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Upgrade OS from Server 2008 to 2016 - issues

Question asked by Paul LaFollette on Nov 27, 2018
Latest reply on Dec 30, 2019 by Richard Post

Our Uniprint system has two servers that are running Windows Server 2008 R2, and two servers that are running Windows Server 2012 R2.  I'd like to bring them up to Windows Server 2016 (with minimal downtime, of course).  What are some issues I might run into?


The way I see it, I have two choices.

  • Build new/clean systems running Server 2016, and migrate our Uniprint systems and settings to the new systems.  When complete, shutdown the old systems and bring the new systems online in their place.
  • In-place upgrade, by upgrading the OS of the existing systems, with everything (the Uniprint systems) already on the systems.


The first choice would most likely provide the cleanest and most optimal end result (assuming we get everything correct and don't forget or mess up anything), but it would be the most "painful" and time consuming to perform as we would be essentially building from scratch the new systems, installing from scratch the Uniprint systems, followed by migrating settings and objects from the old to new systems.  The second choice is tempting because it would require the least amount of time, the Uniprint systems would not have to be reinstalled (if everything survives the OS upgrades), only requiring the OS to be upgraded.


If I go with simply upgrading the OS, what issues might I run into?


I'm told upgrading from Server 2008 R2 to Server 2016 would require upgrading from 2008 R2 to 2012 R2 followed by upgrading to 2016 (if all goes well).  I'm told IIS has a tendency to "break" when going from 2008 R2 to 2012 R2, however upgrading from 2012 R2 to 2016 may go relatively painless.


Any recommendations/suggestions are welcome.


Our current configuration is like this:

  • Server 1 - Windows Server 2008 R2 - hosts the "primary" Uniprint system, Print Center, Database Service (database is on an SQL server), Popup Server, EDI Service, Online Service Client, serves close to 50 print queues.  Of the 50 queues, 6 of the queues handle nearly all of the Student printing (which is about 1/2 of all our printing).
  • Server 2 - Windows Server 2008 R2 - hosts the "secondary" Uniprint system, serves about 733 print queues.  Handles about 1/2 of all our printing (almost all Direct Printing).
  • Server 3 - Windows Server 2012 R2 - hosts Mobile Print.  Has 4 "renderer" printers defined.  Currently, Mobile Print jobs account for 60% of all printing by our Students.
  • Server 4 - Windows Server 2012 R2 - hosts the "outward facing" interface for Print Center



- Paul L.