Fix v0.4 reader workflow issues

CHANGELOG.md

@@ -17,6 +17,18 @@
 - Documented `https://www.akkolli.net/ihatepdfs` as the project website and `akshaykolli@hotmail.com` as the support contact.
 - Clarified that the project is vibe coded and maintained with AI agents, and that feature requests and agent-assisted PRs are welcome under the QA guidelines.
 
+## Version 0.4.0 (build 7) - 2026-06-30
+
+Build 7 keeps the public v0.4 app version and prepares another upload with targeted reader workflow fixes.
+
+### Fixed
+
+- Added an always-visible Reply button to comment and reply rows in the comments sidebar.
+- Made Escape leave active annotation modes, including highlighter mode and free-text placement.
+- Kept the macOS full-screen shortcut available after focus moves to window chrome.
+- Added annotation undo/redo for add and delete operations.
+- Added selected-annotation deletion and visible delete controls for plain highlights.
+
 ## Version 0.4.0 (build 6) - 2026-06-25
 
 Version 0.4 removes the experimental Fill & Sign, form-field navigation, and PDF signing implementation from the shipping app. The release is back to a small native reader and annotation tool while preserving the size target.

README.md

@@ -40,7 +40,7 @@ Supported Mac architectures: Apple Silicon and Intel.
 
 ## Latest Release
 
-Current version: `0.4.0` build `6`.
+Current version: `0.4.0` build `7`.
 
 Download the v0.4 macOS DMG from the GitHub release page:
 
@@ -52,7 +52,7 @@ The direct-download DMG is separate from the Mac App Store build. The App Store
 
 ## Features
 
-- Incredibly small app size: v0.4 ships as a 957 KB direct-download DMG, with a 253 KB Apple Silicon archive and a 287 KB Intel archive.
+- Incredibly small app size: v0.4 ships as a 998 KB direct-download DMG, with a 255 KB Apple Silicon archive and a 288 KB Intel archive.
 - Extremely fast native PDF reading: built on SwiftUI, AppKit, and PDFKit instead of a bundled browser, runtime, database, or PDF engine.
 - Power- and size-efficient by design: minimal assets, no bundled services, and no background sync workload.
 - Local-first privacy: opens user-selected PDFs from disk and does not require accounts, analytics, tracking, or cloud upload.

docs/QA.md

@@ -16,21 +16,17 @@ Use this section as the source of truth when checking whether a feature matches
 
 ## Latest v0.4 Automated QA Run
 
-Completed on 2026-06-29:
+Completed on 2026-06-30 for build 7:
 
-- `swift build`
 - `swift test`
+- `swift scripts/verify-pdf-annotations.swift`
+- `swift build -c release --product IHatePDFs`
+- `scripts/build-app.sh`
+- `BUILD_APP=0 scripts/make-dmg.sh`
+- `scripts/make-tiny-archives.sh`
+- `PKG_PATH=dist/nonexistent-appstore.pkg scripts/verify-release-artifacts.sh`
 
-Before release, also run:
-
-```sh
-swift scripts/verify-pdf-annotations.swift
-swift build -c release --product IHatePDFs
-scripts/build-app.sh
-scripts/make-dmg.sh
-scripts/make-tiny-archives.sh
-scripts/verify-release-artifacts.sh
-```
+Before App Store upload, also run `scripts/make-app-store-pkg.sh` with the required signing identities and provisioning profile, then verify the generated package with `scripts/verify-release-artifacts.sh`.
 
 ## Test Files
 

scripts/release-version.sh

@@ -1,5 +1,5 @@
 #!/usr/bin/env bash
 
 APP_VERSION="${APP_VERSION:-0.4.0}"
-BUILD_NUMBER="${BUILD_NUMBER:-6}"
+BUILD_NUMBER="${BUILD_NUMBER:-7}"
 RELEASE_VERSION="${RELEASE_VERSION:-${APP_VERSION%.0}}"

sources/app/AppState.swift

@@ -60,6 +60,13 @@ enum AnnotationPlacementTool: Equatable {
     }
 }
 
+private struct AnnotationUndoRecord {
+    let annotation: PDFAnnotation
+    let page: PDFPage
+    let index: Int?
+    let popups: [PDFAnnotation]
+}
+
 private enum AppDefaults {
     static let documentPageProgress = "IHatePDFs.documentPageProgress.v1"
     static let documentBookmarks = "IHatePDFs.documentBookmarks.v1"
@@ -330,10 +337,28 @@ final class AppState: NSObject, ObservableObject {
             && !isHighlighterModeActive
     }
 
