Bot emails not sending

Hello, two weeks ago and now today, I have had an issue where the same bot is not sending an email, even though the monitoring shows as successful. I have had 4 other emails between now and then that did send through the same bot. I'm not really sure what's going on or what I can do anything to correct it. 

Any help is appreciated. Thanks.

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Hello there,

Did you check that...

1- Was the "To" email address correct?
2- Did the recipient check their spam folder?
3- Does it happen with the same email or it happens randomly?
4- Does the monitoring logs for the ones that "didn't send" the emails look the same as the ones that did?

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