Hi @Thomas Faherty ,
Could we know that there is the MP or SUP role in the DMZ? In our environment, it is recommended to install a new site server that has MP/DP/SUP roles for your test servers to take more flexible management.
Here is the article about the best practice of deploying updates patch in DMZ server:
https://social.technet.microsoft.com/Forums/office/en-US/921bc8c2-e8b6-4f78-af1a-b589edd8b163/the-best-practice-of-deploying-updates-patch-in-dmz-server-quotsccm-wsus-quot?forum=configmanagergeneral
If it exists already, we could try to connect the DMZ MP to check if it is normal and there is any error in these logs.
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