Outlook: With a send delay enabled, any email in outbox waiting to send that gets selected gets changed to a draft and will not send.

AngryViking32 46 Reputation points

I have seen this happen with users in different organisations in different outlook clients.
We can easily replicate the issue:

  1. Enable send delay in Outlook Rules
  2. Send an email
  3. Select the outbox folder
  4. You will see the email change from a waiting send to a draft

This happens even with preview and preview pane turned off.

Outlook Management
Outlook Management
Outlook: A family of Microsoft email and calendar products.Management: The act or process of organizing, handling, directing or controlling something.
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  1. ChristyZhang-MSFT 21,181 Reputation points Microsoft Vendor

    Hi @AngryViking32 ,

    Welcome to our forum!

    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…);
    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.

    In order to further confirm your problem, please provide the following information related to 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?

    If the response is helpful, please click "Accept Answer" and upvote it.
    Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

  2. Mattias Lindqvist 1 Reputation point

    Did you find any explanation to this? I am experiencing exactly the same issue. I have a delayed delivery of 1 minute for all outgoing messages and this has worked flawlessly for years, but lately I have started to experience the same issue as explained above. When I click Send the message often (but not always) goes to the Outbox but remains as Unsent, or turns into Unsent automatically within seconds. Very annoying...

    My rule is as follows:

    The outlook version is:


  3. Marco 1 Reputation point

    Same here. I've found that merely looking into the outbox folder to see what's going on prevents the emails there to be sent out. Terribly frustrating.

    My Outlook version is Microsoft® Outlook® for Microsoft 365 MSO (Version 2202 Build 16.0.14931.20118) 32-bit

  4. Patricia 0 Reputation points

    Hi! Was there a solution for this issue? I'm experiencing the same thing with 2 users
    Delay is 1 minute
    I tried to repair office, redo the rule, redid her Outlook profile

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