Windows 10 (pre-Creator) 1607
This past weekend I installed the latest (ass|u|me it was 220.127.116.1135) from the Plex web interface and was advised today that Plex was has not been working for a few days. I went to the PC and noticed it was not in the system tray and after trying to start (it starts and quickly quits) I went to the PMS log and found it was complaining that the cacert.pem was missing. I chose to just download and reinstall Plex (AFAIK I did not see "repair") and after that it still did not work and continued to report the missing file. A search yielded a file of this name in the Python folder (outside of Plex).
I then recovered from a July 1st backup just the PMS folder and the file was there. I then went back in and found (and RECALL) that there are problems downloading/installing 1.7.5. Instead of the usual download; then install asking for higher security - it never asked. Today it kept repeating to install and never actually did it - reboot/again/reboot - still nothing - the Plex web interface repeatedly said to INSTALL and functionally did nothing.
I resorted to installing the previously downloaded full 1.7.5 and chose REPAIR - after a few moments and reboot all is fine (cacert.pem is now under Resources). Size is different than Python - similar file or not, not sure.
Curiously - the install as stated when I did it the FIRST time before going to backup did NOT install cacert.pem. Don't know what does (if starting the first time it creates or what) but clearly a re-install didn't. Is it possible the first time I was shown REPAIR and chose INSTALL? Possible but from memory I only recall 2 buttons not 3 - and then 3 after.
So a number of issues with this upgrade - thankfully I had a backup. All appears to be fine now.