diff --git a/BrewBar/BrewBarApp.swift b/BrewBar/BrewBarApp.swift
index 6a071df..909b414 100644
--- a/BrewBar/BrewBarApp.swift
+++ b/BrewBar/BrewBarApp.swift
@@ -82,6 +82,12 @@ class AppDelegate: NSObject, NSApplicationDelegate {
         outdatedItem.submenu = outdatedSubmenu
         outdatedItem.isHidden = true // shown once a fetch finds outdated packages
         menu.addItem(outdatedItem)
+        menu.addItem(NSMenuItem(title: "🧹 Cleanup", action: #selector(cleanupAction), keyEquivalent: ""))
+        // isAlternate swaps this in for the item right above while ⌥ is held
+        let purgeItem = NSMenuItem(title: "🧹 Cleanup (purge cache)", action: #selector(cleanupPurgeAction), keyEquivalent: "")
+        purgeItem.keyEquivalentModifierMask = .option
+        purgeItem.isAlternate = true
+        menu.addItem(purgeItem)
         menu.addItem(NSMenuItem(title: "📜 Logs", action: #selector(showLogs), keyEquivalent: "l"))
 
         menu.addItem(NSMenuItem.separator())
@@ -271,6 +277,34 @@ class AppDelegate: NSObject, NSApplicationDelegate {
         refreshAll()
     }
 
+    @objc func cleanupAction() {
+        runCleanup(purgeCache: false)
+    }
+
+    @objc func cleanupPurgeAction() {
+        runCleanup(purgeCache: true)
+    }
+
+    /// --prune=all also deletes cached downloads brew would normally keep
+    /// (current versions); the only cost is re-downloading at next install
+    func runCleanup(purgeCache: Bool) {
+        statusMenuItem.title = "Cleaning up..."
+        runBrew(purgeCache ? "cleanup --prune=all" : "cleanup") { _, _ in
+            self.updateStatus(count: self.cachedOutdated.count)
+        }
+    }
+
+    /// Interposed between the end of an upgrade and its closing refetch;
+    /// passes straight through unless the user opted in.
+    func cleanupAfterUpgradeIfEnabled(completion: @escaping () -> Void) {
+        guard Settings.cleanupAfterUpgrade else {
+            completion()
+            return
+        }
+        statusMenuItem.title = "Cleaning up..."
+        runBrew("cleanup") { _, _ in completion() }
+    }
+
     @objc func upgradeAll() {
         if Settings.confirmBeforeUpgradeAll {
             guard confirmUpgrade() else { return }
@@ -284,8 +318,10 @@ class AppDelegate: NSObject, NSApplicationDelegate {
             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)
+                    self.cleanupAfterUpgradeIfEnabled {
+                        // everything was just upgraded; don't chain an auto-upgrade
+                        self.fetchOutdated(allowAutoUpgrade: false)
+                    }
                 }
             }
 
@@ -409,7 +445,9 @@ class AppDelegate: NSObject, NSApplicationDelegate {
         let caskNames = casks ? cachedOutdated.casks.map(\.name) : []
         let upgradeCasksThenRefresh = {
             self.upgradeCasksSequentially(caskNames) {
-                self.fetchOutdated(allowAutoUpgrade: false)
+                self.cleanupAfterUpgradeIfEnabled {
+                    self.fetchOutdated(allowAutoUpgrade: false)
+                }
             }
         }
 
@@ -454,7 +492,9 @@ class AppDelegate: NSObject, NSApplicationDelegate {
         guard let formula = sender.representedObject as? String else { return }
 
         runBrew("upgrade \(formula)", askpassMessage: "upgrade \(formula)") { _, _ in
-            self.refreshAll()
+            self.cleanupAfterUpgradeIfEnabled {
+                self.refreshAll()
+            }
         }
     }
 
diff --git a/BrewBar/Settings.swift b/BrewBar/Settings.swift
index 60ab21b..24eac13 100644
--- a/BrewBar/Settings.swift
+++ b/BrewBar/Settings.swift
@@ -44,4 +44,9 @@ enum Settings {
         get { UserDefaults.standard.bool(forKey: "confirmBeforeUpgradeAll") }
         set { UserDefaults.standard.set(newValue, forKey: "confirmBeforeUpgradeAll") }
     }
+
+    static var cleanupAfterUpgrade: Bool {
+        get { UserDefaults.standard.bool(forKey: "cleanupAfterUpgrade") }
+        set { UserDefaults.standard.set(newValue, forKey: "cleanupAfterUpgrade") }
+    }
 }
diff --git a/BrewBar/SettingsWindowController.swift b/BrewBar/SettingsWindowController.swift
index f5ad924..935abd5 100644
--- a/BrewBar/SettingsWindowController.swift
+++ b/BrewBar/SettingsWindowController.swift
@@ -22,6 +22,7 @@ class SettingsWindowController: NSWindowController {
     var notifyCheckbox: NSButton!
     var showCountCheckbox: NSButton!
     var confirmCheckbox: NSButton!
+    var cleanupCheckbox: NSButton!
 
     convenience init(appDelegate: AppDelegate) {
         let window = NSWindow(
@@ -125,6 +126,12 @@ class SettingsWindowController: NSWindowController {
             action: #selector(toggleConfirm(_:))
         )
 
+        cleanupCheckbox = NSButton(
+            checkboxWithTitle: "Run brew cleanup after upgrades",
+            target: self,
+            action: #selector(toggleCleanup(_:))
+        )
+
         let stack = NSStackView(views: [
             frequencyRow,
             customRow,
@@ -138,6 +145,7 @@ class SettingsWindowController: NSWindowController {
             notifyCheckbox,
             showCountCheckbox,
             confirmCheckbox,
+            cleanupCheckbox,
             launchAtLoginCheckbox,
         ])
         stack.orientation = .vertical
@@ -179,6 +187,7 @@ class SettingsWindowController: NSWindowController {
         notifyCheckbox.state = Settings.notifyOnNewUpdates ? .on : .off
         showCountCheckbox.state = Settings.showCountInMenuBar ? .on : .off
         confirmCheckbox.state = Settings.confirmBeforeUpgradeAll ? .on : .off
+        cleanupCheckbox.state = Settings.cleanupAfterUpgrade ? .on : .off
     }
 
     func separator() -> NSBox {
@@ -311,6 +320,10 @@ class SettingsWindowController: NSWindowController {
         Settings.confirmBeforeUpgradeAll = sender.state == .on
     }
 
+    @objc func toggleCleanup(_ sender: NSButton) {
+        Settings.cleanupAfterUpgrade = sender.state == .on
+    }
+
     @objc func toggleLaunchAtLogin(_ sender: NSButton) {
         do {
             if sender.state == .on {