WIP: add pinboard-style search filters

README.md

@@ -16,7 +16,7 @@ The project is intentionally dependency-light: Swift Package Manager, AppKit, Ca
   - `Shift + Command + N` creates a new collection
 - Clipboard history for text, URLs with local preview thumbnails when available, images, audio, RTF/HTML rich text, PDFs, and file references
 - SQLite persistence with bounded history, pinned-item retention, and encrypted app-managed payloads
-- Search with independent token matching, structured filters such as `app:Safari`, `type:image`, `date:2026-06-30`, result jump-back to full history, and optional local OCR for copied images
+- Search with independent token matching, structured filters such as `app:Safari`, `type:image,pdf`, `pinboard:"Client Work","Read Later"`, `date:2026-06-30`, result jump-back to full history, and optional local OCR for copied images
 - Sort modes for recent, most used, images, links, text, files, audio, and pinned items
 - Custom named collections, including empty color-coded collections, for organizing clips from the card Collect control, context menu, or by dragging cards onto collection chips; collection chips can be edited or deleted from their context menu
 - Searchable custom titles for clips, so media, files, links, PDFs, audio, and text can be renamed without changing the copied payload

docs/SMOKE_TEST.md

@@ -33,20 +33,21 @@ Use this checklist before a release or after changes to panel, pasteboard, setti
 
 1. Open the panel and confirm the search field is focused.
 2. Type a query and confirm results filter immediately.
-3. Use arrow keys to move selection while the search field is focused.
-4. Right-click a filtered result and choose Show in Clipboard, or press `Command + G`, and confirm search clears while the same card stays selected in Most Recent.
-5. Press `Esc` once with a non-empty search field and confirm search clears.
-6. Press `Esc` again and confirm the panel closes.
-7. Reopen the panel, change sort segments, and confirm each segment updates results.
-8. Press `Shift + Command + N` or the collection rail `+`, enter `Client Work`, choose a color, and confirm a Client Work chip appears with 0 clips and an empty collection view.
-9. Return to Clipboard, select a card, use its Collect button to choose Client Work, and confirm the Client Work chip count increases.
-10. Select the Client Work chip and confirm the rail filters to assigned items, cards use the Client Work name/color in their headers, and the collection/color/assignment persists after quitting and reopening ClipBored.
-11. Right-click the Client Work chip, choose Edit Collection..., rename it, change its color, and confirm the chip and assigned card headers update.
-12. Right-click a media, file, link, PDF, audio, or text card, choose Rename..., give it a title, and confirm the card title and search results use the custom title while paste/copy still uses the original payload.
-13. Double-click an item and confirm it attempts to paste or falls back to copy without creating a duplicate history entry.
-14. Right-click a card, use Capture Rules to ignore its source app, copy from that app again, and confirm the new item is skipped.
-15. Drag an unassigned card onto the renamed collection chip and confirm the chip count increases and the card appears when that collection is selected.
-16. Resize or test on a narrow display and confirm the bottom shelf switches to compact cards that still show two recent clips cleanly.
+3. Type a structured query such as `pinboard:"Client Work","Read Later" type:image,pdf` and confirm only clips from those collections and content types remain.
+4. Use arrow keys to move selection while the search field is focused.
+5. Right-click a filtered result and choose Show in Clipboard, or press `Command + G`, and confirm search clears while the same card stays selected in Most Recent.
+6. Press `Esc` once with a non-empty search field and confirm search clears.
+7. Press `Esc` again and confirm the panel closes.
+8. Reopen the panel, change sort segments, and confirm each segment updates results.
+9. Press `Shift + Command + N` or the collection rail `+`, enter `Client Work`, choose a color, and confirm a Client Work chip appears with 0 clips and an empty collection view.
+10. Return to Clipboard, select a card, use its Collect button to choose Client Work, and confirm the Client Work chip count increases.
+11. Select the Client Work chip and confirm the rail filters to assigned items, cards use the Client Work name/color in their headers, and the collection/color/assignment persists after quitting and reopening ClipBored.
+12. Right-click the Client Work chip, choose Edit Collection..., rename it, change its color, and confirm the chip and assigned card headers update.
+13. Right-click a media, file, link, PDF, audio, or text card, choose Rename..., give it a title, and confirm the card title and search results use the custom title while paste/copy still uses the original payload.
+14. Double-click an item and confirm it attempts to paste or falls back to copy without creating a duplicate history entry.
+15. Right-click a card, use Capture Rules to ignore its source app, copy from that app again, and confirm the new item is skipped.
+16. Drag an unassigned card onto the renamed collection chip and confirm the chip count increases and the card appears when that collection is selected.
+17. Resize or test on a narrow display and confirm the bottom shelf switches to compact cards that still show two recent clips cleanly.
 
