Al1en_Zach
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Al1en_Zach's post in Wireguard VPN Tunneled Access for Docker was marked as the answerSomeone on Reddit was able to help me with this.
My server key had expired. I'm not sure for other services, but for ProtonVPN, they last a year.
Be sure to toggle old connection to "Inactive" if adding a new connection for your docker containers, this may interfere. It did for me when I realized new and old server were using same Peer Endpoint IPs.
Hope this helps someone!