Hi @Darcy Morgenstern ，
Welcome to our forum!
When I schedule a Teams meetings via my outlook calendar, it does not populate onto my Teams calendar
What's the type of your account?
And what's the version of your Outlook and teams client(file>office account>about outlook), please first ensure that you have updataed to the latest version of client.
I have tried to use my Microsoft 365 account to create a teams meeting on Outlook 365 for testing, and found the meeting could be displayed normally on my Teams calendar, it seems that there may be any sync errors between your Outlook and Teams. In order to further confirm whether the issue is related to your Outlook or Teams, it's suggested to log in your web mail and web teams to check if you could find the Teams meetings created in your Outlook client there, if so, the issue may be related to your Teams client.
For synchronization issues in teams, it's suggested to first log out your account, exist teams via task bar then restart it and re-login the account(with same account in Outlook) to check if the issue has any difference.
Also, based on my research, I foubd a related thread, which mentioned cleaning the cache may affect this issue, it's suggested to follow the steps to check if it could also work for you.
Hope your issue would be resolved soon.
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