Question RE Upgrading SmarterMail Server OS
Question asked by Steve Vibert - 11/22/2019 at 11:04 AM
Answered
We're currently running SM 15.7 on a Windows Server 2008 R2 box.  We're planning on doing an in-place upgrade to Windows Server 2012 R2.  We will, of course, do a full backup before doing the Window upgrade but are there any gotchas we should be aware of before starting?  

Thanks -- Steve

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Michael Smith Replied
If i was you, I would migrate sm 15 into a different server with 2012 r2/ (2016 if posible) instead of doing a upgrade in place. you will save a lot time and avoid tons of pain.

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Matt Petty Replied
Employee Post Marked As Answer
Since you are going to do a full windows backup before your upgrade, I suggest an in place upgrade. This ensures no files get lost in a move. Doing it in place ensures that it has all the files it needs. A conversion process will run when you move off of 15, it should be quite fast.
You can view the status of the conversion and any reported issues @ http://<yourSMurl>/interface/convert-status

I've seen issues where someone moved a partial set of files over and it caused many issues with the new set of data. The only hope was to go back to the backup, verify everything moved, then had to retry the conversion.
Matt Petty
Software Developer
SmarterTools Inc.
(877) 357-6278
www.smartertools.com
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Jade D Replied
We've successfully upgraded Windows 2008 R2 to Windows Server 2012 R2 and then up to Server 2016 with MS SQL services installed, and had no issues.

Anyone who works with SQL will no that its a pain in the ass on a good day so an upgrade without any issues is a win.

Best suggestion is to convert your physical machine to a virtual, and then test - thats the only way you discover any issues.
Smartermail 15 will run fine on server 2012 R2 so theres no reason to be concerned about Smartermail - Just make sure that Mail services are stopped at the time of upgrade - I would also stop IIS.
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Steve Vibert Replied
We ended up doing an in-place OS upgrade and SM didn't skip a beat despite some not so smooth MS related upgrade woes.  Namely, an odd .net framework 4.5.2 update that took down our Sitefinity CMS until we reinstalled the update and TLS 1.2 issues that took hours of googling to find the obscure registry value required by 2012 R2 to actually use TLS 1.2 even though it was enabled and TLS 1.0 and 1.1 were disabled. 

SM kept humming along despite both of these "you gotta be shi***** me!" issues.

Thanks for all of the suggestions -- Steve

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