Mac thinks my System Extensions are kernel extensions

I ran into a strange problem during development this morning. When trying to install my Endpoint and Network System Extensions (something I was able to do yesterday, and many times before), my Mac is prompting me to enable Kernel Extensions.

Right before this happened, I had problems deleting the previous version of the apps from the /Applications folder (it took many tries). This too was unusual.

After agreeing to allow the installation of my Endpoint System Extension, I was greeted with this previously unseen message and button:

When I click "Enable System Extensions...", and I am greeted with this alert:

I also ran into this problem when trying to install my Network System Extension.

Anyone have any idea how I screwed up my system?

Anyone know how to return it to normal behavior?

System: Mac Studio 2022
OS: Ventura 13.4.1

(I'm thinking of re-instaling Ventura this evening; would prefer not to)

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I think the problem was a combination of certificates expiring and registered devices expiring. Once I corrected these, installation of Endpoint System Extensions started working again.

Note: I had multiple certificates generated on multiple Macs (that I actively use), which expired at different times. I think this created a rolling set of failures over a span of about a week. Development stopped working on one machine but not another. Eventually everything stopped working. It was very confusing for me at the time.

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I think the problem was a combination of certificates expiring and registered devices expiring. Once I corrected these, installation of Endpoint System Extensions started working again.

Note: I had multiple certificates generated on multiple Macs (that I actively use), which expired at different times. I think this created a rolling set of failures over a span of about a week. Development stopped working on one machine but not another. Eventually everything stopped working. It was very confusing for me at the time.

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Todd_at_Ennetix
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