+    var canCancelActiveMode: Bool {
+        placementTool != nil || isHighlighterModeActive
+    }
+
     var canClearSearchQuery: Bool {
         !searchText.isEmpty || !searchResults.isEmpty
     }
 
+    var canDeleteSelectedAnnotation: Bool {
+        activeEditor == nil
+            && selectedAnnotationID != nil
+            && annotations.contains { $0.id == selectedAnnotationID }
+    }
+
+    var canUndoAnnotationChange: Bool {
+        annotationUndoManager?.canUndo == true
+    }
+
+    var canRedoAnnotationChange: Bool {
+        annotationUndoManager?.canRedo == true
+    }
+
     var searchSummaryText: String? {
         let query = searchText.trimmingCharacters(in: .whitespacesAndNewlines)
         guard !query.isEmpty else { return nil }
@@ -378,6 +403,10 @@ final class AppState: NSObject, ObservableObject {
         return [ReviewState.allStatuses] + preferred + custom
     }
 
+    private var annotationUndoManager: UndoManager? {
+        pdfView?.undoManager ?? hostingWindow?.undoManager
+    }
+
     var currentPageBookmark: PDFDocumentBookmark? {
         PDFDocumentBookmarks.bookmark(on: currentPageIndex, in: bookmarks)
     }
@@ -1065,6 +1094,25 @@ final class AppState: NSObject, ObservableObject {
         statusMessage = placementTool.cancellationMessage
     }
 
+    @discardableResult
+    func cancelActiveMode() -> Bool {
+        var messages: [String] = []
+
+        if let placementTool {
+            self.placementTool = nil
+            messages.append(placementTool.cancellationMessage)
+        }
+
+        if isHighlighterModeActive {
+            isHighlighterModeActive = false
+            messages.append("Highlighter off.")
+        }
+
+        guard !messages.isEmpty else { return false }
+        statusMessage = messages.joined(separator: " ")
+        return true
+    }
+
     func placePendingAnnotation(on page: PDFPage, near point: CGPoint) {
         guard let placementTool else { return }
 
@@ -1082,7 +1130,8 @@ final class AppState: NSObject, ObservableObject {
         }
 
         self.placementTool = nil
-        add(insertion)
+        let record = add(insertion)
+        registerUndoToRemoveAnnotations([record], actionName: "Add Free Text")
         refreshAnnotations(on: [page])
         openEditor(
             title: "Free Text",
@@ -1157,7 +1206,8 @@ final class AppState: NSObject, ObservableObject {
             author: author.isEmpty ? AnnotationFactory.defaultAuthor : author,
             parentID: parent.id
         )
-        add(insertion)
+        let record = add(insertion)
+        registerUndoToRemoveAnnotations([record], actionName: "Add Reply")
         clearSidebarReplyDraft()
         refreshAnnotations(on: [parent.page])
 
@@ -1205,17 +1255,20 @@ final class AppState: NSObject, ObservableObject {
         }
         let targetIDs = Set(targets.map(\.id))
         let targetPages = targets.map(\.page)
+        let actionName = deleteActionName(for: item, targetCount: targets.count)
 
         guard confirmDiscardSidebarReplyDraftIfNeeded(
             deleting: targetIDs,
-            actionName: targets.count > 1 ? "deleting this comment thread" : "deleting this comment"
+            actionName: deletingActionPhrase(for: item, targetCount: targets.count)
         ) else {
             return
         }
 
+        let records = annotationUndoRecords(for: targets)
         for target in targets {
             removeAnnotation(target.annotation, from: target.page)
         }
+        registerUndoToRestoreAnnotations(records, actionName: actionName)
 
         if selectedAnnotationID.map(targetIDs.contains) == true {
             selectedAnnotationID = nil
@@ -1227,7 +1280,27 @@ final class AppState: NSObject, ObservableObject {
 
         activeEditor = nil
         refreshAnnotations(on: targetPages)
-        statusMessage = targets.count > 1 ? "Comment thread deleted." : "Comment deleted."
+        statusMessage = deleteStatusMessage(for: item, targetCount: targets.count)
+    }
+
+    func deleteSelectedAnnotation() {
+        guard activeEditor == nil else { return }
+        guard let selectedAnnotationID,
+              let item = annotations.first(where: { $0.id == selectedAnnotationID })
+        else {
+            statusMessage = "Select an annotation before deleting."
+            return
+        }
+
+        delete(item)
+    }
+
+    func undoAnnotationChange() {
+        annotationUndoManager?.undo()
+    }
+
+    func redoAnnotationChange() {
+        annotationUndoManager?.redo()
     }
 
