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I have many rules enabled in my Outlook 2007, many rules fail and get disabled this creates a mess in my inbox. Is it possible for me automatically enable rule after it fails due to an offending email ?

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Have you thought about looking at the rule to see why it fails and see if you can work around it? :/ – William Hilsum Sep 15 '11 at 13:26
Sometimes it fails as the message has attachment. Most of the time I am clueless why the rules fail – Ravi Gupta Sep 15 '11 at 13:30
it also fails if you have too many rules how many rules have you setup? – ben950 Sep 15 '11 at 14:27
I have 64 rules set up in my outlook 2007 – Ravi Gupta Sep 28 '11 at 13:52

Have you upgraded to Outlook 2007 from a previous version ?
If so, you might need to recreate the rules that fail.

The following Microsoft article states that there is a limit on the total textual length of the rules, which might be as low as 32 KB. If you have many long rules, you could be hitting this limit :
Some rules are disabled, and you receive an error message when you try to enable them after you upgrade to Outlook 2010, to Outlook 2007, or to Outlook 2003

The article Troubleshoot rules also says :

If you see the word "failed" in the name of your rule, it means that Outlook was unable to successfully import your entire rule. The most common cause of import failure is that the rule is too complex; for example, it has too many conditions. You should examine and manually modify these rules.

Another article explains why a rule that forwards mail to the Internet may fail if you are connecting to an Exchange server.

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