diff --git a/supacode/Clients/Updates/UpdaterClient.swift b/supacode/Clients/Updates/UpdaterClient.swift
index e0e9e532..5af4d499 100644
--- a/supacode/Clients/Updates/UpdaterClient.swift
+++ b/supacode/Clients/Updates/UpdaterClient.swift
@@ -1,3 +1,4 @@
+import AppKit
 import ComposableArchitecture
 import Sparkle
 
@@ -65,13 +66,17 @@ final class SilentUpdateDriver: NSObject, SPUUserDriver {
   ) {
     MainActor.assumeIsolated {
       if state.userInitiated {
+        if shouldConfirmInstallAndRelaunchImmediately(for: state.stage) {
+          reply(confirmInstallAndRelaunchChoice())
+          return
+        }
         standard.showUpdateFound(with: appcastItem, state: state, reply: reply)
         return
       }
       // Background check: surface the availability silently, then defer so Sparkle
       // will re-offer the same update on the next (user-initiated) check.
       continuation?.yield(.silentUpdateFound(version: appcastItem.displayVersionString))
-      reply(.dismiss)
+      reply(silentBackgroundUpdateChoice(for: state.stage))
     }
   }
 
@@ -137,7 +142,7 @@ final class SilentUpdateDriver: NSObject, SPUUserDriver {
 
   nonisolated func showReady(toInstallAndRelaunch reply: @escaping @Sendable (SPUUserUpdateChoice) -> Void) {
     MainActor.assumeIsolated {
-      standard.showReady(toInstallAndRelaunch: reply)
+      reply(confirmInstallAndRelaunchChoice())
     }
   }
 
@@ -175,6 +180,35 @@ final class SilentUpdateDriver: NSObject, SPUUserDriver {
   }
 }
 
+func silentBackgroundUpdateChoice(for stage: SPUUserUpdateStage) -> SPUUserUpdateChoice {
+  switch stage {
+  case .notDownloaded, .downloaded:
+    .dismiss
+  case .installing:
+    .skip
+  @unknown default:
+    .dismiss
+  }
+}
+
+func installAndRelaunchChoice(didConfirm: Bool) -> SPUUserUpdateChoice {
+  didConfirm ? .install : .skip
+}
+
+func shouldConfirmInstallAndRelaunchImmediately(for stage: SPUUserUpdateStage) -> Bool {
+  stage == .installing
+}
+
+@MainActor
+private func confirmInstallAndRelaunchChoice() -> SPUUserUpdateChoice {
+  let alert = NSAlert()
+  alert.messageText = "Install Update and Relaunch?"
+  alert.informativeText = "Prowl will quit and relaunch to finish installing the update."
+  alert.addButton(withTitle: "Install and Relaunch")
+  alert.addButton(withTitle: "Later")
+  return installAndRelaunchChoice(didConfirm: alert.runModal() == .alertFirstButtonReturn)
+}
+
 extension UpdaterClient: DependencyKey {
   static let liveValue: UpdaterClient = {
     let hostBundle = Bundle.main
diff --git a/supacodeTests/UpdaterClientTests.swift b/supacodeTests/UpdaterClientTests.swift
new file mode 100644
index 00000000..e9850b43
--- /dev/null
+++ b/supacodeTests/UpdaterClientTests.swift
@@ -0,0 +1,23 @@
+import Sparkle
+import Testing
+
+@testable import supacode
+
+struct UpdaterClientTests {
+  @Test func backgroundUpdateDoesNotPreserveInstallingState() {
+    #expect(silentBackgroundUpdateChoice(for: .notDownloaded) == .dismiss)
+    #expect(silentBackgroundUpdateChoice(for: .downloaded) == .dismiss)
+    #expect(silentBackgroundUpdateChoice(for: .installing) == .skip)
+  }
+
+  @Test func installAndRelaunchRequiresConfirmation() {
+    #expect(installAndRelaunchChoice(didConfirm: true) == .install)
+    #expect(installAndRelaunchChoice(didConfirm: false) == .skip)
+  }
+
+  @Test func userInitiatedInstallingUpdateRequiresImmediateConfirmation() {
+    #expect(!shouldConfirmInstallAndRelaunchImmediately(for: .notDownloaded))
+    #expect(!shouldConfirmInstallAndRelaunchImmediately(for: .downloaded))
+    #expect(shouldConfirmInstallAndRelaunchImmediately(for: .installing))
+  }
+}