diff --git a/modules/darwin/casks.nix b/modules/darwin/casks.nix
index 4c6fa8d..08b4dd9 100644
--- a/modules/darwin/casks.nix
+++ b/modules/darwin/casks.nix
@@ -56,7 +56,7 @@ _:
   "dbeaver-community"
   "element"
   "gpg-suite"
-  "macdown"
+  "macdown-3000"
   "mailmate"
   "orcaslicer"
   "remanager"
@@ -64,7 +64,7 @@ _:
   "smartsheet"
   "spamsieve"
 #  "sqlitestudio" # Doesn't work without Rosetta
-  "virtualbox"
+#  "virtualbox" # build error?
   "copilot-cli"
 
   # Browsers
diff --git a/modules/darwin/home-manager.nix b/modules/darwin/home-manager.nix
index 167c933..779a57f 100644
--- a/modules/darwin/home-manager.nix
+++ b/modules/darwin/home-manager.nix
@@ -33,8 +33,13 @@ in
 
   homebrew = {
     enable = true;
+    
     casks = pkgs.callPackage ./casks.nix { };
-    # onActivation.cleanup = "uninstall";
+    onActivation = {
+      cleanup = "uninstall";
+      autoUpdate = true;
+      upgrade = true;
+    };
 
     # These app IDs are from using the mas CLI app
     # mas = mac app store