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Mac mail outgoing mail disappears

My outgoing emails on my PowerBook seem to be send (they make the swoosh sound) but they disappear, never get to their destination and don't appear in Sent box. Emails sent from the same account on my phone work fine. Mail does not quit when I click "quit". I have to force quit. Incoming mail works fine.

MacBook Pro 15″, OS X 10.10

Posted on May 18, 2023 6:37 PM

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Question marked as Top-ranking reply

Posted on May 28, 2023 3:27 PM

ninaeisenman wrote:

My outgoing emails on my PowerBook seem to be send (they make the swoosh sound) but they disappear, never get to their destination and don't appear in Sent box. Emails sent from the same account on my phone work fine. Mail does not quit when I click "quit". I have to force quit. Incoming mail works fine.


After you Force Quit your Mail, when you relaunch it hold the Shift key down. Quit Mail as normal(?) See if this resolves any issues.



I would turn off all the bells and whistle and compare your results:


Turn off undo send delay option:




Open mail app select Mail>Settings>Privacy disable:

“Protect Mail Activity”

“Hide IP address”

“Block all remote content”


reboot if necessary.


Also “Mail Privacy Protection” if no resolve, Mail>Settings>Privacy> uncheck

ref: —Mail Privacy Protection on Mac - Apple Support

Use Mail Privacy Protection on Mac - Apple Support



—if you are using Hide My email—try disabling this feature ...

Set up and use Hide My Email in iCloud+ on all your devices - Apple Support


—if you are using iCloud Private Relay on Mac - Apple Support try disabling this feature ...

Use iCloud Private Relay on Mac - Apple Support





ref: Mail User Guide for Mac


6 replies
Question marked as Top-ranking reply

May 28, 2023 3:27 PM in response to ninaeisenman

ninaeisenman wrote:

My outgoing emails on my PowerBook seem to be send (they make the swoosh sound) but they disappear, never get to their destination and don't appear in Sent box. Emails sent from the same account on my phone work fine. Mail does not quit when I click "quit". I have to force quit. Incoming mail works fine.


After you Force Quit your Mail, when you relaunch it hold the Shift key down. Quit Mail as normal(?) See if this resolves any issues.



I would turn off all the bells and whistle and compare your results:


Turn off undo send delay option:




Open mail app select Mail>Settings>Privacy disable:

“Protect Mail Activity”

“Hide IP address”

“Block all remote content”


reboot if necessary.


Also “Mail Privacy Protection” if no resolve, Mail>Settings>Privacy> uncheck

ref: —Mail Privacy Protection on Mac - Apple Support

Use Mail Privacy Protection on Mac - Apple Support



—if you are using Hide My email—try disabling this feature ...

Set up and use Hide My Email in iCloud+ on all your devices - Apple Support


—if you are using iCloud Private Relay on Mac - Apple Support try disabling this feature ...

Use iCloud Private Relay on Mac - Apple Support





ref: Mail User Guide for Mac


Jul 4, 2023 6:26 AM in response to Robert Kalk

Robert Kalk wrote:

The disappearance of outgoing mail is a serious problem that has remained unresolved for a year. The business critical mail app has been neglected for too long. There is no indication that an email has failed to send unless one gets a complaint from the person expecting it or the sender is in the habit of checking the Sent folder every time.

Why would Apple or any of its customers be so casual about such an obvious defect in the mail client? Why would the user be expected to do all the work-a-rounds described in this thread?




I do not use any of the bells & whistles that have been added,


never had the issue you describe before or after they where introduced.



You can submit your Apple Feedback here:  hhttp://www.apple.com/feedback


Contact the corporate office   Contact - How to Contact Us - Apple




Jul 4, 2023 2:22 AM in response to leroydouglas

The disappearance of outgoing mail is a serious problem that has remained unresolved for a year. The business critical mail app has been neglected for too long. There is no indication that an email has failed to send unless one gets a complaint from the person expecting it or the sender is in the habit of checking the Sent folder every time.


Why would Apple or any of its customers be so casual about such an obvious defect in the mail client? Why would the user be expected to do all the work-a-rounds described in this thread?

Sep 2, 2023 1:46 PM in response to leroydouglas

I am currently experiencing the same problem only on my desktop with Ventura. The laptop with Big sur and all ios devices work. Settting are the same across all of them. I'm going to work with apple to reinstall the op system and see if that helps. For now as a workaround I'm using a different email app to anwers my emails which works fine, on the same computer, with the same settings. Something related to mac mail on Ventura is the problem child, at least among all my devices.

Sep 20, 2023 2:06 AM in response to angelann

Exactly the same on my 15’ Macbook Pro. Creating a new mail does not work - seems to send with a swoosh ond nothing more.


Forwarding and replying work !!!


upgrade to 13.5.2 caused this … all was fine before.


turning off « undo send option » causes Mail to crash immediately.


Let’s hope for better days oder Sonoma !


or a fix from apple.

Mac mail outgoing mail disappears

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