Installing Cisco CallManager 4.1(3) on VMware in 2025

Getting Creative Again – and Reinstalling 2005 in 2025

It’s certainly been a while—and a lot has changed in my life. But I’ve been wanting to get back into more creative projects, especially the kind that mix creativity with something deeply technical. This one definitely checks both boxes.

Get ready to Collaborate like it's 2005!

Please check out my YouTube video.

Installing Cisco CallManager 4.1(3) on VMware in 2025

When I first had this idea, I figured it would be a quick weekend project—knock it out in a couple of days and move on. Many months later, I can finally call it a success.

The Classic Method (That No Longer Works)

Historically, you'd follow a guide like this one to install CallManager 4.x. It relied on:

  • Installing vanilla Windows 2000 Server
  • Modifying the registry to bypass hardware checks
  • Applying Cisco OS update files like win-OS-Upgrade-K9.2000-2-6sr4.exe

But in 2025? These Cisco OS update files have vanished from the internet. Despite hours of searching, I couldn’t find a single one.

The Backup Plan: Cisco IP Telephony Operating System

So what's Plan B? Install the Cisco IP Telephony Operating System—a customized Windows 2000 image that runs from the Windows Preinstallation Environment (WinPE). The WinPE files show Windows version 5.1, so it looks like Cisco used WinPE XP to deploy the Windows 2000 images. Fascinating. I wish I could find some older versions of the Cisco IP Telephony Operating System to see how it worked prior to this.

If you're brave (or reckless), and would like to follow along, you can try searching for "2000-4-1 (7825-H1).iso" on Google. I won’t link the sketchy FTP source I used—tread carefully.

VMware Doesn’t Like It

Naturally, you'd assume Windows 2000/XP = works on VMware (at least at a basic level). Nope.

The Cisco installer performs hardware checks and expects very specific platforms. VMware fails these checks, and the installer can’t find a compatible disk controller, no matter what:

  • IDE: ❌
  • SCSI w/ F6 drivers: ❌
  • Injected drivers into WinPE: ❌

No luck. Maybe I just don't understand how to properly get different drivers to work with WinPE.

Trying Windows 2003 Instead

A Windows 2003-based Cisco OS version had better driver support and—surprise—it ran perfectly on VMware. Unfortunately, CallManager 4.1(3) only supports Windows 2000, not 2003. So, still no luck.

Franken-Installer: Merging Win2K into Win2K3

At this point, I got creative. Since both versions were deploying an image under the hood, I thought—what if I inject the Windows 2000 image into the WinPE 2003 installer?

After plenty of trial and error (and some very late nights), I managed to:

  • Inject the W2K deployment image
  • Copy over post-install routines
  • Get a working Windows 2000 base install

Finally, I had a platform where CallManager 4.1(3) could theoretically run.

DC Directory Fails & Perl Enters the Chat

The CallManager installer seemed to go fine… until CD 2, when DC Directory failed to install. So I dug into the logs and found an error in reference to a Perl script: ConfigureSSL.pl.

But Cisco’s installer deletes these Perl scripts after each run. I used Process Explorer to find the installer args, copied the temp install files before they got deleted, and tried running DC Directory manually.

I then wrote some batch files to loop and back up the Perl scripts the moment they were created. Eventually, I captured everything I needed.

The SSL Problem (and the 20-Year Cert That Wouldn't Die)

I got the Perl environment working and found the script was failing in two places:

  1. Updating the OpenSSL config file
  2. Generating a 20-year self-signed certificate

On a hunch, I changed the expiration to 10 years. Suddenly—it worked!

Automating the Fix with AutoHotKey

To automate this during a real install, I used AutoHotKey to intercept the osltool.exe OpenSSL calls. I:

  • Monitored the filesystem for osltool.exe
  • Renamed the original binary
  • Planted my own AHK-compiled binary in its place
  • Rewrote the 20-year cert request to 10 years

With that, CallManager 4.1(3) installed successfully 🎉

But Why Was This Ever Needed?

This issue never happened back in the 2000s, so why now?

After more research, I discovered the culprit: the Year 2038 bug. The old version of OpenSSL bundled with CallManager can’t handle dates beyond Jan 19, 2038. I mistakenly assumed that this was a Linux problem and didn't impact Windows. Oops.

  • 2025 + 10 years = okay
  • 2025 + 20 years = no dice

I verified this by tweaking expiration lengths until failure occurred exactly at the 2038 limit.

The Much Simpler Fix

All of this work... and there’s an easier way:

Just set your system clock back to 2013.

That's it. Do a clean install, roll back the date, and CallManager installs with no hacks needed. Wish I had thought of that sooner.

Final Thoughts

I tried compiling newer versions of OpenSSL that still support Windows 2000 (like 0.9.8h), but they’re not Y2K38 compliant either. Maybe someone with more experience can cross-compile a modern OpenSSL for Win2K, but that’s beyond me.

For now, setting the clock back is the easiest, cleanest fix.

Thanks for coming along on this adventure. Next time, we'll try to install an old version of Unity. Or set up an old PoE switch and register some phones. Or something else that strikes my fancy.

Oh, and if you have any old versions of Cisco IP Telephony Operating Systems, OS Updates, or any other old Cisco software, please let me know! Throw it up on Internet Archive and drop me a note, or just send me a link.

Edit: I've uploaded the ISO to archive.org in case anyone else would like to experience a small portion of the pain for themselves: https://archive.org/details/hp-2003-1-3a-dvd-w-2-k-4.6

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