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I have an Outlook 2007 rule set up to reply to sender with a custom reply template if the subject or body contains specific text. This rule works the first time for a specific sender, but doesn't work if the sender sends me another email in the same day. I even confirmed this by setting my PC clock ahead by a day. Sure enough, the auto reply was sent successfully. This tells me that there is something in Outlook that's specifically keeping auto-replies from going out in the same day to the same sender.

I am aware that perhaps this is a preventative measure to keep two machines from entering a feedback loop with one another, but I want to circumvent whatever is causing this so that my rule works unconditionally every time even if it's 100 times a day.

Update: I've discovered that it's not only per day, but per running instance of Outlook. This means you can have your rule send out an automatic reply, shut down/restart Outlook, and have it send out another auto reply. If it's in the same instance, though, it won't work. There has to be a way around this. Maybe the answer lies in VBA, an option I am about to explore.

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if you found the answer, you should rewrite the question and post the answer. Thats what this site is for. :) –  Keltari May 12 '13 at 2:43
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if you've found an answer, post it as an answer. I don't understand why you have to delete it without sharing the answer –  Sathya May 12 '13 at 7:39
    
Is this an Exchange account? –  Oliver Salzburg May 12 '13 at 10:30
    
@Sathya: SE allows users to delete their own questions. The only reason I can't now is because I added bounty. If I had just researched a few hours longer before doing so, I would have been able to delete this question and you wouldn't have had a word to say about it. At any rate, I didn't really find an objective answer, just hints that it can't circumvented. I've decided to write a VBA macro that does this, but, by the time I get around to it, bounty will have already been systematically awarded to a random, lucky answerer, thus resulting in a misleading Q&A which is bad for SE. –  oscilatingcretin May 12 '13 at 15:03
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In that case, I removed the bounty. You should be able to delete your question if you strongly feel about it. Other than that I don't think there's any harm from keeping it around, even if there's no answer (yet). –  slhck May 12 '13 at 15:53
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2 Answers

Please make sure you don't have a compatibility issue that might be a result of a rule that was "inherited" from a previous version of Office.

Please verify the following:

  1. In ToolsRules and Alerts, in the E-mail Rules tab press Options button (should be the rightmost option)
  2. In the Options window click the Upgrade Now. Although this is considered to be a performance only I think you should try it.

If this has any relevance to your issue or has some beneficial effects please report back.

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My Upgrade Now button is disabled, so I can't click it. –  oscilatingcretin May 12 '13 at 15:08
    
OK, that rules out the compatibility issue. –  user223217 May 12 '13 at 16:33
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up vote 0 down vote accepted

Answering my own question here. My research has pointed me to the fact that this, as I said in my question, is a preventative measure implemented by Microsoft to keep two senders from entering to a spam feedback loop. The only way I know that this can be done is by writing a VBA macro. I have started writing it, but I will not have the time to finish it in this week or next. If I ever do finish it, I will come back here and post it. For now, since the bounty clock is ticking, I am just going to answer this now to close out the issue.

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Nitpick: it's not simply implemented by Microsoft it's written into the standards RFCs that govern the transmission of email, and to which all mail clients and MTAs should adhere. –  Sammitch May 14 '13 at 22:16
    
So auto-replying to an email I receive is against these "standards"? I wouldn't mind seeing some official literature on this. –  oscilatingcretin May 14 '13 at 23:09
    
It's in RFC3834. Enjoy being bored to tears. It basically boils down to: don't autorespond to an autoresponder, don't autorespond more often than X, and set proper headers to indicate that it is an automated response. Not adhering to these recommendations is a quick way to kill a mail server due to autorespond loops. –  Sammitch May 15 '13 at 17:00
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