From 2931b800749f007b8d9bc0fcce5839b2e1310618 Mon Sep 17 00:00:00 2001
From: maxsoch <maxence@socheleau.fr>
Date: Mon, 13 Jul 2026 18:58:32 +0200
Subject: [PATCH] fall back to reinstall when a cask cannot be upgraded as-is
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Self-updating apps (Zen, Chrome, …) drift from what brew installed;
brew then refuses to upgrade the cask in place, prints a warning and
does nothing, so the package stayed outdated forever. Detect the
warning and run the fix brew itself suggests (reinstall --cask
--force). Single-package upgrades now also route casks through
upgrade --cask instead of a bare brew upgrade.

Co-Authored-By: Claude Fable 5 <noreply@anthropic.com>
---
 BrewBar/BrewBarApp.swift | 32 ++++++++++++++++++++++++++++----
 1 file changed, 28 insertions(+), 4 deletions(-)

diff --git a/BrewBar/BrewBarApp.swift b/BrewBar/BrewBarApp.swift
index 27f9255..45e2a19 100644
--- a/BrewBar/BrewBarApp.swift
+++ b/BrewBar/BrewBarApp.swift
@@ -368,12 +368,28 @@ class AppDelegate: NSObject, NSApplicationDelegate {
         }
 
         statusMenuItem.title = "Upgrading \(next)..."
-        // an explicitly named cask upgrades even when self-updating, no --greedy needed
-        runBrew("upgrade --cask \(next)", askpassMessage: "upgrade \(next)") { _, _ in
+        upgradeCask(next) {
             self.upgradeCasksSequentially(Array(names.dropFirst()), completion: completion)
         }
     }
 
+    /// Self-updating apps (Zen, Chrome, …) can drift from what brew
+    /// installed, and brew then refuses to upgrade the cask in place —
+    /// it only prints a warning naming the fix. Run that fix for it.
+    /// (An explicitly named cask upgrades even when self-updating, no
+    /// --greedy needed.)
+    func upgradeCask(_ name: String, completion: @escaping () -> Void) {
+        runBrew("upgrade --cask \(name)", askpassMessage: "upgrade \(name)") { output, _ in
+            guard output.contains("cannot be upgraded as-is") else {
+                completion()
+                return
+            }
+            self.runBrew("reinstall --cask --force \(name)", askpassMessage: "reinstall \(name)") { _, _ in
+                completion()
+            }
+        }
+    }
+
     func confirmUpgrade(formulae: Bool, casks: Bool) -> Bool {
         let packages = (formulae ? cachedOutdated.formulae : []) + (casks ? cachedOutdated.casks : [])
 
@@ -524,13 +540,21 @@ class AppDelegate: NSObject, NSApplicationDelegate {
     }
 
     @objc func upgradeSingle(_ sender: NSMenuItem) {
-        guard let formula = sender.representedObject as? String else { return }
+        guard let name = sender.representedObject as? String else { return }
 
-        runBrew("upgrade \(formula)", askpassMessage: "upgrade \(formula)") { _, _ in
+        let finish = {
             self.cleanupAfterUpgradeIfEnabled {
                 self.refreshAll()
             }
         }
+
+        // casks go through upgradeCask for the reinstall fallback; a bare
+        // "brew upgrade <name>" would hit the same warning and do nothing
+        if cachedOutdated.casks.contains(where: { $0.name == name }) {
+            upgradeCask(name, completion: finish)
+        } else {
+            runBrew("upgrade \(name)", askpassMessage: "upgrade \(name)") { _, _ in finish() }
+        }
     }
 
     /// Refreshing offline would silently succeed on stale data: brew update