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pkg not installed in Jail after upgrade from 12.2 to 13.0

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I just upgraded Truenas to 13.1. After doing so I ran the iocage upgrade for all my jails. All worked well except my Plex jail. Plex is up and running, but I can't update any pkgs.

Here is the errors I get, seems to be an issue with certificates, but I am not sure how to resolve:
Code:
root@plexmediaserver-plexpass:~ # pkg update
The package management tool is not yet installed on your system.
Do you want to fetch and install it now? [y/N]: y
Bootstrapping pkg from...


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