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Server 2016 -> Server 2019 - Fresh install and services migrated or in place upgrade?


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Posted

Hi Guys,

 

Just wondering if anyone has experienced any issues upgrading to Server 2019 from Server 2016? I have a number of Servers that need to be upgraded including DCs, File Servers, WDS Server, SIMS etc and wondering what the best path is to do this. Would/Have you created the Servers from scratch and migrated the services/data or should I be okay upgrading over the top - ensuring I have a recent backup of course!

 

Any recommendation or advice on this would be useful.

 

Thanks

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Posted

I'm just going through a similar process except from 2012R2 to 2019.

Advice from our SIMS support company and others is to avoid an in-place upgrade if SQL is involved.

 

For us that means building new VMs for SIMS, Papercut and Biostore/Fastrak. :(

Posted

I've always done fresh installs, even on a workstation, that way you can be confident it's a good clean start.

 

If you upgrade in place, any bugs or niggles in the old setup roll forward into the new. Which then develops it's own eccentricities on top....

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Posted
I'm just going through a similar process except from 2012R2 to 2019.

Advice from our SIMS support company and others is to avoid an in-place upgrade if SQL is involved.

 

For us that means building new VMs for SIMS, Papercut and Biostore/Fastrak. :(

 

Not surprised that's the advice from SIMS support company, but there surely is no reason why it wouldn't work.

 

As has been said - just snapshot the VM first and test after.

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Posted
I've successfully in-place upgraded plenty of servers from 2012R2 and 2016 to 2019 with no issues except with an SQL server and an Exchange server, both of which failed dismally. Thank heavens for VM snapshts!
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Posted
I'm just going through a similar process except from 2012R2 to 2019.

Advice from our SIMS support company and others is to avoid an in-place upgrade if SQL is involved.

 

For us that means building new VMs for SIMS, Papercut and Biostore/Fastrak. :(

 

We've inplace upgraded with SQL, absolutely fine no issues at all.

 

Inplace upgrade is far better now than it used to be!

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Posted (edited)
....if they're VMs then snapshot them first - anything bad happens and you can easily roll back.

 

Unless it is a DC, in which case the roll-back plan must be to delete it and build a new one. A snapshot restore of a DC is nothing but pain anguish and a potential forest rebuild

 

 

Also, as well as Exchange server, you should not in-place upgrade a server with Azure AD Connect installed. If you do AADC stops auto-updating.

 

You should check the upgrade plan for each service running (NPS, DHCP, Certificate Services etc.) and make sure 3rd party software is compatible with he target version.

Edited by psydii
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Posted
I'm just going through a similar process except from 2012R2 to 2019.

Advice from our SIMS support company and others is to avoid an in-place upgrade if SQL is involved.

 

For us that means building new VMs for SIMS, Papercut and Biostore/Fastrak. :(

 

Upgrade SIMS* and Papercut no problem.

 

 

*planned this one carefully, shutdown the server before the taking the 'backup of last resort'. Powered on and then dismounted databases etc to ensure it wasn't in use during the upgrade etc etc We've even done an 'in-place' upgrade of SQL Server, again planning is everything.

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Posted
Unless it is a DC, in which case the roll-back plan must be to delete it and build a new one. A snapshot restore of a DC is nothing but pain anguish and a potential forest rebuild

 

 

Also, as well as Exchange server, you should not in-place upgrade a server with Azure AD Connect installed. If you do AADC stops auto-updating.

 

You should check the upgrade plan for each service running (NPS, DHCP, Certificate Services etc.) and make sure 3rd party software is compatible with he target version.

 

Yup if a DC goes wrong then you'll not want to restore it.

 

I'd be getting rid of that Exchange server all together.

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Posted
You must back up your DCs so you have a viable Disaster recovery plan. Sometimes bad things happen. When you rebuild from bare-metal, having a fully operational and populated domain makes the rest of the restore much easier and lessens the disruption to the rest of the organisation.
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Posted
No-one would ask if you wipe and rebuild going from Win 10 1903 to 1908 cos MS have invested massively in the upgrade process, this is what you're benefitting from here with an in-place upgrade
Posted

Thanks everyone

 

Should have said that they are VM's running on Hyper-V and the Hosts also need upgrading so need to work out how I'm going to do them as well. I have two hosts so was just going to upgrade one (with no live VMs) and then migrate everything over so I can do the other. If I was to do this I would probably install a fresh copy of 2019 rather than an in place upgrade. Does that sound feasible?

Posted
When i upgraded my hyper v hosts i used the move VM function in hyper v to move the VMs on to the second host then upgraded the first host. When i was happy with the set up i moved the VMs to the first host then upgraded the second. Was a simple process :)
Posted
Thanks everyone

 

Should have said that they are VM's running on Hyper-V and the Hosts also need upgrading so need to work out how I'm going to do them as well. I have two hosts so was just going to upgrade one (with no live VMs) and then migrate everything over so I can do the other. If I was to do this I would probably install a fresh copy of 2019 rather than an in place upgrade. Does that sound feasible?

Im glad someone else has asked the same question. I have 2 Hyper-v hosts running 2012r2 connected to a SAN via iSCSI and they are now at a point where i cannot apply windows updates to them because they are so far behind.

 

Anyways, i was hoping i could do an inplace upgrade on them but someone told me it wouldn't work.

Posted
Also remember Server 2021 is now on VLSC and i believe you can do implace upgrades still from 2012R2 to 2021 - with some of the warnings above like exchange is a no no etc...
Posted
Also remember Server 2021 is now on VLSC and i believe you can do implace upgrades still from 2012R2 to 2021 - with some of the warnings above like exchange is a no no etc...

 

Server 2022 is available but changes how things like LAG LACP connections work so it's not as simple as moving to 2019 if you're using that.

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