        return URL(string: "docs/\(encodedPath)", relativeTo: baseURL)?.absoluteURL
+    }
     
     public func createNote() {
         switch config.effectiveNewNoteAction {
diff --git a/apps/macos-sync/Sources/CairnquireSync/UI/StatusPopoverView.swift b/apps/macos-sync/Sources/CairnquireSync/UI/StatusPopoverView.swift
index 667e007..9830415 100644
--- a/apps/macos-sync/Sources/CairnquireSync/UI/StatusPopoverView.swift
+++ b/apps/macos-sync/Sources/CairnquireSync/UI/StatusPopoverView.swift
@@ -2,6 +2,7 @@ import SwiftUI
 
 public struct StatusPopoverView: View {
     @ObservedObject public var controller: MenuBarController
+    @FocusState private var searchFocused: Bool
     
     public init(controller: MenuBarController) {
         self.controller = controller
@@ -12,6 +13,10 @@ public struct StatusPopoverView: View {
             // Header with status
             headerSection
             
+            Divider()
+
+            searchSection
+
             Divider()
             
             // Quick actions
@@ -27,8 +32,23 @@ public struct StatusPopoverView: View {
             // Footer
             footerSection
         }
-        .frame(width: 320)
+        .frame(width: 360)
         .padding(.vertical, 12)
+        .onAppear {
+            Task { @MainActor in
+                searchFocused = true
+            }
+        }
+        .onMoveCommand { direction in
+            switch direction {
+            case .up:
+                controller.moveSearchSelection(by: -1)
+            case .down:
+                controller.moveSearchSelection(by: 1)
+            default:
+                break
+            }
+        }
     }
     
     // MARK: - Sections
@@ -130,6 +150,75 @@ public struct StatusPopoverView: View {
         .padding(.horizontal, 16)
         .padding(.vertical, 12)
     }
+
+    @ViewBuilder
+    private var searchSection: some View {
+        VStack(alignment: .leading, spacing: 8) {
+            HStack(spacing: 8) {
+                Image(systemName: "magnifyingglass")
+                    .font(.system(size: 13, weight: .medium))
+                    .foregroundColor(.secondary)
+
+                TextField(
+                    "Search documents",
+                    text: Binding(
+                        get: { controller.searchQuery },
+                        set: { controller.updateSearchQuery($0) }
+                    )
+                )
+                .textFieldStyle(.plain)
+                .focused($searchFocused)
+                .onSubmit {
+                    controller.openSelectedSearchResult()
+                }
+
+                if controller.isSearching {
+                    ProgressView()
+                        .controlSize(.small)
+                        .scaleEffect(0.65)
+                        .frame(width: 14, height: 14)
+                }
+            }
+            .padding(.horizontal, 10)
+            .padding(.vertical, 8)
+            .background(Color(NSColor.controlBackgroundColor))
+            .clipShape(RoundedRectangle(cornerRadius: 8))
+
+            if !controller.searchQuery.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty {
+                searchResultsList
+            }
+        }
+        .padding(.horizontal, 16)
+        .padding(.vertical, 10)
+    }
+
+    @ViewBuilder
+    private var searchResultsList: some View {
+        if controller.searchResults.isEmpty {
+            Text(controller.isSearching ? "Searching..." : (controller.searchError == nil ? "No results" : "Search unavailable"))
+                .font(.caption)
+                .foregroundColor(.secondary)
+                .frame(maxWidth: .infinity, alignment: .center)
+                .padding(.vertical, 8)
+        } else {
+            VStack(spacing: 2) {
+                ForEach(Array(controller.searchResults.enumerated()), id: \.element.id) { index, result in
+                    SearchResultRow(
+                        result: result,
+                        isSelected: index == controller.selectedSearchIndex
+                    ) {
+                        controller.selectedSearchIndex = index
+                        controller.openSearchResult(result)
+                    }
+                    .onHover { isHovered in
+                        if isHovered {
+                            controller.selectedSearchIndex = index
+                        }
+                    }
+                }
+            }
+        }
+    }
     
     @ViewBuilder
     private var recentUploadsSection: some View {
@@ -272,6 +361,47 @@ private struct RecentUploadRow: View {
     }
 }
 
+private struct SearchResultRow: View {
+    let result: SearchResult
+    let isSelected: Bool
+    let action: () -> Void
+
+    var body: some View {
+        Button(action: action) {
+            HStack(spacing: 8) {
+                Image(systemName: "doc.text")
+                    .font(.system(size: 14, weight: .medium))
+                    .foregroundColor(isSelected ? .white : .accentColor)
+                    .frame(width: 18)
+
+                VStack(alignment: .leading, spacing: 2) {
+                    Text(result.title.isEmpty ? result.path : result.title)
+                        .font(.caption)
+                        .foregroundColor(isSelected ? .white : .primary)
+                        .lineLimit(1)
+                    Text(result.path)
+                        .font(.caption2)
+                        .foregroundColor(isSelected ? .white.opacity(0.82) : .secondary)
+                        .lineLimit(1)
+                }
+
+                Spacer(minLength: 0)
+
+                Image(systemName: "return")
+                    .font(.caption2)
+                    .foregroundColor(isSelected ? .white.opacity(0.75) : .secondary)
+                    .opacity(isSelected ? 1 : 0)
+            }
+            .padding(.horizontal, 8)
+            .padding(.vertical, 6)
+            .frame(height: 44)
+            .background(isSelected ? Color.accentColor : Color.clear)
+            .clipShape(RoundedRectangle(cornerRadius: 6))
+        }
+        .buttonStyle(.plain)
+    }
+}
+
 // MARK: - Action Button
 
 struct ActionButton: View {
diff --git a/apps/macos-sync/Sources/CairnquireSyncApp/App.swift b/apps/macos-sync/Sources/CairnquireSyncApp/App.swift
index acd6b8f..3c887cf 100644
--- a/apps/macos-sync/Sources/CairnquireSyncApp/App.swift
+++ b/apps/macos-sync/Sources/CairnquireSyncApp/App.swift
@@ -223,8 +223,10 @@ class AppDelegate: NSObject, NSApplicationDelegate {
     private func showPopover() {
         guard let button = dropButton else { return }
         Task { @MainActor in
+            controller.clearSearch()
             await controller.refreshRecentUploads()
         }
+        NSApp.activate(ignoringOtherApps: true)
         popover.show(relativeTo: button.bounds, of: button, preferredEdge: .minY)
         
         NSEvent.addGlobalMonitorForEvents(matching: [.leftMouseDown, .rightMouseDown]) { [weak self] event in