What version of CCM would've been on WinNT? This is likely a 3x or earlier system. For example, 3.0(1) ran on Windows NT.
Would it even be possible to migrate to a more current version? If the system is 3x or earlier as I suspect, you would be looking at EOL/EOS hardware and software. There would be no direct migration path to a current version of CUCM. Your best bet (in all honesty) would be a new hardware install. You could try and use BAT to retain as much phone and user data as possible but the upgrade path would likely be convoluted and very limited.
What licensing changes has there been since the NT days? Licensing has moved from DLU only to CUWL. So, user-based licensing with feature bundles vs. device/software-based. In addition, many environments like this do not have a current support contract so they cannot order upgrades and would be required to go about migrating as if they are installing a new system.
Any caveats I should worry about? Just make sure you understand the end user requirements on the old system and explain the many options available today. You'll want to get familiar with CUWL licensing and scope out what new features would benefit the customer.
Wow, NT 4.0 huh. Well, the only versions of Call Manager that I have seen run on Windows NT 4.0 were when the Selsius solution was first acquired. I think the version 2.4 or something along those lines. I recall deployed 3.0(3) and I believe it ran on Windows 2000 at that time. So, your version pre-dates 3.0(3) at least (I just looked at the BoM from that project, 3.0(2) was what was ordered, so maybe 3.0(2) is Windows 2000 as well).
So, the 3.0 train is EoL and I don't think that there would be a license upgrade option available. There definitely is no migration path from 2.x/3.0 to any of the modern CUCM releases. If they are running voicemail from this "era", then it is either a legacy system (like Octel). If it is an IP system, then it is either Active Voice (the technology Cisco acquired circa 2000/2001 to make Unity) or it is the first "Unity". OR, it could be uOne Enterprise. Which would be absolutely hilarious. Sorry, but it would be. Voice gateways from this time frame will be 2600 or 3600 (maybe a MC3810 if there is a legacy switch floating around). It is possible the phones are 7940/7960. They would have been brand spankin' new at that time. It is also just as likely the old white selsius stations are floating around (the ones with no MWI light, quality). None of that will be re-usable. Highly unlikely any of it can be upgraded. But, the Cisco AM may be willing to work out a deal. Depends on the customer and depends on the AM.
From a technical stand point, there will be no direct migration path. There may be a multi-stage path, but it will not be worth the effort. You are better off treating this as if it were a legacy system (which it is) that you are migrating from. The customer may want to push to keep something (like phones). Ideally, you get them away from that idea. You'll have to play that by ear.
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