diff --git a/Loop/AppDelegate.swift b/Loop/AppDelegate.swift
index 78ed0204..eb36304e 100644
--- a/Loop/AppDelegate.swift
+++ b/Loop/AppDelegate.swift
@@ -27,16 +27,6 @@ class AppDelegate: NSObject, NSApplicationDelegate {
             await Defaults.iCloud.waitForSyncCompletion()
         }
 
-        // Check & ask for accessibility access
-        AccessibilityManager.requestAccess()
-        UNUserNotificationCenter.current().delegate = self
-
-        AppDelegate.requestNotificationAuthorization()
-
-        IconManager.refreshCurrentAppIcon()
-        AppDelegate.loopManager.start()
-        AppDelegate.windowDragManager.addObservers()
-
         if !launchedAsLoginItem {
             LuminareManager.open()
         } else {
@@ -45,6 +35,17 @@ class AppDelegate: NSObject, NSApplicationDelegate {
                 NSApp.setActivationPolicy(.accessory)
             }
         }
+
+        IconManager.refreshCurrentAppIcon()
+        AppDelegate.loopManager.start()
+        AppDelegate.windowDragManager.addObservers()
+
+        UNUserNotificationCenter.current().delegate = self
+        AppDelegate.requestNotificationAuthorization()
+
+        DispatchQueue.main.asyncAfter(deadline: .now() + 0.5) {
+            AccessibilityManager.requestAccess()
+        }
     }
 
     func applicationShouldTerminateAfterLastWindowClosed(_: NSApplication) -> Bool {
diff --git a/Loop/Luminare/Settings/Keybindings/CustomActionConfigurationView.swift b/Loop/Luminare/Settings/Keybindings/CustomActionConfigurationView.swift
index 66fa5846..32d5fa8c 100644
--- a/Loop/Luminare/Settings/Keybindings/CustomActionConfigurationView.swift
+++ b/Loop/Luminare/Settings/Keybindings/CustomActionConfigurationView.swift
@@ -43,19 +43,19 @@ struct CustomActionConfigurationView: View {
     }
 
     var body: some View {
-        ScreenView {
+        ScreenView(blurred: .constant(action.sizeMode != .custom)) {
             GeometryReader { geo in
-                let frame = action.getFrame(window: nil, bounds: CGRect(origin: .zero, size: geo.size), disablePadding: true)
-                let _ = print(frame)
                 ZStack {
                     if action.sizeMode == .custom {
+                        let frame = action.getFrame(window: nil, bounds: CGRect(origin: .zero, size: geo.size), disablePadding: true)
+
                         blurredWindow()
                             .frame(width: frame.width, height: frame.height)
                             .offset(x: frame.origin.x, y: frame.origin.y)
+                            .animation(LuminareSettingsWindow.animation, value: frame)
                     }
                 }
                 .frame(width: geo.size.width, height: geo.size.height, alignment: .topLeading)
-                .animation(LuminareSettingsWindow.animation, value: frame)
             }
         }
         .onChange(of: action) { windowAction = $0 }
@@ -303,9 +303,9 @@ struct CustomActionConfigurationView: View {
     @ViewBuilder private func blurredWindow() -> some View {
         VisualEffectView(material: .hudWindow, blendingMode: .withinWindow)
             .overlay {
-                RoundedRectangle(cornerRadius: 5)
-                    .strokeBorder(.white.opacity(0.1), lineWidth: 2)
+                RoundedRectangle(cornerRadius: 12 - 5)
+                    .strokeBorder(Color.getLoopAccent(tone: .normal), lineWidth: 2)
             }
-            .clipShape(RoundedRectangle(cornerRadius: 5))
+            .clipShape(RoundedRectangle(cornerRadius: 12 - 5))
     }
 }
diff --git a/Loop/Luminare/Settings/Keybindings/KeybindingItem.swift b/Loop/Luminare/Settings/Keybindings/KeybindingItem.swift
index cb3bb19b..ed46a8e8 100644
--- a/Loop/Luminare/Settings/Keybindings/KeybindingItem.swift
+++ b/Loop/Luminare/Settings/Keybindings/KeybindingItem.swift
@@ -94,11 +94,6 @@ struct KeybindingItemView: View {
                         }
                         .help("Customize what this keybind cycles through.")
                     }
-
-                    if isHovering {
-                        directionPicker()
-                            .help("Customize this keybind's action.")
-                    }
                 }
                 .font(.title3)
                 .foregroundStyle(isHovering ? .primary : .secondary)
@@ -137,6 +132,7 @@ struct KeybindingItemView: View {
                 .fixedSize()
             }
         }
+        .animation(LuminareSettingsWindow.animation, value: keybind)
         .padding(.horizontal, 12)
         .onAppear {
             computeSearchResults()
@@ -163,21 +159,26 @@ struct KeybindingItemView: View {
     }
 
