App Migration to New Server

[MadManMoe]

Hello fellow admins,

 

Got a whopper of a task on my hand. Our company wants to migrate its 100s of windows 2012 servers to 2019/2022 servers.

 

Part of the problem is user apprehension of migrating their software to the new servers.

 

We already have multiple paths for user migration, but we're also looking into 3rd part apps which can handle server-to-server application migration.

 

Now, I'm still very new to app Migration, so let me state what I mean by app Migration:

1. All (or select apps) in the original server are "copied" over to the new server (preferably via network as all our servers are VMs)
2. By "copied" I mean fully installed over to the new server and fully functional
3. All necessary configurations are properly set up so user can use their application.

Basically, a magic wand that "poof" app works in server A now works the same way in server B.

 

I do have suspicions that some things won't work so well and would need actual work/configuration. These are just some off the top of my head:

• Apps which use host machine name as part of it's config will break due to new machine's name
• Licenses which deal with Machine GUID, MAC, or other hardware values will fail
• Some deep, dark, mysterious registry entry doesn't get migrated correctly. Leading app to fail
• Etc.

So, I'm not naive enough to think such magic wand exists, but I do need suggestions.

 

So, the question is: anyone out there have either used or can recommend a third party app that can perform this task? I have one in mind called Todo Advanced by easeus that sort of ticks these boxes, but any other suggestions are appreciated.

 

Thanks in advance.

[Electronics Wizardy]

Id just try to do a inplace upgrade from 2012 to 2022. Make a snapshot first, but it should work most of the time, and be the most seamless way to move to a newer os.

 

Otherwise can you get support from the app vendors, that seems like the best option here. If you can't do that, try using the installer if you have it, or copy the installed program files. You can also monitor a program to see what files and registery keys it's reading and copy those to the new system.

[MadManMoe]

56 minutes ago, Electronics Wizardy said:

Id just try to do a inplace upgrade from 2012 to 2022. Make a snapshot first, but it should work most of the time, and be the most seamless way to move to a newer os.

 

Otherwise can you get support from the app vendors, that seems like the best option here. If you can't do that, try using the installer if you have it, or copy the installed program files. You can also monitor a program to see what files and registery keys it's reading and copy those to the new system.

Hi, thanks for your input. So:

1. Our company deals with...a LOT of different vendors. I mean...A WHOLE LOT. That's the primary reason why we can't realistically communicate with each and every single vendor to develop this migration plan. Our team is little, and the users are many
2. Our more senior engineers have expressed their apprehension with an inplace upgrade as you suggested. Especially going from 2012(r2) to 2019 or 2022. I believe they faced some problems in the past with this method as well. It may be one of our "last resort" effort, but at this point I'm looking into 3rd party apps that may have a more robust option
3. one of our other "last resort" ideas is to just blatantly force the users to suck it up and manually reinstall their applications; however, this is a big company and many of the older (more complicated) apps that were initially installed/managed by someone has left the company. So, this is something we're trying to avoid as well.

Note: When speaking of apps, I'm not necessarily talking about regular commercial apps like Adobe products, office suites, or things of that nature. Many apps are either custom or have a very niche market that they are used in. 

 

Still, much appreciate your input and giving me a chance to add extra context to my challenge.

[wseaton]

Do one app at a time.

 

Migration vendors never tell you the pitfalls. It never goes smooth.

 

Do one app at a time.

[Sprawlie]

1: UAT ! Do not do anything in production until you have tested the upgrade in UAT first! 

 

2. This is an extensive project in any regards. Not a press a few buttons and voila, upgrade. Now, yes, from a technical side it MAY be that easy. But corporate projects need checks, balances and oversight to ensure that all thresholds set in the project goals are met, including any risk and what you're doing to mitigate any.

 

3. Snapshot, snapshot,snapshot. If it's in production. Backup, snapshot, backup. two copies. whatever. Don't fuck around if it's mission critical but ensure you have a back out plan in case it goes wrong. That could mean restoring a snapshot, or restoring from backup. But have the plan ready, and have something measurable that would kick off the execution of the back out plan.

 

4. User Apprehension is understandable, but cannot be a barrier to progress. I can attest to this from experience that constantly having to cave upgrades or innovation because of user sentiment, and you will never ever get anything done. Catching up from that far behind is signfiicantly harder, more expensive, and will be that much more oppositional. Get management buy in, With the plan above you'll be able to convince them that you're ready and know what you're doing. And if Management is in, The rest of the employees will fall in line or usually be shut up. 

 

5. @sweaton posters are also completely correct. One app at a time, Vendors are not your friends and likely will not share enough to make the transitions perfectly smooth. Be prepared to either have to pay for support, or rely on your own skills.

 

6. Checklist the exact steps you are going to do in production before you ever touch it. "LIVE" day should be following your own tested checklist of events without the need to think. if you planned and tested right. "LIVE" should be a sleep walk.

 

7. Have a second person involved with live who is fully aware of the checklist and can swap in place should you become unavaialble, or even just to ensure that what you're doing with hands on keyboard is accurate and you're not dozing off accidentally typing rm -rf in the wrong folder 

 

8. In place upgrade is your best bet, but if you hvae third party software that doesn't like it, you need to get that software installed from scratch. Migrating software (especially windows software, that uses proprietary code or engines) is ridiculously difficult and may have massive unforeseen repercussions. The only safe way is a proper, Full re-install from the vendor. Unless supported, you simply don't know what sort of behaviour you may encounter if proprietary software is not installed to the vendor specifications (I Know this as a former Vendor of proprietary software, AND sysadmin of proprietary software)