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Errors with Cloud, mobile App and, default_config after upgrade

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I know it’s not the most popular way to run home assistant, but I’m running in an iocage jail on TrueNAS (formerly FreeNAS)

I just upgrade from 118.5 to the new 2020.12.1, which also required upgrading from Python 3.7 to Python 3.8.

When all was said and done, most things work fine locally, but there are some oddities with the Android app when on the home network, and homeassistant cloud / nabucasa is down hard.

I believe the error that is causing the problem is here:

 Logger: homeassistant.setup
 Source: setup.py:138
 First occurred: 8:00:21 PM (3 occurrences)
 Last logged: 8:00:26 PM
 
 * Setup failed for cloud: Unable to import component: /srv/homeassistant/lib/python3.8/site-packages/cryptography/hazmat/bindings/_openssl.abi3.so: Undefined symbol "sk_pop_free"
 * Setup failed for mobile_app: Unable to import component: /srv/homeassistant/lib/python3.8/site-packages/cryptography/hazmat/bindings/_openssl.abi3.so: Undefined symbol "sk_pop_free"
 * Setup failed for default_config: Could not set up all dependencies.

Looks to be ssl related, but I have no idea where to go from here.

Thoughts?

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