diff --git a/Outpost/Features/Search/DocumentTitleSearchViewModel.swift b/Outpost/Features/Search/DocumentTitleSearchViewModel.swift
new file mode 100644
index 0000000..15da66f
--- /dev/null
+++ b/Outpost/Features/Search/DocumentTitleSearchViewModel.swift
@@ -0,0 +1,48 @@
+import Foundation
+import Observation
+import OutlineKit
+
+/// Backs the contextual toolbar search — matches scoped to whichever collection
+/// is currently open ("search what you're looking at").
+///
+/// Uses `documents.search` rather than `documents.search_titles`: the latter
+/// consistently failed against the connected server (likely unavailable on
+/// this Outline version — see ARCHITECTURE.md's note on server version drift),
+/// while `documents.search` is the same, longer-established endpoint the
+/// sidebar's global search already relies on.
+@MainActor
+@Observable
+final class DocumentTitleSearchViewModel {
+    var results: [OutlineDocumentSearchResult] = []
+    var isSearching = false
+    var errorMessage: String?
+
+    private let apiClient: OutlineAPIClient
+    private let collectionId: String
+
+    init(apiClient: OutlineAPIClient, collectionId: String) {
+        self.apiClient = apiClient
+        self.collectionId = collectionId
+    }
+
+    func search(query: String) async {
+        let trimmed = query.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !trimmed.isEmpty else {
+            results = []
+            errorMessage = nil
+            return
+        }
+
+        isSearching = true
+        errorMessage = nil
+        defer { isSearching = false }
+
+        do {
+            results = try await apiClient.searchDocuments(
+                DocumentSearchRequest(query: trimmed, collectionId: collectionId)
+            )
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Search failed. Try again.")
+        }
+    }
+}
diff --git a/Outpost/Features/Search/GlobalSearchResultsView.swift b/Outpost/Features/Search/GlobalSearchResultsView.swift
new file mode 100644
index 0000000..790e0a7
--- /dev/null
+++ b/Outpost/Features/Search/GlobalSearchResultsView.swift
@@ -0,0 +1,136 @@
+#if os(macOS)
+import SwiftUI
+import OutlineKit
+
+struct GlobalSearchResultsView: View {
+    @State private var viewModel: GlobalSearchViewModel
+    let query: String
+
+    init(apiClient: OutlineAPIClient, query: String) {
+        _viewModel = State(initialValue: GlobalSearchViewModel(apiClient: apiClient))
+        self.query = query
+    }
+
+    private var searchKey: String {
+        [
+            query,
+            viewModel.collectionFilter?.id ?? "",
+            viewModel.dateFilter?.rawValue ?? "",
+            viewModel.sort.rawValue,
+            viewModel.direction.rawValue,
+            viewModel.statusFilter.map(\.rawValue).sorted().joined(separator: ",")
+        ].joined(separator: "|")
+    }
+
+    var body: some View {
+        // No `.navigationTitle` — `ContentView_macOS`'s leading toolbar item
+        // already shows a "Search" pill while global search is active.
+        results
+            .toolbar {
+                ToolbarItemGroup(placement: .primaryAction) {
+                    collectionPicker
+                    sortPicker
+                    dateFilterPicker
+                    statusFilterMenu
+                }
+            }
+            .task { await viewModel.loadCollectionsIfNeeded() }
+            .task(id: searchKey) {
+                try? await Task.sleep(for: .milliseconds(300))
+                guard !Task.isCancelled else { return }
+                await viewModel.search(query: query)
+            }
+    }
+
+    // `documents.search`'s `collectionId` is a single UUID, not an array — this
+    // stays single-select because that's genuinely all the endpoint supports,
+    // not an arbitrary UI limitation.
