IT/Tech: Upgrading from Exchange 2013 to Exchange 2016... a first experience


As an early adopter - who admittedly I am - I played around with Exchange 2016 previews over time. However, I left the production system Exchange 2013 CU 8 since it worked pretty well, and over playing around with Exchange 2016 I kind of oversaw Exchange 2013 meanwhile got CU 9 and CU 10.

Since I didn't find any good how-to for upgrading from 2013 to 2016, and since I didn't want to go through the entire chain in my virtual playground, I decided to upgrade the less hurting production system to Exchange 2016. Despite I obviously ignored the work of the Technet team and their Exchange 2016 article chain. Of course I should have read through several of the Exchange Team Blog articles by now as well ;x)

RTFM is really a good idea... but as I said, this is going to be a hands-on - not recommended - installation description, serious but unconventional and only good if you just harm yourself if it doesn't work out ;)

This is what I experienced the way down the road.

A blind start

I know, I know, never do something without having others experienced all the problems... but since I am seasoned in terms of Microsoft products and problems and more than this - I am not a full time admin and the worse I could kill is my own, private production system, I thought in my spare time playing around is not the worse to do - so others can see what might happen, or not...

After extracting the ISO and than extracting the EXE the first surprise was that Exchange 2016 felt like installing Exchange CU XYZ, despite the first surprise was that it told me to install CU 10 minimal for Exchange 2013 server. I can remember that I read during the beta phase something like CU 8 is minimum... well, since I can not find this article anymore, it might be fiction anyways.

First learning: Exchange 2013 CU 10 is minimal requirement for installing Exchange 2016. Which can be downloaded directly from Microsoft.

I am not going into the installation of Exchange 2013 CU 10 because I am sure most of you did install a number of CU's before. And as I guess, most of you asked themselves for the thousands of thousands of time why the heck the installation wizard developers couldn't make this "Readiness Checks" at the beginning of the installation instead ages later... the classical:
Error: A reboot from a previous installation is pending. Please restart the system and then rerun Setup. For more information, visit: http://technet.microsoft.com/library(EXCHG.150)/ms.exch.setupreadiness.RebootPending.aspxappeared in my case... no need to mention that this did cost already 10 min on my machine AND more important, it will cost 10 more minutes after reboot... and yes, this time it was my fault, I did have a real reboot pending I forgot :|

However, if you are sure you don't need it, just read the article mentioned in the error message and just delete the registry entries (on your own risk, of course). From my experience, the retry is working without any reboot necessary after registry change.
A short note to Microsoft: PLEASE change this behavior.. in all your wizards, it's annoying and not everyone is running your servers on super-high-end-high-speed machines as you may noticed already ;o)

The Exchange 2016 installation

After installation Exchange 2013 CU 10... which took ages on my machine I finally can start Exchange 2016 installation. As mentioned, I extracted the ISO and the EXE meanwhile.

Well, well, well... I should have read the error messages entirely when I started the Exchange 2016 setup first time ... you won't believe it but you can't do an In-Place upgrade :x - Am I taken wrong or was this possible so far - it's a long time ago I upgraded Exchange 2010 to Exchange 2013.
As a matter of fact, no one can say the Microsoft developers have no fun at work... the retry button (see blue circle above) in this dialog is cynical, isn't it - I wonder if they trace how often one is clicking on it in the here given situation ;)

And again: Why can't the Readiness check be done in first place - on my machine, this took again about 15 minutes... 

Exchange 2016 installation - 3rd approach :(

Admitted - one approach is on me since I missed to read the Readiness Check Errors all together.. I should have done so. However, now let's summarize the current situation so far.
  • Exchange CU 10 is the minimal version Exchange 2013 has to have to be upgraded.
  • DO NOT try to do an In-Place upgrade.
  • Microsoft should place the Readiness Check to the beginning of the Wizard, not in the middle of no-where !
 more to come as soon as I proceed... now first I've to find a system I can continue on :(
Since I am either to stupid to search the right way to find information about how to upgrade to Exchange 2016 from Exchange 2013... I'll give up for the moment.
As it looks by now, the upgrade path is to install Exchange 2016 on a separate machine and than move the mailboxes... I neither found something about this nor tried it so far, however - that's going to be what I'll try to do over this weekend (CW 40). If there is no one until than telling me a better way.

I did decide to setup a Virtual machine - however, the running gag with the Readiness Checks is ongoing:
If I would have read on below the Powershell part in the mailbox server prerequisites section, I might would have saved again some time by recognizing the two links mentioning .NET Framwork 4.5.2 and Microsoft Unified Communication API 4.0, Core Runtime 64-bit which of course! need to be installed prior to the Exchange 2016 installation... 
Conclusion: Either you give yourself the time or you better don´t install Exchange 2016 while you are working on important stuff... or in short: This article shows how to NOT do it in production environments...
 At least, you do not need to do my mistakes - if you read before act ;-)

After the installation of .NET 4.5.2 (first, it was the first in order and I didn´t want to loose even more time so guessed) and the Unified Communication API, I finally hope for the best and start - again - my Exchange 2016 Server attempt.

The good news, installation is fast and no reboot is needed (whew). And I just found out, here, the retry button is no joke, you can install both preliminaries without stopping the Exchange 2016 installation.

A sign of light:

And since I did want to install everything with the help of the Wizard, thank you Microsoft for doing this for me (bow). I hope it is working out... Since I am running everything of Hyper-V, I see that the main AD-Controller is also under stress - and the progress bar is moving... yep, that´s looking good, very good... and the installation is working. The AD is prepared and Exchange 2013 still working? Yes - again good news.

Meanwhile the setup went through, no further problems - great... I now try to login as Domain Administrator... this looks good as well... interesting side note: I updated the new Windows Server 2012 R2 installation entirely before I started the installation of Exchange 2016 - now the Windows Update Routine finds another 11 mandatory and 2 optional updates... well I'll go for them and than let's see what happens.

As of by now, Exchange 2016 calls itself Version 15.1 (Build 225.42), while my parallel Exchange 2013 installation after CU 10 calls itself Version 15.0 (Build 1130.7)... I'll check and potentially write about further findings either in this article as an update or nothing. I am sure the specialized resources in the net will soon come up with better, more detailed and way more helpful articles than this one.

I'll than try to install Exchange 2016 'the right' way and see if this takes on the same Hyper-V server also ages.

Last and least I am still seeking a solution for an in place update - I can not think about (many) arguments speaking against it. And not everyone is - as I am are - ridiculous enough to run Exchange in Hyper-V even for many people, not for a view 8-)

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