pfSense OpenVPN Clint Export issues & upgrade

I have a Netgate XG-7100 on 2.4.4-RELEASE-p3 with about 12-15 users connecting. Some some of them have a weird connection issue. They try to connect, but never get the “Successfully Connected” pop up & just have a yellow connection icon. In the pfSense dashboard I do see them as connected.
Here’s the error it shows:

Tue Mar 31 12:46:28 2020 Initialization Sequence Completed With Errors ( see )

However if they do an uninstall & reinstall of the same client .exe installer it works perfectly fine on the second installation. The DHCP Client doesn’t seem to the the issues, since re-installing fixes it.

I noticed my OpenVPN Client Export tool was out of date. I’m on 1.4.18_4 & 1.4.20 is out. If I update it, will it break all of the existing clients? And will I need to re-deploy to everyone?

Updating the export client will not break the existing installs as that is just the tool that generates the installer. The update is for version and bug fixes, so make sure you are keeping that part up to date.