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Emails being Received sometimes unreliable.

I have multiple cases of my email being sent(receiving no errors back) and the receiver is not getting the mail. But since i have been made aware of the issue and am tracking it, both times it has came up again once we try to resend the receiver reports they have received it. I have been on help chat's where we update the mx records and test the email is working.

Any ideas where to look or how to troubleshoot it? Email is not one of my strengths. 

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I believe i have ruled out outlook, because i am using smtp and can see the emails being sent on the web inbox.