So long as you make sure you are reminting your SERVER CERT and not the CA Cert, the process is normally painless and will rarely causes issues.

Reminder: ZCM 20.2 is way out of date.....ZCM 23.4 is a relatively simple update on the server side has provides LTS and still supported WIndows Servers if that is holding you back.

Thanks, Craig, ha ha ha, for sure I will make sure I hit the right button :)  Yeah I know I'm out of date, I want to go to 24.4 this summer or a little earlier. I was looking at the upgrade path just yesterday actually and planning. The only thing I always struggle with, is I never seem to get a clean install of the ZENworks client on upgrade. I have tried both letting the system roll out the upgrade in waves and also with your amazing help, we created a custom, install. I would say the custom install was 60% effective but there were client that looked like they were fine, but they were not working correctly, so I ended up ripping those ones out and doing a reinstall. If I can find a way to be more effective with an Automated upgrade of the ZENworks client, I would have done the upgrade of the server yesterday :)  

Do you have any thoughts about 24.4?  Should I wait on that and just go 23.4? Thanks in advance.

I would recommend upgrading the Primary to 23.3 and then 24.4....

Then work at upgrading the Agents.

#1 - There are quite a few 23.4 Agent patches and they are not cumulative, so its harder than it should be to get them all integrated.  Server updates are cumulative so that's easy.  There are few if any 24.4 agent patches so that is simpler.

#2 - 24.4 will get fixes before 23.4 and there is a chance some fixes may not flow back though all highly important ones should.

#3 - The 23.4 to 24.4 upgrade should be painless and simple.

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Not really sure why you struggle with Agent upgrades...in general they tend to work fairly easily...if you have issues when trying to update...we can deal with that then....

Thanks Craig. I appreciate your feedback. I don't know why I struggle either with the agent updates after an upgrade, but the reality is, I do, I just seem to have bad luck with them. THat being said, the community has always been very helpful. I know I am not the only one who has issues with agent updates after the upgrade. A clean install of the client works like a hot damn, and will work until the cows come home, but inevitable agent updates seem to fail. Some succeed, but inevitably, some fail.