Mail: The "Send later" option does not work correctly.

Are you able to resolve. Am having same issue

I tried it today and it did not work. I had two emails scheduled for 12.30pm and when I checked, both were still in the Send Later box. I did not try the solution offered by robfrankel as I only came across this topic now when searching for a solution. If it takes a reboot, deletion, recreation process to work, then it is a feature I will avoid using. I am trying to use Apple Mail in preference to Outlook.

I just started using the send later feature.

The first send later mail I sent did not go when it was supposed to. The second one did. New send later messages did not appear in the newly created send later folder under favorites. The feature started operating once I forced Mail to display the send later folder under favorites using the tip above. Unclear if the favorites send later folder must be present for send later to work at all, or if my first (and perhaps all first?) uses of send later just don't work.

Details:

I bcc all my emails to the sending address so that I know they sent successfully when I get them back (primarily for mobile with spotty connections) . My first message definitely did not go at the designated time. I opened it and sure enough it said "will be sent today at 9:02 AM" only to be stubbornly sitting there at 9:02:40 when I first opened it. I switched it to 9:04 and it went out. I know it did not duplicate send because I only received the BCC at 9:04.

Meanwhile I created another send later message as a test. The flag next to the send later item under favorites shows a "1" BUT, that message is not visible as an item in there.

When I close OSX Mail and reopen, then I can see them in there, and now a new one I just created DOES appear. glitchy.

Another test of the feature with a send later worked without a hitch, both showing up in the send later folder and sending when it was supposed to.

My conclusion is when the send later folder is first added to favorites, the feature does not work properly until mail is closed and reopened.

Okay, so the first thing you have to accept is that Apple Mail is a lot slower than it should be. Unlike the old, wonderful Eudora app, you can wait minutes for messages to download, sort or get sent out. So understand that everything happens a lot slower with Apple Mail.

However, I did get the Send Later to work:

I am currently on Sonoma 14.1. I did NOT rebuild anything. I simply restarted the MacBook Pro and importantly, deleted the old "Send Later" messages and re-scheduled them.

Don't expect any kind of alert that Apple Mail has actually sent the message. About the only indication you'll get is that the message in the Send Later box is gone.

Now, here's the typically empty-headed Apple feature: While the mail may have been sent at the time you designated, the app -- being slow -- may not update that Send Later box for hours and hours.

Best thing is to test it out, literally, over the course of a couple of days. Note when the recipient actually received the message and when the app updated to show it sent.

HTH

There is no rebuild mailbox option. Closest thing is synchronize.

Hi Frisco_Bay,

We understand you're having some trouble with Mail behavior and we want to help.

If you haven't already, try rebuilding the mailbox:

Rebuild mailboxes in Mail on Mac

Sync your Mail again and let us know if everything moves to the correct place.

Test sending an email to yourself if necessary.

Thanks for using the Apple Support Communities.

Hi Frisco_Bay,

We appreciate you reaching back out and letting us know that rebuilding the mailbox did not resolve the emails getting moved from Send Later to Sent.

What we recommend is reaching out to Apple Support so they can look into this with you further. They can be contacted by going to Get Support.

Take care!

Mine doesn't even send them at all, tried emailing myself first