How to Fix Outlook Rules Not Working
Edit and rename your Outlook rule. If your rules have lengthy names, editing them to have shorter names could decrease the size of your existing rules.
Delete old rules. Another way to reduce the overall size of your existing rules is to get rid of those you no longer need.
Clear the Client only or on this computer only checkbox. It's possible that when the rule was created, this setting was selected, which will prevent the rule from working when you access your Outlook account on a different device.
Manage a large number of rules by combining similar ones. Turning several similar rules into a single rule is another way to reduce the overall size of your rules. After you've combined similar rules, delete the unnecessary rules.
Rename or reset the SRS file in Outlook. The SRS file contains the settings you set through the Send/Receive dialog in Outlook.
Reset your rules and test your mailbox for corruption if you're using a POP3 or IMAP account in Outlook. Start by deleting the rule that's not working, then run the Inbox Repair Tool.
Fix corruption using an Exchange account. Turning on Exchange Cache Mode could give you a smoother experience when you connect to your email account because a copy of your mailbox saves to your computer. This local copy offers quicker access to your email messages and other items.
Hope This Helps,
Peter