diff --git a/scripts/release/macos/templates/azure-cli.rb.in b/scripts/release/macos/templates/azure-cli.rb.in
index 4b5e7e93385..6941ba1fe62 100644
--- a/scripts/release/macos/templates/azure-cli.rb.in
+++ b/scripts/release/macos/templates/azure-cli.rb.in
@@ -1,12 +1,12 @@
 cask "azure-cli" do
   arch arm: "arm64", intel: "x86_64"
-  os macos: "macos"
 
   version "{{ version }}"
   sha256 arm:   "{{ arm64_sha }}",
          intel: "{{ x86_64_sha }}"
 
-  url "https://github.com/{{ github_repo }}/releases/download/azure-cli-#{version}/azure-cli-#{version}-#{os}-#{arch}.tar.gz"
+  url "https://github.com/{{ github_repo }}/releases/download/azure-cli-#{version}/azure-cli-#{version}-macos-#{arch}.tar.gz",
+      verified: "github.com/{{ github_repo }}/"
   name "Azure CLI"
   desc "Microsoft Azure CLI 2.0"
   homepage "https://docs.microsoft.com/cli/azure/overview"
@@ -19,9 +19,9 @@ cask "azure-cli" do
   depends_on formula: "python@{{ python_version }}"
 
   binary "bin/az"
-  zsh_completion "completions/zsh/_az"
   bash_completion "completions/bash/az"
   fish_completion "completions/fish/az.fish"
+  zsh_completion "completions/zsh/_az"
 
   zap trash: "~/.azure"
 end
diff --git a/src/azure-cli/azure/cli/command_modules/util/custom.py b/src/azure-cli/azure/cli/command_modules/util/custom.py
index ca71e1bcaf2..c8fdfe427f3 100644
--- a/src/azure-cli/azure/cli/command_modules/util/custom.py
+++ b/src/azure-cli/azure/cli/command_modules/util/custom.py
@@ -132,9 +132,24 @@ def upgrade_version(cmd, update_all=None, yes=None, allow_preview=None):  # pyli
                 exit_code = subprocess.call(update_cmd)
         elif installer == 'HOMEBREW_CASK':
             logger.debug("Update homebrew cask")
+            # Determine cask token: 'azure-cli-preview' (custom tap) or 'azure-cli' (homebrew-cask)
+            try:
+                preview_installed = subprocess.call(['brew', 'list', '--cask', 'azure-cli-preview'],
+                                                    stdout=subprocess.DEVNULL, stderr=subprocess.DEVNULL) == 0
+                cli_installed = subprocess.call(['brew', 'list', '--cask', 'azure-cli'],
+                                                stdout=subprocess.DEVNULL, stderr=subprocess.DEVNULL) == 0
+                if preview_installed:
+                    cask_token = 'azure-cli-preview'
+                elif cli_installed:
+                    cask_token = 'azure-cli'
+                else:
+                    raise CLIError(UPGRADE_MSG)
+            except OSError as ex:
+                logger.debug("Failed to detect Homebrew cask token: %s", ex)
+                cask_token = 'azure-cli'
             exit_code = subprocess.call(['brew', 'update'])
             if exit_code == 0:
-                update_cmd = ['brew', 'upgrade', '--cask', 'azure-cli']
+                update_cmd = ['brew', 'upgrade', '--cask', cask_token]
                 logger.debug("Update azure cli with '%s'", " ".join(update_cmd))
                 exit_code = subprocess.call(update_cmd)
         elif installer == 'PIP':