He should have asked how many letters in the word and then to name off each of those letters to the corresponding number, I would have liked to see the response to that.
If you see the clip of him speaking to it (he's using voice chat on his phone and recording with another phone), it counts the 3rd 'e' as the 3rd 'e' twice. It doesn't skip it, it just doesn't process two 'e's adjacent as separate.
I saw the same glitch previously when someone asked it to count the 'r's in "strawberry". It just doesn't properly process the repeat letter.