Outgoing emails from my Mac come back to me three days later addressed to me. Recipient never receives.

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Level 1

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Outgoing emails from my Mac come back to me three days later addressed to me. Recipient never receives.

Sporadic problem with apple email account. Happens about twice a week. Emails not being received by the recipient. Sending from Mac Pro desktop. The emails I am sending show up in my "sent" folder so I have no indication there is a problem but then three days or so later I receive the email back, addressed to myself, as if I originally sent it that way (to myself). I then ask the intended recipient if they ever received it and the answer is always "no". Using OS is Sonoma 14.5 Help!

Mac Pro (2019)

Posted on Jul 14, 2024 1:16 PM

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Answer 1

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Camelot

Level 9

59,127 points

Jul 14, 2024 1:48 PM in response to Denchamber

The message is bouncing - what you're seeing is the failure message from the mail server saying it's repeatedly tried to send the message, but it hasn't gone through, so it's sending it back to you. 3 days is the typical timeout for that.

you need to first check you're sending it to the right address. Then check the actual message you're getting - it will typically give you some hint as to where the failure is - i.e. whether it can't find the remote mail server, or if connections to that server were failing, or if the remote server rejected the message (although the last case would generally fail sooner).

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Answer 2

Denchamber Author

Level 1

14 points

Jul 14, 2024 2:11 PM in response to Camelot

Thank you Camelot. The address is absolutely correct in every case so far, and the message I get back tells me nothing about why it failed. See below as an example of what I get back three or four days later. I'm attaching a screen shot of what came back to me three days after sending.

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Answer 3

Camelot

Level 9

59,127 points

Jul 14, 2024 2:36 PM in response to Denchamber

Oh, this isn't a bounce message, it's a follow up (as you can see from the 'Follow up' button in the top corner).

Mail checked the message content and assumed you'd expect a reply. If you don't get a reply it flags the message for follow-up.

You can use Mail Settings to turn this feature on or off.

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Answer 4

Denchamber Author

Level 1

14 points

Jul 14, 2024 3:13 PM in response to Camelot

Thank you Camelot. This has never happened in the past - two emails a week (approximately) that are not received. It started a few months ago and I am certain I haven't changed any settings in mail. I'm thankful for the feature so I'm not about to turn it off. Two questions still remain, at least in my mind. Can I count on this feature to alert me whenever I send an email that is not received? Perhaps I can routinely include some wording in my emails that will trigger the feature, since you are saying that with the feature turned on, mail checks the message content to see if I am expecting a reply. And is there anything you can think of that is causing apple mail to fail to deliver the email in the first place? Thanks, Dennis

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Outgoing emails from my Mac come back to me three days later addressed to me. Recipient never receives.

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