Outlook:Send delay rule has a nasty bug. Changes all unsend emails in outbox to draft status

Question

Using the latest version of MS Outlook. ver 2102, build 13801.21050
MS365 Apps for Enterprise, subscription product

Nasty bug when using Send delay rule. I have been using this rule for years and this problem has cropped up in some update. Someone reported this in August but do not see any updates on it - (https://learn.microsoft.com/en-us/answers/questions/514647/outlook-with-a-send-delay-enabled-any-email-in-out.html) - @ChristyZhang-MSFT

Steps to reproduce.

1. Create a send delay rule. It is described in the above link by MS support person.
2. Send msg #1.
3. Send msg #2 before msg #1 has been send, waiting for x minute delay in outbox
4. The moment you hit send msg #2, msg #1 immediately converts to draft status.

Happens every single time and very easy to reproduce. Thanks

Answer 1

Hi @Lua ,

Welcome to post in Microsoft Q&A!

I searched around about the issue you described, but so far haven't seen other similar reports except for the thread you shared earlier. As there's no further feedback from the original poster in that thread, I tried testing on my side but failed to reproduce the issue.

Firstly, I tried testing in my Outlook for Microsoft 365 Version 2110, Build 14527.20234 (Current Channel), the delay delivery rule worked just fine.

Then noticed you are using "MS Outlook. ver 2102, build 13801.21050", so I tried building up a lab with the same build of Outlook as yours.

But still failed to reproduce the issue. The moment I hit the Send button for msg #2, the message in Outbox didn't convert to "draft" status, and after waiting for the specified time, both messages can be sent out and received as expected:

So according to the test results, I am assuming that there could be some other factors involved at your end that result in the issue. May I know if you happen to have any third-party add-ins enabled in your Outlook client? If this is the case, in order to elinimate whether the issue is related to any add-ins, I'd suggest trying to launch Outlook in safe mode(Press Win+R, type "Outlook /safe", note there's a space before"/", press Enter.), then test again and see if the delay delivery rule can work as expected.

Below is a thread which discusses about the delayed message turned into draft for reference:
Why does Outlook 2013 not send my email?
Please Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.

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Answer 2

Thanks @Yuki Sun-MSFT . Your response was spot on. It is not an outlook bug. McAfee DLP outlook plugin is forcing this behavior.
Your suggestion of using safe mode helped me debug this issue. I used "Outlook /safe3" to figure this out.