diff --git a/Loop/Core/Observers/KeybindTrigger.swift b/Loop/Core/Observers/KeybindTrigger.swift
index 52cb4634..1617291f 100644
--- a/Loop/Core/Observers/KeybindTrigger.swift
+++ b/Loop/Core/Observers/KeybindTrigger.swift
@@ -103,6 +103,7 @@ final class KeybindTrigger {
 
             // If this is a valid event, don't passthrough
             let result = performKeybind(
+                keyCode: keyCode,
                 type: event.type,
                 isARepeat: event.getIntegerValueField(.keyboardEventAutorepeat) == 1,
                 flags: filteredFlags,
@@ -148,7 +149,7 @@ final class KeybindTrigger {
     ///   - flags: modifier flags associated with this event.
     ///   - isLoopOpen: whether Loop is currently open.
     /// - Returns: whether this event was processed by Loop.
-    private func performKeybind(type: CGEventType, isARepeat: Bool, flags: CGEventFlags, isLoopOpen: Bool) -> PerformKeybindResult {
+    private func performKeybind(keyCode: CGKeyCode, type: CGEventType, isARepeat: Bool, flags: CGEventFlags, isLoopOpen: Bool) -> PerformKeybindResult {
         let flagKeys = sideDependentTriggerKey ? flags.keyCodes : flags.keyCodes.baseModifiers
         let allPressedKeys: Set<CGKeyCode> = pressedKeys.union(flagKeys)
         let actionKeys: Set<CGKeyCode> = Set(allPressedKeys.subtracting(triggerKey).map(\.baseModifier))
@@ -172,7 +173,12 @@ final class KeybindTrigger {
 
         if type != .keyUp { // keyDown for flagsChanged
             if containsTrigger {
-                if let action = windowActionCache.actionsByKeybind[actionKeys] {
+                // Try an match directly with the action keys first, then fallback to just the key code.
+                // This prevents failures when the user is tapping the keys in rapid succession.
+                let initalMatch = windowActionCache.actionsByKeybind[actionKeys]
+                let fallbackMatch = windowActionCache.actionsByKeybind[[keyCode]]
+
+                if let action = initalMatch ?? fallbackMatch {
                     if !isARepeat || action.canRepeat {
                         openLoop(startingAction: action, overrideExistingTriggerDelayTimerAction: true)
                     }
diff --git a/Loop/Window Management/Window Manipulation/WindowEngine.swift b/Loop/Window Management/Window Manipulation/WindowEngine.swift
index c495af0d..6c564de5 100644
--- a/Loop/Window Management/Window Manipulation/WindowEngine.swift	
+++ b/Loop/Window Management/Window Manipulation/WindowEngine.swift	
@@ -11,6 +11,7 @@ import SwiftUI
 
 /// Handles execution of `WindowAction`s on windows within the user's workspace
 enum WindowEngine {
+    static var currentTask: Task<(), any Error>?
     /// Resize a Window
     /// - Parameters:
     ///   - window: Window to be resized
@@ -23,13 +24,16 @@ enum WindowEngine {
         on screen: NSScreen,
         completion: @escaping () -> () = {}
     ) {
-        Task.detached(priority: .userInitiated) {
+        currentTask?.cancel()
+        currentTask = Task.detached(priority: .userInitiated) {
             await resize(
                 window,
                 to: action,
                 on: screen
             )
 
+            try Task.checkCancellation()
+
             completion()
         }
     }
@@ -222,10 +226,12 @@ enum WindowEngine {
             try await window.setFrameAnimated(targetFrame, bounds: bounds)
         } else {
             window.setFrame(targetFrame, sizeFirst: willChangeScreens)
+            try Task.checkCancellation()
         }
 
         if !animate, !window.frame.approximatelyEqual(to: targetFrame) {
             window.setFrame(targetFrame)
+            try Task.checkCancellation()
         }
 
         handleSizeConstrainedWindow(window: window, bounds: bounds)
diff --git a/Loop/Window Management/Window/Window.swift b/Loop/Window Management/Window/Window.swift
index e13ceffd..349ee287 100644
--- a/Loop/Window Management/Window/Window.swift	
+++ b/Loop/Window Management/Window/Window.swift	
@@ -402,6 +402,7 @@ final class Window {
 
         try await withCheckedThrowingContinuation { (continuation: CheckedContinuation<(), Error>) in
             Task {
+                try Task.checkCancellation()
                 let animation = WindowTransformAnimation(
                     rect,
                     window: self,