+    private var collectionPicker: some View {
+        Picker("Collection", selection: $viewModel.collectionFilter) {
+            Text("All Collections").tag(OutlineCollection?.none)
+            ForEach(viewModel.availableCollections) { collection in
+                Text(collection.name).tag(Optional(collection))
+            }
+        }
+        .padding(.horizontal, 4)
+    }
+
+    private var sortPicker: some View {
+        Picker("Sort", selection: $viewModel.sort) {
+            Text("Relevance").tag(DocumentSearchSort.relevance)
+            Text("Updated").tag(DocumentSearchSort.updatedAt)
+            Text("Created").tag(DocumentSearchSort.createdAt)
+            Text("Title").tag(DocumentSearchSort.title)
+        }
+        .padding(.horizontal, 4)
+    }
+
+    private var dateFilterPicker: some View {
+        Picker("Date", selection: $viewModel.dateFilter) {
+            Text("Any Time").tag(DocumentSearchDateFilter?.none)
+            Text("Past Day").tag(Optional(DocumentSearchDateFilter.day))
+            Text("Past Week").tag(Optional(DocumentSearchDateFilter.week))
+            Text("Past Month").tag(Optional(DocumentSearchDateFilter.month))
+            Text("Past Year").tag(Optional(DocumentSearchDateFilter.year))
+        }
+        .padding(.horizontal, 4)
+    }
+
+    private var statusFilterMenu: some View {
+        Menu {
+            ForEach(DocumentStatusFilter.allCases, id: \.self) { status in
+                Button {
+                    if viewModel.statusFilter.contains(status) {
+                        viewModel.statusFilter.remove(status)
+                    } else {
+                        viewModel.statusFilter.insert(status)
+                    }
+                } label: {
+                    // `Label(_:systemImage:)` with an empty string logs "No
+                    // symbol named ''" — use the icon-closure init instead so
+                    // the unselected case can render no icon at all.
+                    Label {
+                        Text(status.rawValue.capitalized)
+                    } icon: {
+                        if viewModel.statusFilter.contains(status) {
+                            Image(systemName: "checkmark")
+                        }
+                    }
+                }
+            }
+        } label: {
+            Text(viewModel.statusFilter.isEmpty ? "Any Status" : "\(viewModel.statusFilter.count) Status")
+        }
+        .padding(.horizontal, 4)
+    }
+
+    @ViewBuilder
+    private var results: some View {
+        if viewModel.isSearching && viewModel.results.isEmpty {
+            ProgressView()
+                .frame(maxWidth: .infinity, maxHeight: .infinity)
+        } else if let errorMessage = viewModel.errorMessage {
+            ContentUnavailableView {
+                Label("Search Failed", systemImage: "exclamationmark.triangle")
+            } description: {
+                Text(errorMessage)
+            }
+        } else if viewModel.results.isEmpty {
+            ContentUnavailableView.search(text: query)
+        } else {
+            List(viewModel.results) { result in
+                NavigationLink(value: result.document) {
+                    VStack(alignment: .leading, spacing: 4) {
+                        DocumentRowView(document: result.document)
+                        Text(result.context)
+                            .font(.callout)
+                            .foregroundStyle(.secondary)
+                            .lineLimit(2)
+                    }
+                    .padding(.vertical, 2)
+                }
+            }
+        }
+    }
+}
+#endif
diff --git a/Outpost/Features/Search/GlobalSearchViewModel.swift b/Outpost/Features/Search/GlobalSearchViewModel.swift
new file mode 100644
index 0000000..a97324e
--- /dev/null
+++ b/Outpost/Features/Search/GlobalSearchViewModel.swift
@@ -0,0 +1,62 @@
+import Foundation
+import Observation
+import OutlineKit
+
+/// Backs the sidebar's whole-workspace search — full-text via `documents.search`,
+/// with filters mirroring what that endpoint actually supports.
+@MainActor
+@Observable
+final class GlobalSearchViewModel {
+    var results: [OutlineDocumentSearchResult] = []
+    var availableCollections: [OutlineCollection] = []
+    var isSearching = false
+    var errorMessage: String?
+
+    var collectionFilter: OutlineCollection?
+    var dateFilter: DocumentSearchDateFilter?
