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I didn't leave the job, but I had my resignation letter written over this since I would have had to maintain it:
My former boss had an absolute hard-on for "AI" and brought in this low-bid, fly-by-night "AI" software to automate all of our processes. I'm a fan of automation in general, but not this.
This "solution" was basically a glorified macro generator that would screen scrape data from our apps and key into our other apps. Not only it was built on the absolute shakiest platform imaginable, but the documentation from the vendor outright told you to setup remote desktop services in a way that was in violation of licensing in order for it to work. The stack it ran on made a Rube Goldberg machine look like sleek, fine engineering.
I repeatedly told him this was bad software, but he persisted to the point where we nearly went to production with it.
The worst part? The applications he was screen-scraping were all internally-developed. We had access to the backend, frontend, everything. Rather than writing proper processes, he threw that piece of garbage at it.
Luckily he retired before it went to production, and the new CTO shut it the fuck down.
So, I didn't quit my job over it, but I was looking and had my resignation letter written.