Hi @Jay Burgess ,
Welcome to our forum! From your description, after you restart the Outlook last week, Outlook Macro is no longer working automatically, right?
Did you change the macro security in File > Options > Trust Center? If you have set to allow all macros, but it still doesn't work, it is recommended you try to leave your macro security setting to only allow self-sign certificate Macros,
If you untick the Apply macro security settings to installed add-ins option, does that make a difference?
If above doesn't help, the issue may be more related macros. To solve it better, you can post under “Office Development “, so that more developer experts can provide you with more targeted help.
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