     func toggleReviewed(_ item: AnnotationSnapshot) {
@@ -1295,14 +1368,24 @@ final class AppState: NSObject, ObservableObject {
             }
         let targetIDs = Set(targets.map(\.id))
         let targetPages = targets.map(\.page)
+        let representative = targets.first ?? contextSnapshots.first
+        let actionName = representative.map {
+            deleteActionName(for: $0, targetCount: targets.isEmpty ? context.annotations.count : targets.count)
+        } ?? "Delete Annotation"
 
         guard confirmDiscardSidebarReplyDraftIfNeeded(
             deleting: targetIDs,
-            actionName: targets.count > 1 ? "deleting this comment thread" : "deleting this annotation"
+            actionName: representative.map {
+                deletingActionPhrase(for: $0, targetCount: targets.isEmpty ? context.annotations.count : targets.count)
+            } ?? "deleting this annotation"
         ) else {
             return
         }
 
+        let records = targets.isEmpty
+            ? annotationUndoRecords(for: context.annotations, pages: context.pages)
+            : annotationUndoRecords(for: targets)
+
         if targets.isEmpty {
             for (index, annotation) in context.annotations.enumerated() {
                 guard index < context.pages.count else { continue }
@@ -1313,6 +1396,7 @@ final class AppState: NSObject, ObservableObject {
                 removeAnnotation(target.annotation, from: target.page)
             }
         }
+        registerUndoToRestoreAnnotations(records, actionName: actionName)
 
         activeEditor = nil
         if targetIDs.isEmpty || selectedAnnotationID.map(targetIDs.contains) == true {
@@ -1326,7 +1410,9 @@ final class AppState: NSObject, ObservableObject {
         if context.isNewAnnotation {
             hasUnsavedChanges = context.hadUnsavedChangesBeforeCreation
         }
-        statusMessage = targets.count > 1 ? "Comment thread deleted." : "Annotation deleted."
+        statusMessage = representative.map {
+            deleteStatusMessage(for: $0, targetCount: targets.isEmpty ? context.annotations.count : targets.count)
+        } ?? "Annotation deleted."
     }
 
     func select(_ item: AnnotationSnapshot) {
@@ -1626,9 +1712,11 @@ final class AppState: NSObject, ObservableObject {
         }
 
         let hadUnsavedChangesBeforeCreation = hasUnsavedChanges
+        var records: [AnnotationUndoRecord] = []
         for insertion in insertions {
-            add(insertion)
+            records.append(add(insertion))
         }
+        registerUndoToRemoveAnnotations(records, actionName: addActionName(for: style))
         pdfView?.clearSelection()
         updateTextSelectionState()
         refreshAnnotations(on: insertions.map(\.page))
@@ -1654,7 +1742,8 @@ final class AppState: NSObject, ObservableObject {
         }
     }
 
