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

Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.

0 comments

47 answers

Sort by: Most helpful
Most helpful Newest Oldest
  1. 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.

    Was this answer helpful?

    4 people found this answer helpful.
    0 comments
  2. Anonymous
    2023-10-18T00:20:44+00:00

    A quick fix I found is to (1) go to your outbox, (2) right click the email that is stuck, (3) move the email to drafts, (4) then find the draft email, and (5) hit send again. May not be a long term solution, and very tedious (would much rather just have the rule work), but that at least fixes the immediate problem.

    Was this answer helpful?

    4 people found this answer helpful.
    0 comments
  3. Anonymous
    2024-03-30T18:16:49+00:00

    Dear Community Members,

    I am very glad I found this thread. I did experience the issue for a while.

    I do not have the add-in Adobe Document Cloud for Microsoft Outlook.

    The resolution for me was to disable two barely used add-ins:

    • Microsoft IME Outlook アドイン
    • Outlook Social Connector 2016

    Outlook seemed to hang for a few seconds. I waited then I tested my defer rule and it worked.

    It is worth noting enabling again the two add-ins above did not affect the resolution. The defer rule continued to work even with the two add-ins enabled back again.

    Was this answer helpful?

    3 people found this answer helpful.
    0 comments
  4. 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

    Was this answer helpful?

    3 people found this answer helpful.
    0 comments
  5. 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)

    Was this answer helpful?

    2 people found this answer helpful.
    0 comments