     func label() -> some View {
-        HStack(spacing: 0) {
-            HStack(spacing: 8) {
-                IconView(action: $keybind)
-
-                Text(keybind.getName())
-                    .lineLimit(1)
-                    .contentTransition(.numericText())
-                    .animation(LuminareSettingsWindow.animation, value: keybind)
-            }
+        Button {
+            isPresented.toggle()
+        } label: {
+            HStack(spacing: 0) {
+                HStack(spacing: 8) {
+                    IconView(action: $keybind)
+
+                    Text(keybind.getName())
+                        .lineLimit(1)
+                        .contentTransition(.numericText())
+                }
 
-            if let info = keybind.direction.infoView {
-                info
+                if let info = keybind.direction.infoView {
+                    info
+                }
             }
+            .fixedSize(horizontal: false, vertical: true)
         }
-        .fixedSize(horizontal: false, vertical: true)
+        .buttonStyle(CompactButtonStyle())
+        .help("Customize this keybind's action.")
     }
 
     func directionPicker() -> some View {
@@ -225,3 +226,42 @@ struct KeybindingItemView: View {
         }
     }
 }
+
+private struct CompactButtonStyle: ButtonStyle {
+    @Environment(\.hoveringOverLuminareItem) var hoveringOverLuminareItem
+    @Environment(\.isEnabled) private var isEnabled: Bool
+    let elementMinHeight: CGFloat = 25
+    @State var isHovering: Bool = false
+    let cornerRadius: CGFloat = 6
+
+    public func makeBody(configuration: Configuration) -> some View {
+        configuration.label
+            .background {
+                if configuration.isPressed || isHovering || hoveringOverLuminareItem {
+                    backgroundForState(isPressed: configuration.isPressed)
+                        .background {
+                            RoundedRectangle(cornerRadius: cornerRadius)
+                                .strokeBorder(.quaternary, lineWidth: 1)
+                        }
+                        .clipShape(.rect(cornerRadius: cornerRadius))
+                        .padding(-4)
+                }
+            }
+            .onHover { isHovering = $0 }
+            .animation(LuminareSettingsWindow.fastAnimation, value: [isHovering, hoveringOverLuminareItem])
+            .frame(minHeight: elementMinHeight)
+            .opacity(isEnabled ? 1 : 0.5)
+    }
+
+    private func backgroundForState(isPressed: Bool) -> some View {
+        Group {
+            if isPressed {
+                Rectangle().foregroundStyle(.quaternary)
+            } else if isHovering {
+                Rectangle().foregroundStyle(.quaternary.opacity(0.6))
+            } else {
+                Rectangle().foregroundStyle(.quinary.opacity(0.5))
+            }
+        }
+    }
+}
diff --git a/Loop/Window Management/WindowAction+Image.swift b/Loop/Window Management/WindowAction+Image.swift
index 3543a536..8e428b8d 100644
--- a/Loop/Window Management/WindowAction+Image.swift	
+++ b/Loop/Window Management/WindowAction+Image.swift	
@@ -70,16 +70,6 @@ struct IconView: View {
                         .font(.system(size: 8))
                         .fontWeight(.bold)
                         .frame(width: size.width, height: size.height)
-                } else if action.direction == .cycle, action.cycle?.first == nil {
-                    Image(._18PxRepeat4)
-                        .resizable()
-                        .aspectRatio(contentMode: .fit)
-                        .frame(width: size.width, height: size.height)
-                } else if action.direction == .custom, frame == .zero {
-                    Image(._18PxSliders)
-                        .resizable()
-                        .aspectRatio(contentMode: .fit)
-                        .frame(width: size.width, height: size.height)
                 } else {
                     ZStack {
                         RoundedRectangle(cornerRadius: outerCornerRadius - inset)
diff --git a/Loop/Window Management/WindowEngine.swift b/Loop/Window Management/WindowEngine.swift
index 817bde91..3d6246bf 100644
--- a/Loop/Window Management/WindowEngine.swift	
+++ b/Loop/Window Management/WindowEngine.swift	
@@ -63,8 +63,8 @@ enum WindowEngine {
         let animate = Defaults[.animateWindowResizes] && !enhancedUI
         WindowRecords.record(window, action)
 
-        if window.nsRunningApplication == NSRunningApplication.current,
-           let window = NSApp.keyWindow {
+        if window.nsRunningApplication?.bundleIdentifier == Bundle.main.bundleIdentifier,
+           let window = NSApp.keyWindow ?? NSApp.windows.first {
             var newFrame = targetFrame
             newFrame.size = window.frame.size