-    private func add(_ insertion: AnnotationInsertion) {
+    @discardableResult
+    private func add(_ insertion: AnnotationInsertion) -> AnnotationUndoRecord {
         insertion.page.addAnnotation(insertion.annotation)
         if AnnotationKeys.isReply(insertion.annotation) {
             AnnotationFactory.hideReplyMarker(insertion.annotation, on: insertion.page)
@@ -1662,6 +1751,169 @@ final class AppState: NSObject, ObservableObject {
         detachPopupMarkerFromViewer(for: insertion.annotation, on: insertion.page)
         hasUnsavedChanges = true
         pdfView?.annotationsChanged(on: insertion.page)
+        return annotationUndoRecord(for: insertion.annotation, on: insertion.page)
+    }
+
+    private func registerUndoToRemoveAnnotations(
+        _ records: [AnnotationUndoRecord],
+        actionName: String
+    ) {
+        guard !records.isEmpty, let undoManager = annotationUndoManager else { return }
+
+        undoManager.registerUndo(withTarget: self) { target in
+            target.removeAnnotationsForUndo(records, actionName: actionName)
+        }
+        undoManager.setActionName(actionName)
+    }
+
+    private func registerUndoToRestoreAnnotations(
+        _ records: [AnnotationUndoRecord],
+        actionName: String
+    ) {
+        guard !records.isEmpty, let undoManager = annotationUndoManager else { return }
+
+        undoManager.registerUndo(withTarget: self) { target in
+            target.restoreAnnotationsForUndo(records, actionName: actionName)
+        }
+        undoManager.setActionName(actionName)
+    }
+
+    private func removeAnnotationsForUndo(
+        _ records: [AnnotationUndoRecord],
+        actionName: String
+    ) {
+        registerUndoToRestoreAnnotations(records, actionName: actionName)
+        clearStateForRemovedAnnotations(records.map(\.annotation))
+        for record in records {
+            removeAnnotation(record.annotation, from: record.page)
+        }
+        activeEditor = nil
+        refreshAnnotations(on: records.map(\.page))
+        statusMessage = "Annotation change undone."
+    }
+
+    private func restoreAnnotationsForUndo(
+        _ records: [AnnotationUndoRecord],
+        actionName: String
+    ) {
+        registerUndoToRemoveAnnotations(records, actionName: actionName)
+        for record in sortedUndoRecordsForRestore(records) {
+            restoreAnnotation(record)
+        }
+        activeEditor = nil
+        refreshAnnotations(on: records.map(\.page))
+        statusMessage = "Annotation change restored."
+    }
+
+    private func annotationUndoRecords(for targets: [AnnotationSnapshot]) -> [AnnotationUndoRecord] {
+        uniqueUndoRecords(targets.map { annotationUndoRecord(for: $0.annotation, on: $0.page) })
+    }
+
+    private func annotationUndoRecords(
+        for annotations: [PDFAnnotation],
+        pages: [PDFPage]
+    ) -> [AnnotationUndoRecord] {
+        let records = annotations.enumerated().compactMap { index, annotation -> AnnotationUndoRecord? in
+            guard index < pages.count else { return nil }
+            return annotationUndoRecord(for: annotation, on: pages[index])
+        }
+        return uniqueUndoRecords(records)
+    }
+
+    private func annotationUndoRecord(
+        for annotation: PDFAnnotation,
+        on page: PDFPage
+    ) -> AnnotationUndoRecord {
+        AnnotationUndoRecord(
+            annotation: annotation,
+            page: page,
+            index: page.annotations.firstIndex { $0 === annotation },
+            popups: linkedPopups(for: annotation, on: page)
+        )
+    }
+
+    private func uniqueUndoRecords(_ records: [AnnotationUndoRecord]) -> [AnnotationUndoRecord] {
+        var seen = Set<ObjectIdentifier>()
+        var result: [AnnotationUndoRecord] = []
+        for record in records {
+            let id = ObjectIdentifier(record.annotation)
+            guard seen.insert(id).inserted else { continue }
+            result.append(record)
+        }
+        return result
+    }
+
+    private func sortedUndoRecordsForRestore(_ records: [AnnotationUndoRecord]) -> [AnnotationUndoRecord] {
+        records.sorted { left, right in
+            switch (left.index, right.index) {
+            case let (leftIndex?, rightIndex?):
+                return leftIndex < rightIndex
+            case (_?, nil):
+                return true
+            case (nil, _?):
+                return false
+            case (nil, nil):
+                return false
+            }
+        }
+    }
+
+    private func restoreAnnotation(_ record: AnnotationUndoRecord) {
+        if record.annotation.page !== record.page {
+            record.page.addAnnotation(record.annotation)
+        }
+
+        for popup in record.popups where popup.page == nil {
+            record.page.addAnnotation(popup)
+        }
+
+        moveAnnotation(record.annotation, on: record.page, to: record.index)
+        detachPopupMarkerFromViewer(for: record.annotation, on: record.page)
+        hasUnsavedChanges = true
+        pdfView?.annotationsChanged(on: record.page)
+    }
+
+    private func moveAnnotation(_ annotation: PDFAnnotation, on page: PDFPage, to index: Int?) {
+        guard let index,
+              index >= 0,
+              index < page.annotations.count - 1
+        else {
+            return
+        }
+
+        let tail = page.annotations.dropFirst(index).filter { $0 !== annotation }
+        for annotation in tail {
+            page.removeAnnotation(annotation)
+        }
+        for annotation in tail {
+            page.addAnnotation(annotation)
+        }
+    }
+
+    private func clearStateForRemovedAnnotations(_ removedAnnotations: [PDFAnnotation]) {
+        let removed = Set(removedAnnotations.map(ObjectIdentifier.init))
+        let removedIDs = Set(annotations.compactMap { snapshot in
+            removed.contains(ObjectIdentifier(snapshot.annotation)) ? snapshot.id : nil
+        })
+
+        if selectedAnnotationID.map(removedIDs.contains) == true {
+            selectedAnnotationID = nil
+        }
+        if hoveredAnnotationID.map(removedIDs.contains) == true {
+            hoveredAnnotationID = nil
+        }
+        clearSidebarReplyDraftIfNeeded(deleting: removedIDs)
+    }
+
+    private func addActionName(for style: MarkupAnnotationStyle) -> String {
+        switch style {
+        case .highlight:
+            return "Add Highlight"
+        case .comment:
+            return "Add Comment"
+        case .underline:
+            return "Add Underline Comment"
+        }
     }
 
     private func updateTextSelectionState() {
@@ -1768,16 +2020,47 @@ final class AppState: NSObject, ObservableObject {
         return true
     }
 
