Our printed printed a bunch of labels over the weekend and after checking our system, it looks like all these labels came from print jobs that originally through a timeout error: 

Failed to run the Print Command Script action. Details: This request operation sent to [Server] did not receive a reply within the configured timeout (00:01:00).  The time allotted to this operation may have been a portion of a longer timeout.  This may be because the service is still processing the operation or because the service was unable to send a reply message.  Please consider increasing the operation timeout (by casting the channel/proxy to IContextChannel and setting the OperationTimeout property) and ensure that the service is able to connect to the client.

Looking back in the history, there appears to have been a failed print job with that status message on 9/23. Everything after that picked up the same status message, even though it printed successfully at that time. Then, checking in the Reprint console on the server, I can see all of these queue (or sent) print jobs that happened over the weekend. The number of them matches with the number of print jobs since that error started appearing. 

I want to understand what happened here so I can prevent this in the future. Why did the print job information for these hundreds of jobs still exist, where was it stored, and why did a server restart cause them to be added into the print queue?