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
    2023-01-18T17:51:52+00:00

    Dear DominicWB

    Good day! Thank you for posting to Microsoft Community. We are happy to help you!

    According to my test on my outlook 365 client, delayed messages will be located in the Outbox folder before sending, and can be successfully sent and located in the sent folder at the set time. The specific operation steps are as follows:

    1. Create a delay rule(File>Manage rules &Alerts>New Rule…);
      123572-6.png
    2. Send an email;
    3. Select the Outbox folder/select the email in the Outbox folder, the email is still Outbox folder;
    4. When the set time is up, the mail is successfully sent and located in the sent folder.

    Could you please make sure that this feature is enable

    Image

    Also make sure that the Send/Receive options are this way ( the schedule an automatic send/Receive every… should be unchecked)

    Image

    Because my testing process didn't have problems, I need to gather more information to help you better, so I can narrow down the problem:

    • What's the version of your Outlook? (File > Office Account > About Outlook). Please make sure you have upgraded your Outlook to the latest version.
      How did you set that rule?
      Will the issue occur when setting delay for a single message(options>Delay Delivery) without using rules?
    • What's your account type?(business account/outlook.com/hotmail.com/pop account/imap account)
    • Please kindly try to use Outlook on the Web and let us know the result.

    Thanks in advance for your understanding! Your patience and cooperation will be highly appreciated. Hope you all the best!

    Sincerely,

    Kerry Chen | Microsoft Community Moderator

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  2. Anonymous
    2023-04-05T14:21:42+00:00

    I have this exact same issue. I have my rule set up the same way and have all of the same settings as described in the suggested troubleshooting.

    I am using Microsoft® Outlook® for Microsoft 365 MSO (Version 2208 Build 16.0.15601.20526) 32-bit

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  3. Anonymous
    2023-04-24T11:38:09+00:00

    I have the same issue - I have a 2 min delay set up. It seems that messages send correctly, but that viewing the outbox causes the process to stall, and it is then impossible to send the email. The only way to get the stuck messages to send is to forward them.

    This seems to be a software glitch. I would really like advice ASAP if there is a setting that can be altered to rectify the problem.

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  4. Anonymous
    2023-04-26T14:18:00+00:00

    Same issue for me - it's been doing this for a while but it used to be less frequent. It now seems to happen about 50% of the time - not fun realising the important email you sent a few hours ago never actually got sent.

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  5. Anonymous
    2023-05-30T16:24:41+00:00

    Same issue with 1 minute email delay.

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