-    private func removeAnnotation(_ annotation: PDFAnnotation, from page: PDFPage) {
-        let linkedPopups = page.annotations.filter { candidate in
-            guard AnnotationKeys.annotation(candidate, hasSubtype: .popup) else { return false }
-            return candidate === annotation.popup || AnnotationFactory.parentAnnotation(for: candidate) === annotation
+    private func deleteActionName(for item: AnnotationSnapshot, targetCount: Int) -> String {
+        "Delete \(deleteNounTitle(for: item, targetCount: targetCount))"
+    }
+
+    private func deletingActionPhrase(for item: AnnotationSnapshot, targetCount: Int) -> String {
+        "deleting this \(deleteNounSentence(for: item, targetCount: targetCount))"
+    }
+
+    private func deleteStatusMessage(for item: AnnotationSnapshot, targetCount: Int) -> String {
+        "\(deleteNounTitle(for: item, targetCount: targetCount)) deleted."
+    }
+
+    private func deleteNounTitle(for item: AnnotationSnapshot, targetCount: Int) -> String {
+        if targetCount > 1 {
+            return "Comment Thread"
         }
 
-        for popup in linkedPopups {
-            page.removeAnnotation(popup)
+        switch item.kind {
+        case .comment:
+            return "Comment"
+        case .highlight:
+            return "Highlight"
+        case .underline:
+            return "Underline Comment"
+        case .note:
+            return "Note"
+        case .freeText:
+            return "Free Text"
+        case .reply:
+            return "Reply"
+        case .other:
+            return "Annotation"
         }
-        if let popup = annotation.popup, popup.page != nil {
+    }
+
+    private func deleteNounSentence(for item: AnnotationSnapshot, targetCount: Int) -> String {
+        deleteNounTitle(for: item, targetCount: targetCount).lowercased()
+    }
+
+    private func removeAnnotation(_ annotation: PDFAnnotation, from page: PDFPage) {
+        for popup in linkedPopups(for: annotation, on: page) {
             page.removeAnnotation(popup)
         }
 
@@ -1786,6 +2069,22 @@ final class AppState: NSObject, ObservableObject {
         pdfView?.annotationsChanged(on: page)
     }
 
+    private func linkedPopups(for annotation: PDFAnnotation, on page: PDFPage) -> [PDFAnnotation] {
+        var seen = Set<ObjectIdentifier>()
+        var popups = page.annotations.filter { candidate in
+            guard AnnotationKeys.annotation(candidate, hasSubtype: .popup) else { return false }
+            return candidate === annotation.popup || AnnotationFactory.parentAnnotation(for: candidate) === annotation
+        }
+
+        if let popup = annotation.popup {
+            popups.append(popup)
+        }
+
+        return popups.filter { popup in
+            seen.insert(ObjectIdentifier(popup)).inserted
+        }
+    }
+
     private func openEditor(
         title: String,
         annotations: [PDFAnnotation],

sources/app/IHatePDFsApp.swift

@@ -88,6 +88,19 @@ private final class AppStateRegistry {
         }
     }
 
+    func appStateForActiveWindow() -> AppState? {
+        prune()
+
+        let candidateWindows = [NSApp.keyWindow, NSApp.mainWindow].compactMap { $0 }
+        for window in candidateWindows {
+            if let appState = appStates.compactMap(\.value).first(where: { $0.hostingWindow === window }) {
+                return appState
+            }
+        }
+
+        return nil
+    }
+
     private func prune() {
         appStates.removeAll { $0.value == nil }
     }
@@ -241,7 +254,11 @@ private final class WindowCloseGuardView: NSView {
 }
 
 private struct AppCommands: Commands {
-    @FocusedObject private var appState: AppState?
+    @FocusedObject private var focusedAppState: AppState?
+
+    private var appState: AppState? {
+        focusedAppState ?? AppStateRegistry.shared.appStateForActiveWindow()
+    }
 
     private var hasDocument: Bool {
         appState?.document != nil
@@ -259,6 +276,10 @@ private struct AppCommands: Commands {
         appState?.canSaveDocument == true
     }
 
+    private var canDeleteSelectedAnnotation: Bool {
+        appState?.canDeleteSelectedAnnotation == true
+    }
+
     private var recentDocumentURLs: [URL] {
         appState?.recentDocumentURLs ?? []
     }
@@ -408,6 +429,26 @@ private struct AppCommands: Commands {
         }
 
