Hi @Matt Stiller !
Activities should sync using the timezone you're using to create them in Pipedrive, and show up in your external calendar having been converted to its timezone. Is your Outlook Calendar using UTC as default?
This seems like a more technical case, so I recommend you reach out to our Support team and they will help you with any necessary troubleshooting.
See here how to get in contact: https://support.pipedrive.com/hc/en-us/articles/115005875565-How-can-I-contact-Pipedrive-Support-
This same issue is occurring for me as well. Is there a knowledge base on how to correct?