Exception to Outlook Rule is not working

Question

I have set a rule to delay all outgoing emails by 1 minute but have set an exception that if it is assigned to any Category, it should be sent out immediately. When I do not assign a Category, the mails are going out after the 1-minute delay. But when I assign it a Category, instead of being sent immediately, it gets stuck in Outbox! And if I edit it after that and remove the Category assignment, it doesn't help and is still stuck. I have tried deleting the rule and recreating it but it still doesn't work.

Answer 1

Hi @Prakash Grama ,

Welcome to our forum!

According to your description, sounds like that the Outlook Rule you set is reasonable, and the stuck issue should have nothing to do with your Outlook rules.
Can emails be sent out normally if you disable all your Outlook rules?
And how did you add categories to those emails you would like to send out? Maybe this similar thread could help: Can't send delayed email immediately in outlook.

As I know, there might be several common factors which would cause similar issues, for example large attachments, corrupted datafiles or profiles and others. Please follow the steps in this article: Fix messages that are stuck in the Outbox and see if it could help.

If the issue still continues, I'm afraid there might be something wrong with your Outlook datafiles or profiles, so please try creating and using a new Outlook profile via Control Panel > Mail > Show profile and see if this issue could be resolved.

By the way, firewall and anti-virus program may also influence this issue, please remember to check them.

Hope this can be helpful.

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Answer 2

Hi @JeffYang-MSFT , Yes, I am assigning categories the way you have said and my rule is also defined that way.

I tried 3 things: (a) created a new Category called "Send Immediately" (so that I don't use the color categories), set the rule to send immediately only when assigned to that category (b) changed the rule to send immediately if it is Yellow category and assigned a message to Yellow, (c) changed the rule to send it out if assigned to any category and set a category. In all cases, they get stuck. I can see the category in the Outbox and only the mail assigned with the category gets stuck.

I also tried another test where I set the exception category to Yellow and assigned a Blue category to see if it will go out after 1 min-delay (like all emails that are not assigned any category). And it got stuck!

Then I thought maybe my rule is blocking emails with any category and deleted the rule. Then I assigned a message with a category. And even that got stuck!! So the problem doesn't seem to be with the rule at all and instead is with a category being assigned to any email!

I have been restarting Outlook every time I changed the rule just to make sure it is applied but not rebooting.

I would appreciate it if you would test out sending an email with a category without any rules set and see if you can duplicate it. Any other thoughts?

Thanks for your help.

Answer 3

Hi @Prakash Grama ,

Thanks for your detailed reply.

Before going further, may I know what's the version of your Outlook? (File > Office Account > About Outlook). To avoid version-related issues, please make sure you have upgraded your Outlook to the latest version.
And what's the type of your account? POP, IMAP or Exchange?

I would appreciate it if you would test out sending an email with a category without any rules set and see if you can duplicate it.

I tried lots of tests in my Outlook 365 (Version 2008 Build 13127.21348) about, with or without rules, emails with category can all successfully been sent out normally, , as designed. Does this issue only happen to the specific email account on this specific Outlook client? In order to further confirm your issue, it is suggested for you to try the same tests for other personal email account and see if the issue has any difference.

By the way, personally I think repairing your Outlook program might be a necessary step about your issue.

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Answer 4

Hi @JeffYang-MSFT ,

My Outlook version is Microsoft Outlook for Microsoft 365 MSO (16.0.13801.20288) 64-bit. My Windows version is Windows 10 Enterprise 1909 OS Build 18363.1440 installed on 7/24/2020 on a HP Spectre Split 13x2 PC 13-m010dx running an Intel Core i7-8550U CPU @ 1.80 GHz 1.99 GHz and 16 GB RAM

I figured out that I am having this issue only on my desktop app and not online, where it works fine. On the desktop I tried all 4 combinations:

1. Send with category and with rule
2. Send without category with rule
3. Send with category after deleting the rule
4. Send without category after deleting the rule

The emails go out in case of #2 and #4 but get stuck in Outbox for #1 and #3. Hence I felt that the issue is not with the Rule but with the Category. I tried to Repair it but after a while it said something went wrong. I will run it again.

I asked my colleague to test it and it works fine for him with the Category from his desktop app. So it may be some corruption on my laptop? I have a spare laptop and will try it on that over the weekend.

Thanks,
Prakash

Answer 5

Hi @JeffYang-MSFT

I tried to Repair but it ran into an error. Later I realized that it had uninstalled Office 365 from my laptop!! I reinstalled it from online. Now the rule works fine. All emails by default are delayed by a minute except when assigned a Category where it is sent immediately. Thanks for your help!