First, I would like to say that I am an educational technologist providing level 3 support (server-related queries) for our Moodle site, but I am not a network technicians
I have worked with Ubuntu servers in the past, but it is the first time that I work with a Windows server.
Our main production site is installed in a virtual machine which runs in Windows Server 2008 R2 Enterprise (no additional service package have been installed).
There haven't been any updates installed since the senior technician left the project in November 2011, and since I took over the maintenance, I didn't receive any automatic notifications telling me that important updates need to be installed.
I was busy migration to Moodle 2.24 over the summer, but now that I have time to familiary with Windows server, I have discovered that there are 68 important updates ready to be installed and 32 optional updates.
When I looked the information about those updates, it seems that most of the important updates are security updates for Windows (and .NET) and the optional updates are related to upgrading the Windows server OS (installing package services and so on).
Should I install the 68 important updates or leave Windows as it is now?
We have an anti-virus software and a proxy, so I think that the server is quite secure without the upodates.
If this were a Linux server, I would install the updates, but I don't trust Windows at all. I am concerned that, by installing any of the updates, the performance of our production site will be affected or any of the php or MySQL settings will be also affected.
Can you please advise about this matter?
Thank you very much for your advise.