The Transcriber for Linux works like a charm, but as you could tell from my last blog post the Windows install suffered from a bunch of problems. I built the Podcast Idiot Transcriber through conversation with Claude.ai. I describe what I want, Claude builds it, I test the result on an actual machine, a Dell XPS 13 running Windows 11, and I report back to Claude exactly what happened. Getting the installer to work on Windows took a lot longer than I figured it would, since Windows is so widely used that I expected Claude to have less trouble building for it than for Linux.
The installer kept failing
The installer checks that the right pieces are on the computer, installs whatever’s missing, and confirms everything works. I wanted a simple file that a user could double click to get it running. In the beginning there were some oddball symbols that showed up as garbage characters in the installer window. That was a simple fix. Then a harder problem showed up: the installer would sometimes tell me it succeeded even when a step had failed. I found out later when trying to use the app and it wouldn’t transcribe the mp3 I handed the program. Claude figured out it needed a log file I could give it so it could determine exactly where the software stopped and what was missing.
ffmpeg turned into its own headache
The app also needs a separate piece of software called ffmpeg to handle audio. The installer tried to fetch it automatically using a tool built into Windows. On my machine this worked sometimes and failed other times, with no clear pattern I could see from my end. I’d run it, tell Claude what happened, run it again, rinse and repeat. Eventually Claude found other people online had hit the same unreliable behavior with that specific tool, which had nothing to do with anything in our script. So instead of relying on it, Claude changed the installer to download ffmpeg directly and place it exactly where the app expects to find it. That cleared up a whole category of random failures on my laptop.
The mystery failure
The toughest bug was a silent crash partway through installing on a freshly wiped version of my laptop. The installer window would just close, no error message, nothing. I went through a long list of things to rule out on my end at Claude’s direction: turning off antivirus, moving the folder out of Dropbox, checking disk space and memory, digging through Windows’ own crash logs. There was a ton of back and forth between me and Claude. None of it explained the crash.
I decided it might be better to start from scratch
After enough rounds of this, the pattern became clear. The same failure kept resurfacing in different forms no matter what I changed on my end. The script itself was a Windows batch file, and Claude explained that batch files are bad at catching their own errors. A step can fail and the script has no reliable built-in way to notice, unless every single check is written by hand, which is easy to get wrong.
So I suggested to Claude to start fresh from the beginning. It already knew what I wanted and knew the Linux version worked like a charm. It’s funny to watch the AI have an epiphany. Claude rewrote the entire installer using PowerShell instead. PowerShell catches errors properly on its own. I ran that new version on my laptop, and it’s what finally worked. Once it could actually detect when something went wrong, the remaining problems became things I could see and describe. That gave Claude a clear path to finishing the app.
Last touch: a blurry icon
With the installer working, the only thing left was cosmetic. The app’s icon looked blurry on my desktop and in the Start Menu. I mentioned it to Claude, who tracked it down to the icon file only containing one very small image, which meant Windows had to stretch it to fill a much bigger space on screen. I created a new multi-resolution .ico file and handed that over to Claude so it could include it in the installer.
What I learned
I can’t assume Claude just builds everything correctly. I should already know this given how much back and forth it took to get the Linux version working. For some reason, I figured that if the Linux version worked then it would make the appropriate changes to the Windows version and that would work automatically. It’s a good thing I still have a Windows machine to test this tool out. The next step is to try this on a Mac.
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