this post was submitted on 04 May 2026
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I've worked at a company where the entire billing system ran on a Windows Server 2003 machine, running in a Vmware Workstation Player 15 VM on a Windows 8 PC.
The billing software wasn't actually billing software, it was a kind of build your own software toolkit heavily customized. Like, a sort of simple scripting engine. The actual program was no longer available and would only run on older versions of Windows even if it was. There was no installer available for it. If any part of this setup failed they would be unable to process invoices. The data format was totally proprietary with no way to export it to any other platform.
The whole setup was accessed by remote workers using an unprotected RDP connection. No VPN.