That's a programmer's understanding of linguistics. You're highlighting descriptive features which are approximations of averages of how we speak English under

That's a programmer's understanding of linguistics. You're highlighting descriptive features which are approximations of averages of how we speak English under perfect recording conditions in a specific dialect. There is way more variance and alternation to how people pronounce words than what you're suggesting. How those sounds get interpreted by STT engines is likewise subject to this same variance. IPA isn't code. We don't perfectly reproduce sounds when we're speaking and certainly not to the letter of an approximated IPA transcription. You didn't correctly transcribe Trump, btw. It's /ˈtɹəmp/ for American English. But it does exemplify my point: there are absolutely people who pronounce Trump with an unrounded vowel and STT engines have to account for this (and they get it wrong for people who are further from the average, outliers). There are a lot of people who use a triphthong when saying racist as in [ɹɘeɪ]. With a short recording window, it's totally plausible to have these sounds be misinterpreted.