Migrating JSS to Windows Server 2019

@aamjohns I am not on Windows Server 2019, but 2016 works fine. Also, is version 10 working on 2008R2? Have lots of un-used 2008R2 VMs.

@jared_f Hi,
We want to go to 2019 to postpone the eventual expiration of the OS for as long as possible. Yes, it is working fine for me on 2008R2. 2008R2 will be unsupported Jan. 14th 2020.

Thanks,
AJ

@aamjohns Let me ask around, we probably have a Windows Server 2019 VM I can sandbox in. If Jamf can run on 2016 I am pretty confident it can run on 2019. They aren't that different.

@jared_f ,
I agree with your logic. They are not that different. As long as certain prerequisites (.Net and C++ runtime) are in place I would imagine it will work. But, I cannot move forward without confirmation. I've also reached out to our Jamf A.S. to see if there is an official word from JAMF. I don't want to install it on something that is not supported.

When I checked MySQL it too does not list server 2019 as supported. It may be just a timing thing since 2019 is pretty new.

Thanks,
AJ

As a follow up, I have migrated our JSS from MS Server 2008R2 to MS Server 2019 without issue. So far it seems to be running fine.

Thanks,
AJ

@aamjohns Do you have some more info about your migration process?
I guess, you just exported and re-imported the whole MySQL db from the old server to the new one?

We are also in the process of migrating our old JSS (2008R2) to a new MS Server 2016, but we don't want to import the old DB whenever possible. We want to re-enroll the existing Mac devices to the new server only, so we have a prober DB as starting point.

@aamjohns @hansjoerg.watzl

We're also interested in the migration process. I'm taking the Jamf 400 class to help with the education part just in case. I've also never migrated JSS Servers. We are using Apple boxes/servers.

Might want to hold off. Jamf Pro is not officially supported on Server 2019 yet so if you have an issue you might not be able to get Jamf to help much. Source

@hansjoerg.watzl,
I prepared the server with the prerequisites. After that I did the install. Then I exported and imported the db. After that I shutdown the old server, renamed the new server to the old name, and assigned the same IP config. I exported the certificates from the old to the new. All of that worked fine. One thing that I ran into an issue with was getting the IIS on the new server working properly for using an http distribution point. Until I found on here where someone posted about adding mime types for the Mac file extension it wouldn't work as a DP. After adding the mime types, it worked.

Also,

Thanks for you info. Unfortunately we can't re-use the same hostname, JSS URL and certificates from our old server, so it seems much more complicated than your scenario. Hopefully Jamf will assist us (we already opened a support case).
Interesting about the Mime types for your DP. We also configured a DP with IIS on our new (not productive) server and it worked without mime types. (But for the reposado installation on the same server, we needed to add several mime types for the reposado html folder)

@aamjohns Im getting ready to do the same migration that you did. Im going from Windows Server 2008R2 to Windows Server 2019. I installed and configured Java 11, MySQL 8 and created the database. I installed Jamf Pro 10.14 and connected to the database. I setup IIS with the MIME types according to the article "Using IIS to Enable HTTPS Downloads..." and some other configurations on the new server.

I have several questions. Jamf support pointed me to a couple of documents that dont cover everything and are outdated. One of them mentions restoring the database with the Jamf Pro Database Utility but that was discontinued with 10.14 and you need to use the Jamf Pro Server Tools.

They mention backing up the database and restoring it to the new server. Does the version of Jamf Pro need to be the same on both servers? Im going from 10.13.1 to 10.14. If I migrate the database, is there any need to run the Jamf Migrator tool? Does the database restore move over the DEP, VPP and APNS tokens or do they need to be re-created? Im assuming all the contents of the Distribution point need to be copied over?

I wasnt planning on using the same names but rather change the DNS entry to point everything to the new server.

@msnowdon Hello. I cannot actually answer all of your questions with certainty.

--Im going from 10.13.1 to 10.14 -> I'd just try it. My guess is it will work. Yes, use the new server tools for this.
Thanks for calling my attention to https://github.com/jamf/JamfMigrator. I was not aware of that tool. Looking at it, I'd say you don't have to use it, but can use it if you choose. As it says granular migration so it lets you choose what to bring over.
I don't know about DEP and VPP since we don't use that but I would guess yes they will come over. If I remember correctly, my APN certificate migrated.

As long as your server name stays the same but you update the dns, your clients should remain enrolled. Mine did. I set my new server up with a different name and then when I had it ready, I took down the production server, renamed the new server to the 'old' name, and updated the dns.

For the distribution point, I copied over the contents to an identically named share on the new server and that worked fine. I did have to get a new certificate for IIS.

I'd say export and import your db, and see what you get. Create an identical share on the new server and copy from old to new. To me it is worth trying and benefitting from what works and if it doesn't you can always upgrade your existing to the same version and re do the export import of the db. See if your DEP and VPP come over. Maybe post back with your results so others may benefit. Thanks, AJ