Dear @TJ Garland,
Based on the issue message you shared, this appears to match a recently reported issue affecting certain New Outlook for Windows builds, where olk.exe may fail to start with a TryCreatePackageDependency entry point error in Microsoft.Windows.Workloads.dll.
As Quick Repair did not resolve the issue, I recommend fully uninstalling New Outlook for Windows, then reinstalling it from the Microsoft Store.
Also, you can try this step before reinstalling:
Press Windows + R > run: %LocalAppData%\Microsoft
Delete the folders: Olk, OneAuth
Then restart Windows.
If the issue continues after these steps, using Classic Outlook or Outlook on the web temporarily may be the most practical workaround until a corrected update becomes available.
There are some similar cases having same issue as you:
I sincerely apologize for this inconvenience and thank you for your understanding.
I hope the information shared helps point you in the right direction. Please try the steps above and let me know if they work. If not, we can continue working together to narrow this down.
The first response may not always resolve the issue right away, but with your help and more details, we can work toward a solution.
As a moderator, I do not have the tools to investigate your specific account directly, as this is a support forum between users. Moderators and collaborators, including external Microsoft employees, may not directly intervene in the functionality of Microsoft products or access internal systems. Our role is limited to providing technical guidance on reported problems, requests, or ideas. However, I will do my best to guide you as clearly as possible.
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