I don't have a chronological list, so this might not be my second free software program, but it's an early one.
My first foray into Debian-specific tools, dpkg-repack does one simple job and does it well. The second best part of doing dpkg-repack was just learning enough about the underpinnings of Debian's package manager to work out that it was possible to do. The best part has been the ensuing 9 years of seeing random mentions of it saving someone's time or data.
It's been pretty low maintenance ever since I wrote it, with the occasional tricky issue to resolve. I still use it as frequently as anyone else, which is not very often. Just another tool it's nice to have put in the general toolkit.
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