 ## Copy And Paste
 

sources/clipbored/views/ClipboardPanelViewModel.swift

@@ -13,8 +13,8 @@ final class ClipboardPanelViewModel {
 
   private struct ParsedSearchQuery {
     var textTokens: [String] = []
-    var appTokens: [String] = []
-    var collectionTokens: [String] = []
+    var appTokenGroups: [[String]] = []
+    var collectionTokenGroups: [[String]] = []
     var typeKinds: Set<ClipboardItemKind> = []
     var createdAfter: Date?
     var createdBefore: Date?
@@ -22,8 +22,8 @@ final class ClipboardPanelViewModel {
 
     var isEmpty: Bool {
       textTokens.isEmpty
-        && appTokens.isEmpty
-        && collectionTokens.isEmpty
+        && appTokenGroups.isEmpty
+        && collectionTokenGroups.isEmpty
         && typeKinds.isEmpty
         && createdAfter == nil
         && createdBefore == nil
@@ -793,19 +793,23 @@ final class ClipboardPanelViewModel {
       guard query.textTokens.allSatisfy({ text.contains($0) }) else { return false }
     }
 
-    if !query.appTokens.isEmpty {
+    if !query.appTokenGroups.isEmpty {
       let source = [item.sourceApp, item.sourceAppBundleId]
         .compactMap { $0?.lowercased() }
         .joined(separator: " ")
       guard !source.isEmpty,
-            query.appTokens.allSatisfy({ source.contains($0) }) else {
+            query.appTokenGroups.contains(where: { group in
+              group.allSatisfy { source.contains($0) }
+            }) else {
         return false
       }
     }
 
-    if !query.collectionTokens.isEmpty {
+    if !query.collectionTokenGroups.isEmpty {
       guard let collection = item.collectionName?.lowercased(),
-            query.collectionTokens.allSatisfy({ collection.contains($0) }) else {
+            query.collectionTokenGroups.contains(where: { group in
+              group.allSatisfy { collection.contains($0) }
+            }) else {
         return false
       }
     }
@@ -831,7 +835,7 @@ final class ClipboardPanelViewModel {
 
   private func parseSearchQuery(_ query: String) -> ParsedSearchQuery {
     var parsed = ParsedSearchQuery()
-    for part in query.split(whereSeparator: { $0.isWhitespace }).map(String.init) {
+    for part in searchParts(from: query) {
       guard !part.isEmpty else { continue }
       guard let delimiter = part.firstIndex(of: ":") else {
         parsed.textTokens.append(contentsOf: searchTokens(from: part.lowercased()))
@@ -852,14 +856,23 @@ final class ClipboardPanelViewModel {
   private func applyStructuredSearchToken(key: String, value: String, to query: inout ParsedSearchQuery) -> Bool {
     switch key {
     case "app", "source", "from":
-      query.appTokens.append(contentsOf: searchTokens(from: value))
+      let groups = structuredTokenGroups(from: value)
+      guard !groups.isEmpty else { return false }
+      query.appTokenGroups.append(contentsOf: groups)
       return true
-    case "collection", "folder", "list":
-      query.collectionTokens.append(contentsOf: searchTokens(from: value))
+    case "collection", "folder", "list", "pinboard", "pinboards", "board", "boards":
+      let groups = structuredTokenGroups(from: value)
+      guard !groups.isEmpty else { return false }
+      query.collectionTokenGroups.append(contentsOf: groups)
       return true
     case "type", "kind":
-      guard let kinds = itemKinds(matching: value), !kinds.isEmpty else { return false }
-      query.typeKinds.formUnion(kinds)
+      var matchedKinds = Set<ClipboardItemKind>()
+      for segment in structuredValueSegments(from: value) {
+        guard let kinds = itemKinds(matching: segment), !kinds.isEmpty else { return false }
+        matchedKinds.formUnion(kinds)
+      }
+      guard !matchedKinds.isEmpty else { return false }
+      query.typeKinds.formUnion(matchedKinds)
       return true
     case "pin", "pinned":
       guard let pinned = booleanValue(from: value) else { return false }
@@ -886,6 +899,55 @@ final class ClipboardPanelViewModel {
     }
   }
 
