Hi @Robert Mallett ,
Welcome! Firstly, sorry for the inconvenience Outlook brings to you.
Before going further, what's the version of your Outlook? (File > Office Account > About Outlook). In order to avoid troubles from version-related issues, please make sure you have upgraded your Outlook to the latest version.
And does this not working issue only happen to these specific Outlook rules? Can other Outlook rules in your Outlook client work fine?
Here is some common used troubleshooting methods about Outlook rule issue, please check the suggestions in this article Rules do not work automatically and see if they could help resolve your issue. (Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.)
By the way, since you are using Exchange email account, Outlook rules can also be synced between your Outlook client and mail server. If the issue still continues, please try remove all your Outlook rules from your Outlook client and re-create them from your web mail. Then restart your Outlook client and wait for the sync to check if it could help.
Hope this can be helpful.
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