diff --git a/Snapzy/Features/Recording/RecordingCoordinator.swift b/Snapzy/Features/Recording/RecordingCoordinator.swift
index 9270d622c..a3ece5dc4 100644
--- a/Snapzy/Features/Recording/RecordingCoordinator.swift
+++ b/Snapzy/Features/Recording/RecordingCoordinator.swift
@@ -248,6 +248,12 @@ final class RecordingCoordinator: ObservableObject {
       "isActive": "\(isActive)",
       "recorderState": "\(recorder.state)",
     ])
+
+    guard recorder.state != .idle else {
+      cleanup()
+      return
+    }
+
     Task {
       await recorder.cancelRecording()
       cleanup()
@@ -281,6 +287,7 @@ final class RecordingCoordinator: ObservableObject {
     toolbarWindow = toolbar
 
     showRegionOverlay(for: rect, interactionEnabled: captureMode != .application)
+    toolbar.bringToFrontForInteraction()
     setupEscapeMonitors()
   }
 
diff --git a/Snapzy/Features/Recording/RecordingToolbarWindow.swift b/Snapzy/Features/Recording/RecordingToolbarWindow.swift
index 242ceb29f..3dbf3b975 100644
--- a/Snapzy/Features/Recording/RecordingToolbarWindow.swift
+++ b/Snapzy/Features/Recording/RecordingToolbarWindow.swift
@@ -6,9 +6,36 @@
 //
 
 import AppKit
+import Carbon.HIToolbox
 import Combine
 import SwiftUI
 
+@MainActor
+private final class RecordingToolbarHostingView<Content: View>: NSHostingView<Content> {
+  var onEscape: (() -> Void)?
+
+  override var acceptsFirstResponder: Bool {
+    true
+  }
+
+  override func acceptsFirstMouse(for event: NSEvent?) -> Bool {
+    true
+  }
+
+  override func keyDown(with event: NSEvent) {
+    guard event.keyCode == UInt16(kVK_Escape) else {
+      super.keyDown(with: event)
+      return
+    }
+
+    onEscape?()
+  }
+
+  override func cancelOperation(_ sender: Any?) {
+    onEscape?()
+  }
+}
+
 enum RecordingToolbarMode {
   case preRecord
   case recording
@@ -150,11 +177,11 @@ final class RecordingToolbarState: ObservableObject {
 // MARK: - Toolbar Window
 
 @MainActor
-final class RecordingToolbarWindow: NSWindow {
+final class RecordingToolbarWindow: NSPanel {
 
   private var anchorRect: CGRect
   private var mode: RecordingToolbarMode = .preRecord
-  private var hostingView: NSHostingView<AnyView>?
+  private var hostingView: RecordingToolbarHostingView<AnyView>?
   private var effectView: NSVisualEffectView?
   private var cachedContentSize: CGSize?
 
@@ -234,7 +261,9 @@ final class RecordingToolbarWindow: NSWindow {
     level = .popUpMenu
     collectionBehavior = [.canJoinAllSpaces, .fullScreenAuxiliary]
     hasShadow = true
+    isFloatingPanel = true
     isReleasedWhenClosed = false
+    hidesOnDeactivate = false
 
     // Apply theme appearance at window level (mirrors AnnotateWindow.applyTheme)
     appearance = ThemeManager.shared.nsAppearance
@@ -281,7 +310,11 @@ final class RecordingToolbarWindow: NSWindow {
 
   private func setContent(_ view: AnyView) {
     let themedView = view.preferredColorScheme(ThemeManager.shared.systemAppearance)
-    let hosting = NSHostingView(rootView: AnyView(themedView))
+    let hosting = RecordingToolbarHostingView(rootView: AnyView(themedView))
+    hosting.onEscape = { [weak self] in
+      guard self?.mode == .preRecord else { return }
+      self?.onCancel?()
+    }
     hosting.translatesAutoresizingMaskIntoConstraints = false
 
     // NSVisualEffectView provides native wallpaper-tinted material backing,
@@ -339,10 +372,38 @@ final class RecordingToolbarWindow: NSWindow {
   /// Position and order the window to the front (initial show only).
   private func showBelowRect(_ rect: CGRect) {
     positionBelowRect(rect)
+    bringToFrontForInteraction()
+  }
+
+  func bringToFrontForInteraction() {
+    NSApp.activate(ignoringOtherApps: true)
     orderFrontRegardless()
+    makeKey()
+    if let hostingView {
+      makeFirstResponder(hostingView)
+    }
   }
 
   override var canBecomeKey: Bool { true }
+  override var canBecomeMain: Bool { false }
+
+  override func keyDown(with event: NSEvent) {
+    guard mode == .preRecord, event.keyCode == UInt16(kVK_Escape) else {
+      super.keyDown(with: event)
+      return
+    }
+
+    onCancel?()
+  }
+
+  override func cancelOperation(_ sender: Any?) {
+    guard mode == .preRecord else {
+      super.cancelOperation(sender)
+      return
+    }
+
+    onCancel?()
+  }
 
   func updateAnchorRect(_ rect: CGRect) {
     anchorRect = rect
diff --git a/SnapzyTests/Services/Shortcuts/RecordingToolbarShortcutsTests.swift b/SnapzyTests/Services/Shortcuts/RecordingToolbarShortcutsTests.swift
index b48f7f0b6..b75f92abf 100644
--- a/SnapzyTests/Services/Shortcuts/RecordingToolbarShortcutsTests.swift
+++ b/SnapzyTests/Services/Shortcuts/RecordingToolbarShortcutsTests.swift
@@ -15,6 +15,45 @@ import XCTest
 
 final class RecordingToolbarShortcutsTests: XCTestCase {
 
+  @MainActor
+  func testPreRecordToolbarWindow_usesActivatingPanelForButtonClicks() {
+    let window = RecordingToolbarWindow(anchorRect: CGRect(x: 0, y: 0, width: 640, height: 360))
+    defer { window.close() }
+
+    XCTAssertTrue(window.styleMask.contains(.borderless))
+    XCTAssertFalse(window.styleMask.contains(.nonactivatingPanel))
+    XCTAssertTrue(window.canBecomeKey)
+    XCTAssertFalse(window.canBecomeMain)
+  }
+
+  @MainActor
+  func testPreRecordToolbarWindow_escapeInvokesCancel() throws {
+    let window = RecordingToolbarWindow(anchorRect: CGRect(x: 0, y: 0, width: 640, height: 360))
+    defer { window.close() }
+
+    var didCancel = false
+    window.onCancel = {
+      didCancel = true
+    }
+
+    let event = try XCTUnwrap(NSEvent.keyEvent(
+      with: .keyDown,
+      location: .zero,
+      modifierFlags: [],
+      timestamp: 0,
+      windowNumber: window.windowNumber,
+      context: nil,
+      characters: "\u{1b}",
+      charactersIgnoringModifiers: "\u{1b}",
+      isARepeat: false,
+      keyCode: UInt16(kVK_Escape)
+    ))
+
+    window.keyDown(with: event)
+
+    XCTAssertTrue(didCancel)
+  }
+
   // MARK: - GlobalShortcutKind & ShortcutAction Case Matching
 
   func testRecordingToolbarShortcuts_kindsArePresent() {