Outlook rule not working when run on demand

Question

Hi All,

I have an Outlook rule that picks up a specific domain and then adds a category to it.

Working: when an email from the domain arrives, it categorises it properly
Not Working: when I run the rule on demand with "Run Rules Now..."

The rule is:

• Apply this rule after the message arrives
• with @keyman .com in the sender's address
• assign it to the Internal category

Other rules I have run on demand absolutely fine (including this at the start: Apply this rule after the message arrives), but this one doesn't.

Attempts to rectify:

• Recreated the rule
• Tried different versions of the domain: "domain.com", "domain"
• Tried with @keyman .com in the message header - this works on demand but it also flags incorrect emails
• Tried a different category
• Tried OWA
• Restarted Outlook
• Restarted computer
• Assigned and unassigned category to email manually
• Ensured the rule is definitely enabled

Outlook for Microsoft 365 64-bit Version: 2207 (Build 15427.20210 Click-to-Run)

Thanks,

Jonathan

Answer 1

Hi @Jonathan / Spud ,

Welcome to our forum!

Based on my test, i found that when clicking "Run Rules Now...", the rule doesn't work, but when an email from the domain arrives, the rule works, which is the same issue as yours. In addition, i also tried to select "Run this rule now on messages already in "Inbox", it fails too and prompt this:

So i'm afraid that the rule will work when it is always enabled but not when it is ran manually. It's by design.

---

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".
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.