diff --git a/BrewBar/BrewBarApp.swift b/BrewBar/BrewBarApp.swift
index ce7fb7b..0499a28 100644
--- a/BrewBar/BrewBarApp.swift
+++ b/BrewBar/BrewBarApp.swift
@@ -225,15 +225,39 @@ class AppDelegate: NSObject, NSApplicationDelegate {
 
         statusMenuItem.title = "Upgrading..."
 
-        // must match the outdated listing: greedy-listed casks are skipped by
-        // plain "upgrade" and would stay outdated forever
-        let command = Settings.includeGreedyCasks ? "upgrade --greedy" : "upgrade"
-
         runBrew("update") { _ in
-            self.runBrew(command) { _ in
-                // everything was just upgraded; don't chain an auto-upgrade
-                self.fetchOutdated(allowAutoUpgrade: false)
+            // packages that turn outdated only after this brew update are not
+            // in cachedOutdated yet; the final refetch will surface them
+            let caskNames = self.cachedOutdated.casks.map(\.name)
+            let upgradeCasksThenRefresh = {
+                self.upgradeCasksSequentially(caskNames) {
+                    // everything was just upgraded; don't chain an auto-upgrade
+                    self.fetchOutdated(allowAutoUpgrade: false)
+                }
             }
+
+            if self.cachedOutdated.formulae.isEmpty {
+                upgradeCasksThenRefresh()
+            } else {
+                self.runBrew("upgrade --formula") { _ in
+                    upgradeCasksThenRefresh()
+                }
+            }
+        }
+    }
+
+    /// Upgrades casks one at a time so each sudo prompt can name the app it
+    /// is for — a batched "upgrade --cask" gives no per-package hook.
+    func upgradeCasksSequentially(_ names: [String], completion: @escaping () -> Void) {
+        guard let next = names.first else {
+            completion()
+            return
+        }
+
+        statusMenuItem.title = "Upgrading \(next)..."
+        // an explicitly named cask upgrades even when self-updating, no --greedy needed
+        runBrew("upgrade --cask \(next)", askpassMessage: "upgrade \(next)") { _ in
+            self.upgradeCasksSequentially(Array(names.dropFirst()), completion: completion)
         }
     }
 
@@ -321,13 +345,9 @@ class AppDelegate: NSObject, NSApplicationDelegate {
     func runAutoUpgrade(formulae: Bool, casks: Bool) {
         statusMenuItem.title = "Auto-upgrading..."
 
+        let caskNames = casks ? cachedOutdated.casks.map(\.name) : []
         let upgradeCasksThenRefresh = {
-            if casks {
-                let command = Settings.includeGreedyCasks ? "upgrade --cask --greedy" : "upgrade --cask"
-                self.runBrew(command) { _ in
-                    self.fetchOutdated(allowAutoUpgrade: false)
-                }
-            } else {
+            self.upgradeCasksSequentially(caskNames) {
                 self.fetchOutdated(allowAutoUpgrade: false)
             }
         }
@@ -372,7 +392,7 @@ class AppDelegate: NSObject, NSApplicationDelegate {
     @objc func upgradeSingle(_ sender: NSMenuItem) {
         guard let formula = sender.representedObject as? String else { return }
 
-        runBrew("upgrade \(formula)") { _ in
+        runBrew("upgrade \(formula)", askpassMessage: "upgrade \(formula)") { _ in
             self.refreshAll()
         }
     }