diff --git a/BrewBar/BrewBarApp.swift b/BrewBar/BrewBarApp.swift
index 9df1548..793e41f 100644
--- a/BrewBar/BrewBarApp.swift
+++ b/BrewBar/BrewBarApp.swift
@@ -237,6 +237,8 @@ class AppDelegate: NSObject, NSApplicationDelegate {
     }
 
     @objc func upgradeAll() {
+        guard confirmUpgrade() else { return }
+
         statusMenuItem.title = "Upgrading..."
 
         runBrew("update") { _ in
@@ -246,6 +248,30 @@ class AppDelegate: NSObject, NSApplicationDelegate {
         }
     }
 
+    func confirmUpgrade() -> Bool {
+        let alert = NSAlert()
+        alert.alertStyle = .warning
+
+        if cachedOutdated.isEmpty {
+            alert.messageText = "Upgrade all outdated packages?"
+        } else {
+            alert.messageText = "Upgrade \(cachedOutdated.count) package\(cachedOutdated.count == 1 ? "" : "s")?"
+        }
+
+        var info = "Apps upgraded as casks (like a web browser) may be closed and replaced while running, without further warning. Save your work first."
+        if !cachedOutdated.isEmpty {
+            info += "\n\n" + cachedOutdated.joined(separator: "\n")
+        }
+        alert.informativeText = info
+
+        alert.addButton(withTitle: "Upgrade")
+        alert.addButton(withTitle: "Cancel")
+
+        // accessory app: bring the alert to the front, otherwise it can appear behind other windows
+        NSApp.activate(ignoringOtherApps: true)
+        return alert.runModal() == .alertFirstButtonReturn
+    }
+
     /// ✅ SMART refresh (uses cache)
     @objc func refreshOutdatedList() {
         // if fetched in last 5s → uses cache