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drakesdoom ago

Not those two words, but some mobile gesture keyboards can put out some uncommon misspellings.

Vaati ago

as someone with one of those swipe keyboards, I don't think when and win is a mistake you would see from that. When requires you move right, then left, then right again. Win is a swipe right and then down. You would be more likely to get run when trying to write win than you would be when.

The big error I would look out for is negative contractions. My personal experience with text to speech software (and the reason I no longer use it) is that it very frequently mixed up things like can and can't.

edit: points for reading comprehension please? I totally missed the 1/4 of your post where you say that those two words couldn't be mixed up. In any case, the fact that they don't make sense as that type of error means it is more likely a text to speech mistake.