My Scheduled Emails aren't appearing in the 'Sent' folder

On Sunday, I scheduled 2 important emails to send at 8am on Monday Morning. It's now Wednesday and both emails are in the 'Send Later' folder and a note above says 'these emails will be sent on Monday 22nd April 8am' even though that is now 2 days in the past.

Neither email is in my 'Sent Items' folder.

I cancelled 'send later' for both emails but now, whilst still listed in the 'Send Later' folder, they are completely empty - no content, no attachments.

Got to say this is something of a mess. Any ideas?

Having do a similar Test and can not duplicate the issue

The caveat - 3rd image show Sent After does have 1 message to be Sent

As mentioned earlier

100% Close Mail, pause 5 seconds, reopen and Send Later count is Zero Count

Apple is not here. This is a user forum.

Use the feedback page to report the issue.

https://www.apple.com/feedback

VWeisman wrote:

How can I check that a send later scheduled mail has actually been sent?

I have started using the send later feature on my apple mails. I schedule a mail to be sent on a later date. I can see the mail in the "send later" folder i.e. all looks okay.

I ensure my macbook is up and running and the internet is available at the time the mail should be sent.

(Although I expect anyway that the mail should still be sent as soon as I boot up my macbook or make internet available should that be the case). In this case the internet is available and the macbook is running at the schedule send time.

When I check after the scheduled date and time I can see that the scheduled mail is no longer in the "send later" folder. So it appears as if it has been sent. However I cannot see the mail in the "sent" folder. Why? Is there somewhere else I should be looking? Is the mail really sent? I also BCC myself and i did not receive the email.

These are important messages so i won't be using this option again until i can be sure the messages are actually sent.

Please help. Thanks.

100% Shutdown the Mail Application

Pause maybe 10 seconds

Re-Open Mail and check again

Have experienced this from time to time and doing this Seems to nudge 🤞 the Mail to re-index

This is a feature that I have not had a reason to use. I did a short test, by creating a message from one of my accounts to myself in a different account. I set it to send a few minutes later, it appeared in the Send Later box; I received it a few minutes after the scheduled time, but the message still shows in the Send Later, and NOT in All Sent...

Two different configured computers from two different contributors does make it a Bug per se

3 different Computers here, two of which previously on Ventura and now Sonoma 14.4.1

The Third ( M3 ) started with Sonoma 14.3 and now also on Sonoma 14.4.1

The suggested method " Just Works "

Start now and open an Apple Support Ticket as they are PAID  Apple Employees to deal will these types of issues . 

Interesting ?

I have reported via the Feedback Assistant built into MacOS