+    var sort: DocumentSearchSort = .relevance
+    var direction: DocumentSearchDirection = .descending
+    var statusFilter: Set<DocumentStatusFilter> = []
+
+    private let apiClient: OutlineAPIClient
+
+    init(apiClient: OutlineAPIClient) {
+        self.apiClient = apiClient
+    }
+
+    func loadCollectionsIfNeeded() async {
+        guard availableCollections.isEmpty else { return }
+        availableCollections = (try? await apiClient.listCollections(offset: 0, limit: 100)) ?? []
+    }
+
+    func search(query: String) async {
+        let trimmed = query.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !trimmed.isEmpty else {
+            results = []
+            errorMessage = nil
+            return
+        }
+
+        isSearching = true
+        errorMessage = nil
+        defer { isSearching = false }
+
+        do {
+            results = try await apiClient.searchDocuments(
+                DocumentSearchRequest(
+                    query: trimmed,
+                    collectionId: collectionFilter?.id,
+                    statusFilter: statusFilter.isEmpty ? nil : Array(statusFilter),
+                    dateFilter: dateFilter,
+                    // The server rejects `sort: "relevance"` outright — it's
+                    // apparently only valid as the *implicit* default when the
+                    // field is omitted entirely, not as an explicit value.
+                    sort: sort == .relevance ? nil : sort,
+                    direction: direction
+                )
+            )
+        } catch {
+            errorMessage = outlineErrorMessage(error, fallback: "Search failed. Try again.")
+        }
+    }
+}
diff --git a/Outpost/Features/Search/SidebarSearchField.swift b/Outpost/Features/Search/SidebarSearchField.swift
new file mode 100644
index 0000000..213867f
--- /dev/null
+++ b/Outpost/Features/Search/SidebarSearchField.swift
@@ -0,0 +1,30 @@
+#if os(macOS)
+import SwiftUI
+
+struct SidebarSearchField: View {
+    @Binding var text: String
+
+    var body: some View {
+        HStack(spacing: 6) {
+            Image(systemName: "magnifyingglass")
+                .foregroundStyle(.secondary)
+            TextField("Search workspace…", text: $text)
+                .textFieldStyle(.plain)
+            if !text.isEmpty {
+                Button {
+                    text = ""
+                } label: {
+                    Image(systemName: "xmark.circle.fill")
+                        .foregroundStyle(.secondary)
+                }
+                .buttonStyle(.plain)
+            }
+        }
+        .padding(.horizontal, 10)
+        .padding(.vertical, 6)
+        .background(.fill.tertiary, in: RoundedRectangle(cornerRadius: 8))
+        .padding(.horizontal, 10)
+        .padding(.vertical, 8)
+    }
+}
+#endif
diff --git a/Outpost/Support/OutlineAPIError+Message.swift b/Outpost/Support/OutlineAPIError+Message.swift
new file mode 100644
index 0000000..012960f
--- /dev/null
+++ b/Outpost/Support/OutlineAPIError+Message.swift
@@ -0,0 +1,29 @@
+import Foundation
+import OutlineKit
+
+extension OutlineAPIError {
+    /// User-facing message, distinguishing failure causes instead of one blanket
+    /// "try again" — a 404 (e.g. an endpoint missing on an older server version)
+    /// looks nothing like a dropped connection, and surfacing that difference is
+    /// what actually helps diagnose it.
+    var userFacingMessage: String {
+        switch self {
+        case .unauthorized:
+            return "Sign-in expired. Try signing in again."
+        case .notFound:
+            return "That isn't available on this server."
+        case .transport:
+            return "Couldn't reach the server. Check your connection."
+        case .server(let status, let message):
+            return message ?? "The server returned an error (\(status))."
+        case .decoding:
+            return "Got an unexpected response from the server."
+        case .tokenUnavailable:
+            return "Couldn't access your saved sign-in."
+        }
+    }
+}
+
+func outlineErrorMessage(_ error: Error, fallback: String) -> String {
+    (error as? OutlineAPIError)?.userFacingMessage ?? fallback
+}