         CommandMenu("Annotate") {
+            Button("Undo Annotation Change") {
+                appState?.undoAnnotationChange()
+            }
+            .disabled(appState?.canUndoAnnotationChange != true)
+
+            Button("Redo Annotation Change") {
+                appState?.redoAnnotationChange()
+            }
+            .disabled(appState?.canRedoAnnotationChange != true)
+
+            Divider()
+
+            Button("Cancel Annotation Mode") {
+                appState?.cancelActiveMode()
+            }
+            .keyboardShortcut(.cancelAction)
+            .disabled(appState?.canCancelActiveMode != true)
+
+            Divider()
+
             Button(isHighlighterModeActive ? "Turn Highlighter Off" : "Turn Highlighter On") {
                 appState?.toggleHighlighterMode()
             }
@@ -431,6 +472,13 @@ private struct AppCommands: Commands {
             }
             .keyboardShortcut("t", modifiers: [.command, .shift])
             .disabled(!hasDocument)
+
+            Divider()
+
+            Button("Delete Selected Annotation") {
+                appState?.deleteSelectedAnnotation()
+            }
+            .disabled(!canDeleteSelectedAnnotation)
         }
 
         CommandMenu("Bookmark") {

sources/app/PDFKitRepresentedView.swift

@@ -6,7 +6,7 @@ import SwiftUI
 final class AcademicPDFView: PDFView {
     var onAnnotationClick: ((PDFAnnotation, PDFPage) -> Void)?
     var onPlacementClick: ((PDFPage, CGPoint) -> Void)?
-    var onCancelPlacement: (() -> Void)?
+    var onCancelActiveMode: (() -> Void)?
     var onSelectionComment: (() -> Void)?
     var onHighlighterSelection: (() -> Void)?
     var onToggleHighlighterKey: (() -> Void)?
@@ -14,6 +14,7 @@ final class AcademicPDFView: PDFView {
     var onCommentSelectionKey: (() -> Void)?
     var onPreviousPageKey: (() -> Void)?
     var onNextPageKey: (() -> Void)?
+    var onDeleteSelectedAnnotationKey: (() -> Void)?
     var placementTool: AnnotationPlacementTool? {
         didSet {
             guard oldValue != placementTool else { return }
@@ -118,8 +119,14 @@ final class AcademicPDFView: PDFView {
     }
 
     override func keyDown(with event: NSEvent) {
-        if event.keyCode == 53, placementTool != nil {
-            onCancelPlacement?()
+        if event.keyCode == 53, placementTool != nil || isHighlighterModeActive {
+            onCancelActiveMode?()
+            return
+        }
+
+        if [51, 117].contains(event.keyCode),
+           event.modifierFlags.intersection([.command, .control, .option, .shift]).isEmpty {
+            onDeleteSelectedAnnotationKey?()
             return
         }
 
@@ -506,9 +513,9 @@ struct PDFKitRepresentedView: NSViewRepresentable {
                 appState.placePendingAnnotation(on: page, near: point)
             }
         }
-        view.onCancelPlacement = {
+        view.onCancelActiveMode = {
             Task { @MainActor in
-                appState.cancelPlacementTool()
+                appState.cancelActiveMode()
             }
         }
         view.onSelectionComment = {
@@ -546,6 +553,11 @@ struct PDFKitRepresentedView: NSViewRepresentable {
                 appState.goToNextPage()
             }
         }
+        view.onDeleteSelectedAnnotationKey = {
+            Task { @MainActor in
+                appState.deleteSelectedAnnotation()
+            }
+        }
         appState.attachPDFView(view)
         return view
     }

sources/app/SidebarViews.swift

@@ -314,6 +314,7 @@ private struct HighlightGroupView: View {
 private struct HighlightRow: View {
     @EnvironmentObject private var appState: AppState
     @Environment(\.colorScheme) private var colorScheme
+    @State private var isRowHovered = false
     let item: AnnotationSnapshot
     let showsColorSwatch: Bool
 
