diff --git a/Sources/AppDelegate.swift b/Sources/AppDelegate.swift
index b712734b..c2951cde 100644
--- a/Sources/AppDelegate.swift
+++ b/Sources/AppDelegate.swift
@@ -799,18 +799,27 @@ final class AppDelegate: NSObject, NSApplicationDelegate, UNUserNotificationCent
 
     #if DEBUG
     @objc func showUpdatePill(_ sender: Any?) {
+        updateViewModel.debugOverrideText = nil
+        updateViewModel.overrideState = .installing(.init(isAutoUpdate: true, retryTerminatingApplication: {}, dismiss: {}))
+    }
+
+    @objc func showUpdatePillLongNightly(_ sender: Any?) {
+        updateViewModel.debugOverrideText = "Update Available: 1.32.0-nightly+20260216.abc1234"
         updateViewModel.overrideState = .notFound(.init(acknowledgement: {}))
     }
 
     @objc func showUpdatePillLoading(_ sender: Any?) {
+        updateViewModel.debugOverrideText = nil
         updateViewModel.overrideState = .checking(.init(cancel: {}))
     }
 
     @objc func hideUpdatePill(_ sender: Any?) {
+        updateViewModel.debugOverrideText = nil
         updateViewModel.overrideState = .idle
     }
 
     @objc func clearUpdatePillOverride(_ sender: Any?) {
+        updateViewModel.debugOverrideText = nil
         updateViewModel.overrideState = nil
     }
 #endif
diff --git a/Sources/ContentView.swift b/Sources/ContentView.swift
index 18b7b15d..58444ba0 100644
--- a/Sources/ContentView.swift
+++ b/Sources/ContentView.swift
@@ -526,8 +526,8 @@ struct VerticalTabsSidebar: View {
     private let tabRowSpacing: CGFloat = 2
 
     var body: some View {
-        GeometryReader { proxy in
-            VStack(spacing: 0) {
+        VStack(spacing: 0) {
+            GeometryReader { proxy in
                 ScrollView {
                     VStack(spacing: 0) {
                         // Space for traffic lights
@@ -577,18 +577,18 @@ struct VerticalTabsSidebar: View {
                 }
                 .background(Color.clear)
                 .modifier(ClearScrollBackground())
-#if DEBUG
-                SidebarDevFooter(updateViewModel: updateViewModel)
-                    .frame(maxWidth: .infinity, alignment: .leading)
-#else
-                UpdatePill(model: updateViewModel)
-                    .padding(.leading, 10)
-                    .padding(.bottom, 10)
-                    .frame(maxWidth: .infinity, alignment: .leading)
-#endif
             }
-            .accessibilityIdentifier("Sidebar")
+#if DEBUG
+            SidebarDevFooter(updateViewModel: updateViewModel)
+                .frame(maxWidth: .infinity, alignment: .leading)
+#else
+            UpdatePill(model: updateViewModel)
+                .padding(.horizontal, 10)
+                .padding(.bottom, 10)
+                .frame(maxWidth: .infinity, alignment: .leading)
+#endif
         }
+        .accessibilityIdentifier("Sidebar")
         .ignoresSafeArea()
         .background(SidebarBackdrop().ignoresSafeArea())
         .onAppear {
@@ -740,7 +740,7 @@ private struct SidebarDevFooter: View {
                 .font(.system(size: 11, weight: .semibold))
                 .foregroundColor(.red)
         }
-        .padding(.leading, 10)
+        .padding(.horizontal, 10)
         .padding(.bottom, 10)
     }
 }
diff --git a/Sources/Update/UpdatePill.swift b/Sources/Update/UpdatePill.swift
index 0ff1f606..a976fee5 100644
--- a/Sources/Update/UpdatePill.swift
+++ b/Sources/Update/UpdatePill.swift
@@ -42,7 +42,7 @@ struct UpdatePill: View {
                     .font(Font(textFont))
                     .lineLimit(1)
                     .truncationMode(.tail)
-                    .frame(width: textWidth)
+                    .frame(maxWidth: textWidth, alignment: .leading)
             }
             .padding(.horizontal, 8)
             .padding(.vertical, 4)
diff --git a/Sources/Update/UpdateViewModel.swift b/Sources/Update/UpdateViewModel.swift
index 4644e745..8aa275af 100644
--- a/Sources/Update/UpdateViewModel.swift
+++ b/Sources/Update/UpdateViewModel.swift
@@ -6,12 +6,18 @@ import Sparkle
 class UpdateViewModel: ObservableObject {
     @Published var state: UpdateState = .idle
     @Published var overrideState: UpdateState?
+    #if DEBUG
+    @Published var debugOverrideText: String?
+    #endif
 
     var effectiveState: UpdateState {
         overrideState ?? state
     }
 
     var text: String {
+        #if DEBUG
+        if let debugOverrideText { return debugOverrideText }
+        #endif
         switch effectiveState {
         case .idle:
             return ""
diff --git a/Sources/cmuxApp.swift b/Sources/cmuxApp.swift
index 8c775dce..0eba58c4 100644
--- a/Sources/cmuxApp.swift
+++ b/Sources/cmuxApp.swift
@@ -202,6 +202,9 @@ struct cmuxApp: App {
                 Button("Show Update Pill") {
                     appDelegate.showUpdatePill(nil)
                 }
+                Button("Show Long Nightly Pill") {
+                    appDelegate.showUpdatePillLongNightly(nil)
+                }
                 Button("Show Loading State") {
                     appDelegate.showUpdatePillLoading(nil)
                 }