Delay rule in Outlook causing emails to get permanently stuck in outbox

Anonymous
2023-01-18T15:42:26+00:00

I have a three minute delay rule set up in Outlook. Previously this has worked with no issues, however, now about 50% of my emails get stuck in my outbox when they send. After hitting send the email goes to the outbox with the 'editing' symbol (piece of paper with pencil) next to it rather than the 'send' arrow symbol. If, after three minutes, send/receive is pressed the email won't send. If the email is opened and send hit again it wont send. The only way to send the email is to copy the text into a new email and send that. If I turn the rule off the issue goes away.

My internal IT department has been unable to help, they have run the repair function, created a new profile and reduced the downloaded emails, none of which helped.

Thanks in advance for contributions.

Outlook | Windows | Classic Outlook for Windows | For home

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  1. Anonymous
    2024-07-25T09:40:30+00:00

    Same here, I've been using this feature for years and since a couple of months this feature is broken. I confirm that checking the outbox during the delay time seems to be the cause of the problem. Dragging and dropping to Drafts folder and then hitting send works every time but this workaround is very tedious and not ideal. Please fix this. This is a crucial feature for many!

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  2. Anonymous
    2024-05-16T14:13:44+00:00

    same!!!! I call someone 2 hours later to ask about an email that never went anywhere! I am still not seeing a fix on this and I have all the setting the same as what they suggested. So frustrating.

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  3. Anonymous
    2024-05-14T21:18:02+00:00

    I've been having the same problem for a couples months. DuckDodge****1 suggestion was very helpful but it's crazy that you should have to do this.

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  4. Anonymous
    2024-04-29T17:46:17+00:00

    Oh, I just posted this discovery too. Your solution is even better. But moving to Sent folder (and then finding and resending) also worked.

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  5. Anonymous
    2024-04-29T17:43:42+00:00

    Same problem for me. I was not able to disable the Adobe Cloud add-in (though I do have it, so perhaps that is my problem).

    For what it is worth, temporary fix for me: Drag and drop the stuck message from the Outbox to my Sent Items. Go to Sent Items, reopen e-mail. Now hit SEND again. This time, it reactivated and sent out. For me, sending again from the Outbox without moving it did not change the stuck status of the message.

    The problem occurs when I send an e-mail. Remember or see something I want to change during the delay time period (which is literally why I have the rule), and reopen. And hit send again. Without the above steps, the resend does not rearm the e-mail, and it stays stuck.

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