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
    2023-06-12T14:09:05+00:00

    I too have the same issue and have checked the settings as you suggest. Mine all match, except that per company IT setting my option for "send immediately when connected" is checked but greyed out so I can't remove it if I wanted to "cycle" the option as sometimes is suggested for seemingly random problems.

    I also have found that opening and resending the emails does not work, they perpetually hang in the outbox.

    I have only been able to replicate this problem when viewing the contents of the outbox. If I wait for my set delay time (1min), then I have no issues. If I view the outbox and try to watch it fly away then does not work.

    If I am currently viewing the outbox when I select send, I see the paper airplane icon, and the email will send. If I changed to the outbox when the email is already in the outbox then I see the editing icon, and it perpetually hangs there.

    I have also had success when moving a hung email to the drafts folder then resending. I had two viewing windows open one in drafts and one in outbox. I moved the email to the drafts folder, opened like editing and then resent. It curiously delivered immediately.

    It is like the cat in the box paradox.

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  2. Anonymous
    2023-06-29T01:11:15+00:00

    I have precisely the same problem which has started occurring in only the last 3 months (the rule has been working and in place for over 3+ years without any problems whatsoever).

    Would be good if Microsoft actually addressed issues and came back with a timeline for a fix

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  3. Anonymous
    2023-06-29T01:15:39+00:00

    Here is the rule I have setup for a deferred delivery by 2 mins - it's core functionality within Rules.

    I have an exception if there are any emails being sent to my personal email address or meeting rooms (which explains the grey box)

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  4. Anonymous
    2023-07-03T15:18:50+00:00

    Agreed- Same issue here. After last Microsoft upgrade, the delay rule stopped working if the email is edited. That's the entire point of the email delay rule! The email remains Un-italicized and stuck in the outbox. FIX THIS MICROSOFT!

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  5. Anonymous
    2023-07-03T15:43:35+00:00

    The email delay rule is not able to be configured on WebMail- FYI. Unable to set that rule up. Issue is the same for me. Current Outlook O365; and email rule stopped working after upgrade pushed by company on or around June 25th.

    Microsoft® Outlook® for Microsoft 365 MSO (Version 2304 Build 16.0.16327.20324) 64-bit

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