Server Essentials 2016 hasn't installed updates in months.

This issue appears to have started around mid-February. Would it be worthwhile to try to recover the registry from the February backup and attempt to export these specific keys using an offline registry viewer?
 
Step 1:
Warning: This script was written specifically for this user, for use on that particular machine. Do not run this script on another machine.

Download the attachment and extract it.
Open the extracted folder, double-click the file regfix.reg.
When prompted allow to change the registry settings.
Report the result.

Step 2:
Restart the machine.
Check Windows Update again and report the result.
Copy the files C:\Windows\logs\cbs\cbs.log and C:\Windows\logs\dism\dism.log to your desktop.
Zip the copied files and attach the zipfile to your next reply.

Step 3:
Would it be worthwhile to try to recover the registry from the February backup and attempt to export these specific keys using an offline registry viewer?
Yes. Provide a copy of the SOFTWARE hive from that backup so I can have a look at it first.
Extract the file C:\Windows\System32\Config\SOFTWARE (no extension) from the backup and zip it.
Then upload the zip file (SOFTWARE.zip) to a file sharing website. Examples of services to upload to are Gofile or WeTransfer.
Note: Send the downloadlink in a private message as the SOFTWARE hive contains sensitive information!
 

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