[SOLVED] Please Help! Problems with Monthly Security Rollups on Windows Server 2008 R2

Update status
 

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I haven't been out to disconnect KVM, but I did remove the expired Symantec Endpoint Protection and installed BitDefender.
The newest security rollup installed and said it completed successfully (progress), but the system still boots to the recovery console.
I'm trying a chkdsk c: /f - says it repaired some usn journal entries and that the disk does not have enough space to replace bad clusters detected in file 25971 of name... but this disk has plenty of free space... do you think we are dealing with some misreported clusters (file errors) that any update is making it unbootable - until it's rolled back?
After the chkdsk completes, I suppose I will run another sfc on it and see what happens.
I just hate to roll back the update every time, as I don't think that is the root of the issue.
 
Please check the HDD with the following utility. If it's going bad then that's the root cause:

GSmartControl
Follow the instructions below to check your SMART status with GSmartControl:


  • Download the portable version of GSmartControl and save it on your Desktop;
  • Extract the zip file to your Desktop. Open the folder gsmartcontrol-1.1.3-win64 which should be located on your Desktop and double-click gsmartcontrol.exe to launch the program.
  • Identify your drive in the list (if recognized by the tool), and hover your mouse over it.
  • You should see something called: SMART status. It will either read: Enabled, in which case you should do the following:
  • Double-click on it to bring up its window (usually you'll find your drive by its size or its brand name);
  • Go to the Self-Tests tab, then select Extended Self-test in the Test type drop-down list and click on Execute (this test can take a few hours to complete);
  • Once the test is over, the results will be displayed at the bottom of the window. Please copy and paste these results in your next reply or take a screenshot;
  • Also, go in the Attributes tab and if you have any entries highlighted in red or pink, take a screenshot of the GSmartControl window and attach it in your next reply;
  • Please note: If the SMART Status reads: Unsupported, stop and let me know.
    info_failing.png
 
I don't get any options to run tests... when I double click, or click Device>View Details, I get this:

1567994130303.png
 
I may be able to take the machine down for maintenance tonight, but the MegaRAID storage manager is reporting no failures on any of the drives... so it looks like any of these issues are likely due to OS corruption.
 
Well, after weeks of dealing with this issue, just when I thought I had seen everything... Microsoft has failed at identifying one of ITS OWN problems once again!
I found an obscure mention in a vague post about security updates failing (can't even find it again now), where they mentioned stopping IIS allowed them to install these updates... and what do you know... it worked!
It turns out that this server doesn't even need IIS running at all (I didn't know, and didn't want to just start disabling services because a proprietary software developer is running a medical SQL platform on this machine and they couldn't figure out the problem either).
When you do a clean boot, and only have MS services running, and updates still fail... it's pretty obvious that it is an OS problem... not a misconfiguration, but a BUG... a FAIL on the part of MS developers to properly have the update failures generate errors or logs to properly identify an internal MICROSOFT issue. Now I see why so many are now abandoning MS products, going purely with OSX or Linux! Sure would be nice if a large group of us could get together and file a lawsuit against the software giant to regain a fraction of the billions of dollars in lost time and resources spent trying to fix their problems.
So frustrating.... But Sysnative... YOU GUYS ARE AWESOME! THANK YOU VERY MUCH for your time and effort to help me try to track this down and get it corrected! Maybe this post will save the next poor soul weeks of time and effort as well as hours, days... maybe even weeks of system downtime!!
 

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