+  private func searchParts(from query: String) -> [String] {
+    var parts: [String] = []
+    var current = ""
+    var quotedBy: Character?
+
+    func flushCurrent() {
+      let part = current.clipboardTrimmed
+      if !part.isEmpty {
+        parts.append(part)
+      }
+      current = ""
+    }
+
+    for character in query {
+      if character == "\"" || character == "'" {
+        if quotedBy == character {
+          quotedBy = nil
+          continue
+        }
+        if quotedBy == nil {
+          quotedBy = character
+          continue
+        }
+      }
+
+      if character.isWhitespace && quotedBy == nil {
+        flushCurrent()
+      } else {
+        current.append(character)
+      }
+    }
+
+    flushCurrent()
+    return parts
+  }
+
+  private func structuredValueSegments(from value: String) -> [String] {
+    value
+      .split(separator: ",")
+      .map { String($0).clipboardTrimmed.lowercased() }
+      .filter { !$0.isEmpty }
+  }
+
+  private func structuredTokenGroups(from value: String) -> [[String]] {
+    structuredValueSegments(from: value)
+      .map { searchTokens(from: $0) }
+      .filter { !$0.isEmpty }
+  }
+
   private func itemKinds(matching value: String) -> Set<ClipboardItemKind>? {
     switch value {
     case "text", "plain":

tests/clipboredtests/ClipboardPanelViewModelTests.swift

@@ -145,6 +145,85 @@ final class ClipboardPanelViewModelTests: XCTestCase {
     )
   }
 
+  func testStructuredSearchSupportsQuotedPinboardAndMultiValueFilters() {
+    let settings = makeSettings()
+    let store = makeStore(settings: settings)
+    let viewModel = ClipboardPanelViewModel(store: store, settings: settings, cacheService: ClipboardCacheService())
+    let items = [
+      ClipboardItem(
+        id: UUID(),
+        kind: .url,
+        displayText: "Launch link",
+        payload: "https://example.com/launch",
+        payloadHash: hash("launch-link"),
+        createdAt: Date(timeIntervalSince1970: 100),
+        lastUsedAt: Date(timeIntervalSince1970: 100),
+        useCount: 0,
+        sourceApp: "Safari",
+        imagePath: nil,
+        thumbnailPath: nil,
+        collectionName: "Useful Links"
+      ),
+      ClipboardItem(
+        id: UUID(),
+        kind: .image,
+        displayText: "Moodboard",
+        payload: "/tmp/moodboard.png",
+        payloadHash: hash("moodboard"),
+        createdAt: Date(timeIntervalSince1970: 300),
+        lastUsedAt: Date(timeIntervalSince1970: 300),
+        useCount: 0,
+        sourceApp: "Photos",
+        imagePath: nil,
+        thumbnailPath: nil,
+        collectionName: "Read Later"
+      ),
+      ClipboardItem(
+        id: UUID(),
+        kind: .file,
+        displayText: "Launch brief",
+        payload: "/tmp/brief.pdf",
+        payloadHash: hash("launch-brief"),
+        createdAt: Date(timeIntervalSince1970: 200),
+        lastUsedAt: Date(timeIntervalSince1970: 200),
+        useCount: 0,
+        sourceApp: "Finder",
+        imagePath: nil,
+        thumbnailPath: nil,
+        collectionName: "Client Work"
+      ),
+      ClipboardItem(
+        id: UUID(),
+        kind: .text,
+        displayText: "Standalone note",
+        payload: "outside",
+        payloadHash: hash("outside"),
+        createdAt: Date(timeIntervalSince1970: 400),
+        lastUsedAt: Date(timeIntervalSince1970: 400),
+        useCount: 0,
+        sourceApp: "Notes",
+        imagePath: nil,
+        thumbnailPath: nil
+      )
+    ]
+
+    XCTAssertEqual(
+      viewModel.computeVisibleItems(from: items, query: "pinboard:\"Client Work\"", sortMode: .mostRecent).map(\.displayText),
+      ["Launch brief"]
+    )
+    XCTAssertEqual(
+      viewModel.computeVisibleItems(from: items, query: "pinboard:\"Useful Links\",\"Read Later\"", sortMode: .mostRecent).map(\.displayText),
+      ["Moodboard", "Launch link"]
+    )
+    XCTAssertEqual(
+      viewModel.computeVisibleItems(from: items, query: "board:\"Client Work\" type:file,pdf", sortMode: .mostRecent).map(\.displayText),
+      ["Launch brief"]
+    )
+    XCTAssertTrue(
+      viewModel.computeVisibleItems(from: items, query: "pinboard:\"Client Work\" type:image", sortMode: .mostRecent).isEmpty
+    )
+  }
+
   func testStructuredSearchFiltersByCreatedDate() {
     let settings = makeSettings()
     let store = makeStore(settings: settings)