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I have a bunch of rules in Outlook. Until last week they all worked fine, but now they don't get automatically applied upon incoming mail. When I manually apply rules now from Rules menu, they get executed. What might cause this?

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Outlook is often flakey with rules.

Have you installed any 3rd party add-ons or applied patches to Outlook recently?

If you have the first thing I would do is uninstall anything you have added and see if the rules work again.

I have had this issue before with .pst and .ost files.

I've had to run Scanpst.exe (see here for more details on it: in the past and it's resolved issues.

I've uninstalled patches, run the scanpst.exe tool and then re-installed patches and it's worked.

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Another option would be to Export your set of rules. Delete them from your list, Restart outlook and them import them back. Here is a good article on this:

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