Hi headrush1111,
In terms of the issue only occurred on Outlook client and it worked smoothly on Outlook Web App. The issue should be caused by a client side issue. Based on the situation, I suggest repairing the user’s Office installation to see if any progresses. The following steps are for your reference.
1. Click Start > Control Panel > Programs and Features.
2. Click the Office program you want to repair, and then click Change.
3. Click Repair > Continue. You might need to restart your computer after the repair is complete.
Thanks,
Maggie Li