If the Phish alert button doesn’t update automatically you might need to add it. To add the phish alert button the process is the same as any other add in.
In Outlook navigate to File then Manage Add-ins near the bottom. This will take you to the online portal and the popup below will come up automatically.
Click on Admin-managed and then find the Phish Alert add-in with the UW logo. Click the Add button. The button will be eventually be replaced with a checkmark indicating it has been added.
It can take several hours for the plugin to update on your system.