diff --git a/BrewBar/BrewBarApp.swift b/BrewBar/BrewBarApp.swift
index df5552f..3024413 100644
--- a/BrewBar/BrewBarApp.swift
+++ b/BrewBar/BrewBarApp.swift
@@ -216,8 +216,12 @@ 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+        // must match the outdated listing: greedy-listed casks are skipped by
+        // plain "upgrade" and would stay outdated forever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("upgrade") { _ in
+            self.runBrew(command) { _ in
                 // everything was just upgraded; don't chain an auto-upgrade
                 self.fetchOutdated(allowAutoUpgrade: false)
             }