What hurts the most during your job hunt?

Automatic rejection is such a canned response.  It's always the same words, you can tell, after you've put in effort, that there was no effort made to even review your CV.  You just weren't aware of the algorithm that the ATS was using, so you couldn't give it what it wanted - even if you seemingly are a good fit for the job.  Seems a shame that the skill they're testing for is how to beat the ATS.

Actually all but automatic rejection is the stupidest thing.
Recently I applied for a new job at one of the great companies in Dubai. They told me I was lucky because their automatic rejection workflow wasn’t working properly when I applied and I should have been rejected because of the number of years I entered for one of the questions.
Now I passed the third interview round with them and waiting for the offer :)