@@ -322,49 +323,80 @@ private struct HighlightRow: View {
     }
 
     var body: some View {
-        Button {
-            appState.selectHighlightedText(item)
-        } label: {
-            HStack(alignment: .top, spacing: 8) {
-                Image(systemName: item.id == appState.selectedAnnotationID ? "largecircle.fill.circle" : "circle")
-                    .font(.caption2.weight(.semibold))
-                    .foregroundStyle(item.id == appState.selectedAnnotationID ? Color.accentColor : InterfacePalette.quietText(for: colorScheme))
-                    .frame(width: 14, height: 18)
-
-                if showsColorSwatch {
-                    Capsule()
-                        .fill(swatchColor)
-                        .frame(width: 20, height: 6)
-                        .overlay {
-                            Capsule()
-                                .stroke(InterfacePalette.hairline(for: colorScheme), lineWidth: 0.6)
-                        }
-                        .padding(.top, 6)
-                }
-
-                VStack(alignment: .leading, spacing: 4) {
-                    Text("p. \(item.pageLabel)")
-                        .font(.caption2.weight(.medium))
-                        .foregroundStyle(InterfacePalette.secondaryText(for: colorScheme))
-
-                    Text(item.highlightExcerpt)
-                        .font(.caption)
-                        .foregroundStyle(InterfacePalette.primaryText(for: colorScheme))
-                        .lineLimit(3)
-                        .fixedSize(horizontal: false, vertical: true)
-                }
+        HStack(alignment: .top, spacing: 6) {
+            Button {
+                appState.selectHighlightedText(item)
+            } label: {
+                highlightSummary
             }
-            .padding(.horizontal, 10)
-            .padding(.vertical, 7)
-            .frame(maxWidth: .infinity, alignment: .leading)
-            .contentShape(Rectangle())
-            .background(item.id == appState.selectedAnnotationID ? InterfacePalette.selectedRowFill(for: colorScheme) : Color.clear)
+            .buttonStyle(.plain)
+            .help("Go to highlight on page \(item.pageLabel)")
+
+            Button(role: .destructive) {
+                appState.delete(item)
+            } label: {
+                Image(systemName: "trash")
+                    .font(.caption2.weight(.semibold))
+                    .frame(width: 20, height: 20)
+                    .contentShape(Rectangle())
+            }
+            .buttonStyle(.plain)
+            .foregroundStyle(InterfacePalette.secondaryText(for: colorScheme))
+            .help("Delete Highlight")
+            .accessibilityLabel("Delete Highlight")
+            .opacity(isRowHovered || item.id == appState.selectedAnnotationID ? 1 : 0.68)
         }
-        .buttonStyle(.plain)
-        .help("Go to highlight on page \(item.pageLabel)")
+        .padding(.horizontal, 10)
+        .padding(.vertical, 7)
+        .frame(maxWidth: .infinity, alignment: .leading)
+        .contentShape(Rectangle())
+        .background(item.id == appState.selectedAnnotationID ? InterfacePalette.selectedRowFill(for: colorScheme) : Color.clear)
         .onHover { isHovered in
+            isRowHovered = isHovered
             appState.setCommentHover(item, isHovered: isHovered)
         }
+        .contextMenu {
+            Button(role: .destructive) {
+                appState.delete(item)
+            } label: {
+                Label("Delete Highlight", systemImage: "trash")
+            }
+        }
+    }
+
+    private var highlightSummary: some View {
+        HStack(alignment: .top, spacing: 8) {
+            Image(systemName: item.id == appState.selectedAnnotationID ? "largecircle.fill.circle" : "circle")
+                .font(.caption2.weight(.semibold))
+                .foregroundStyle(item.id == appState.selectedAnnotationID ? Color.accentColor : InterfacePalette.quietText(for: colorScheme))
+                .frame(width: 14, height: 18)
+
+            if showsColorSwatch {
+                Capsule()
+                    .fill(swatchColor)
+                    .frame(width: 20, height: 6)
+                    .overlay {
+                        Capsule()
+                            .stroke(InterfacePalette.hairline(for: colorScheme), lineWidth: 0.6)
+                    }
+                    .padding(.top, 6)
+            }
+
+            VStack(alignment: .leading, spacing: 4) {
+                Text("p. \(item.pageLabel)")
+                    .font(.caption2.weight(.medium))
+                    .foregroundStyle(InterfacePalette.secondaryText(for: colorScheme))
+
+                Text(item.highlightExcerpt)
+                    .font(.caption)
+                    .foregroundStyle(InterfacePalette.primaryText(for: colorScheme))
+                    .lineLimit(3)
+                    .fixedSize(horizontal: false, vertical: true)
+            }
+            .frame(maxWidth: .infinity, alignment: .leading)
+        }
+        .frame(maxWidth: .infinity, alignment: .leading)
+        .contentShape(Rectangle())
     }
 }
 
