diff --git a/macos/Sources/Features/Update/UpdatePill.swift b/macos/Sources/Features/Update/UpdatePill.swift
index dda9ad607..1dc29e250 100644
--- a/macos/Sources/Features/Update/UpdatePill.swift
+++ b/macos/Sources/Features/Update/UpdatePill.swift
@@ -15,13 +15,29 @@ struct UpdatePill: View {
                     UpdatePopoverView(model: model)
                 }
                 .transition(.opacity.combined(with: .scale(scale: 0.95)))
+                .onChange(of: model.state) { newState in
+                    if case .notFound = newState {
+                        Task {
+                            try? await Task.sleep(for: .seconds(5))
+                            if case .notFound = model.state {
+                                model.state = .idle
+                            }
+                        }
+                    }
+                }
         }
     }
     
     /// The pill-shaped button view that displays the update badge and text
     @ViewBuilder
     private var pillButton: some View {
-        Button(action: { showPopover.toggle() }) {
+        Button(action: {
+            if case .notFound = model.state {
+                model.state = .idle
+            } else {
+                showPopover.toggle()
+            }
+        }) {
             HStack(spacing: 6) {
                 UpdateBadge(model: model)
                     .frame(width: 14, height: 14)
diff --git a/macos/Sources/Features/Update/UpdateViewModel.swift b/macos/Sources/Features/Update/UpdateViewModel.swift
index 57e438bcd..05f7eef9a 100644
--- a/macos/Sources/Features/Update/UpdateViewModel.swift
+++ b/macos/Sources/Features/Update/UpdateViewModel.swift
@@ -87,6 +87,8 @@ class UpdateViewModel: ObservableObject {
             return .accentColor
         case .readyToInstall:
             return Color(nsColor: NSColor.systemGreen.blended(withFraction: 0.3, of: .black) ?? .systemGreen)
+        case .notFound:
+            return Color(nsColor: NSColor.systemBlue.blended(withFraction: 0.5, of: .black) ?? .systemBlue)
         case .error:
             return .orange.opacity(0.2)
         default:
@@ -99,6 +101,8 @@ class UpdateViewModel: ObservableObject {
         switch state {
         case .updateAvailable, .readyToInstall:
             return .white
+        case .notFound:
+            return .white
         case .error:
             return .orange
         default:
@@ -107,7 +111,7 @@ class UpdateViewModel: ObservableObject {
     }
 }
 
-enum UpdateState {
+enum UpdateState: Equatable {
     case idle
     case permissionRequest(PermissionRequest)
     case checking(Checking)
@@ -124,6 +128,33 @@ enum UpdateState {
         return false
     }
     
+    static func == (lhs: UpdateState, rhs: UpdateState) -> Bool {
+        switch (lhs, rhs) {
+        case (.idle, .idle):
+            return true
+        case (.permissionRequest, .permissionRequest):
+            return true
+        case (.checking, .checking):
+            return true
+        case (.updateAvailable(let lUpdate), .updateAvailable(let rUpdate)):
+            return lUpdate.appcastItem.displayVersionString == rUpdate.appcastItem.displayVersionString
+        case (.notFound, .notFound):
+            return true
+        case (.error(let lErr), .error(let rErr)):
+            return lErr.error.localizedDescription == rErr.error.localizedDescription
+        case (.downloading(let lDown), .downloading(let rDown)):
+            return lDown.progress == rDown.progress && lDown.expectedLength == rDown.expectedLength
+        case (.extracting(let lExt), .extracting(let rExt)):
+            return lExt.progress == rExt.progress
+        case (.readyToInstall, .readyToInstall):
+            return true
+        case (.installing, .installing):
+            return true
+        default:
+            return false
+        }
+    }
+    
     struct PermissionRequest {
         let request: SPUUpdatePermissionRequest
         let reply: @Sendable (SUUpdatePermissionResponse) -> Void