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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