@@ -1287,26 +1319,41 @@ private struct CommentReviewRowActions: View {
     let onDelete: () -> Void
 
     var body: some View {
-        Menu {
-            Button(role: .none, action: onEdit) {
-                Label("Edit", systemImage: "pencil")
-            }
-            Button(role: .none, action: onReply) {
+        HStack(spacing: 5) {
+            Button(action: onReply) {
                 Label("Reply", systemImage: "arrowshape.turn.up.left")
+                    .font(.caption2.weight(.medium))
+                    .padding(.horizontal, 6)
+                    .padding(.vertical, 2)
+                    .contentShape(Capsule())
             }
-            Button(role: .destructive, action: onDelete) {
-                Label("Delete", systemImage: "trash")
+            .buttonStyle(.plain)
+            .help("Reply")
+            .accessibilityLabel("Reply")
+
+            Menu {
+                Button(role: .none, action: onEdit) {
+                    Label("Edit", systemImage: "pencil")
+                }
+                Button(role: .none, action: onReply) {
+                    Label("Reply", systemImage: "arrowshape.turn.up.left")
+                }
+                Button(role: .destructive, action: onDelete) {
+                    Label("Delete", systemImage: "trash")
+                }
+            } label: {
+                Image(systemName: "ellipsis")
+                    .font(.system(size: 11, weight: .semibold))
+                    .frame(width: 18, height: 18)
+                    .contentShape(Rectangle())
             }
-        } label: {
-            Image(systemName: "ellipsis")
-                .font(.system(size: 11, weight: .semibold))
-                .frame(width: 18, height: 18)
-                .contentShape(Rectangle())
+            .menuStyle(.borderlessButton)
+            .buttonStyle(.plain)
+            .menuIndicator(.hidden)
+            .opacity(isVisible ? 1 : 0)
+            .animation(.easeInOut(duration: 0.12), value: isVisible)
+            .help("More Actions")
+            .accessibilityLabel("More Actions")
         }
-        .menuStyle(.borderlessButton)
-        .buttonStyle(.plain)
-        .menuIndicator(.hidden)
-        .opacity(isVisible ? 1 : 0)
-        .animation(.easeInOut(duration: 0.12), value: isVisible)
     }
 }

tests/app/AppStateWorkflowTests.swift

@@ -246,6 +246,69 @@ final class AppStateWorkflowTests: XCTestCase {
         XCTAssertEqual(appState.saveHelpText, "Save PDF")
     }
 
+    func testCancelActiveModeClearsHighlighterAndPlacement() {
+        let appState = AppState()
+        appState.isHighlighterModeActive = true
+        appState.placementTool = .freeText
+
+        XCTAssertTrue(appState.canCancelActiveMode)
+        XCTAssertTrue(appState.cancelActiveMode())
+
+        XCTAssertFalse(appState.isHighlighterModeActive)
+        XCTAssertNil(appState.placementTool)
+        XCTAssertEqual(appState.statusMessage, "Free text placement canceled. Highlighter off.")
+        XCTAssertFalse(appState.canCancelActiveMode)
+    }
+
+    func testCancelActiveModeReturnsFalseWhenNoModeIsActive() {
+        let appState = AppState()
+
+        XCTAssertFalse(appState.canCancelActiveMode)
+        XCTAssertFalse(appState.cancelActiveMode())
+        XCTAssertEqual(appState.statusMessage, "Open a PDF to begin.")
+    }
+
+    func testDeleteSelectedHighlightCanUndoAndRedo() throws {
+        let url = try makeTemporaryPDF()
+        defer { try? FileManager.default.removeItem(at: url) }
+
+        let window = NSWindow()
+        let appState = AppState()
+        appState.hostingWindow = window
+        appState.loadDocument(from: url)
+
+        let page = try XCTUnwrap(appState.document?.page(at: 0))
+        let highlight = PDFAnnotation(
+            bounds: CGRect(x: 72, y: 650, width: 180, height: 18),
+            forType: .highlight,
+            withProperties: nil
+        )
+        highlight.markupType = .highlight
+        page.addAnnotation(highlight)
+        appState.refreshAnnotations(on: [page])
+
+        let item = try XCTUnwrap(appState.annotations.first { $0.annotation === highlight })
+        appState.selectHighlightedText(item)
+        XCTAssertTrue(appState.canDeleteSelectedAnnotation)
+
+        appState.deleteSelectedAnnotation()
+
+        XCTAssertFalse(page.annotations.contains { $0 === highlight })
+        XCTAssertTrue(appState.annotations.isEmpty)
+        XCTAssertTrue(appState.canUndoAnnotationChange)
+
+        appState.undoAnnotationChange()
+
+        XCTAssertTrue(page.annotations.contains { $0 === highlight })
+        XCTAssertEqual(appState.annotations.count, 1)
+        XCTAssertTrue(appState.canRedoAnnotationChange)
+
+        appState.redoAnnotationChange()
+
+        XCTAssertFalse(page.annotations.contains { $0 === highlight })
+        XCTAssertTrue(appState.annotations.isEmpty)
+    }
+
     private func makeTemporaryPDF() throws -> URL {
         let url = FileManager.default.temporaryDirectory
             .appendingPathComponent(UUID().uuidString)