Run Outlook 2010 Rules from Sent Items

Hello I am trying to figure out a way to delete a message from my sent items automatically.

I have the rule created that looks for the criteria and if i have the sent items open when i edit the rule I have the option via a check box to select " Run this rule now on messages already in "Sent Items" "  and the rule works fine, deletes the message without any problems...

However i can’t figure out how to have the rule run automatically when I am not in the editing dialog box.

Thank you,
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Vanguard_LHConnect With a Mentor Commented:
Not using the stop-clause in your rules means more than one rule gets exercised against the same message.  This can have side effects.  For example, you might have one rule move a message to a folder but a following rule moves it to a different folder.  That may be what you want but you have to consider the flow of the message through multiple rules and which ones will fire on that message.

It is a pity that Microsoft chose the phrase "move a copy" rather than just "copy".  It has confused many Outlook users who see the "move" part of the phrase without seeing the "copy" part of it.  The rule will act no differently when ran manually than when ran automatically yet you claimed the rule behaves differently when ran manually.  You said the rule actually deleted the original message.  For inbound rules, there are "delete it" and "permanent delete it" clauses you can add to a rule.  For outbound rules, there is only "move a copy" because the assumption was made by Microsoft that you always want to keep a copy of your sent e-mails for later reference.

If you want to delete old items out of a folder, look into using the auto-archive feature of Outlook.  You can configure when auto-archive gets run (as the global option) and when items become eligible for archiving (as the folder property).  You can have the item permanently deleted or moved into an archive file (archive.pst).  If you use File -> Open to load the archive.pst file, it appears as a separate tree in Outlook (because it is a separate message store).  That way, you can still go find those old items.  With the archive.pst file loaded in Outlook, you can even configure its auto-archive settings on each folder to permanently delete its old items.  So you could archive, say, 1-year items from your message store into the archive file and permanently delete 5-year old items in the archive file.  In fact, you can chain the archives together.  You could configure auto-archive on your message store to archive items older than 1 year into archive.pst and use auto-archive on archive.pst to archive over 2-year old items into archive2.pst and use auto-archive on archive2.pst to archive over 3-year old items and so on with the last archive file in the chain having its auto-archive folder settings set to permanently delete the N-year old items.  The only caveat is that all of the archive files must be loaded in Outlook (they'll appear as separate message stores) so Outlook can actually exercise its archiving function against them.  I archive items older than 1 year and permanently delete items out of the archive file that are over 5 years old.  Obviously I don't archive the Deleted Items or Junk folders.  I use auto-archive on those to permanently delete items over a week old.

I believe for a custom action that you have to write a VBA macro which you can call using this clause.  I don't know if you want to get into learning VBA or trusting some unknown author to give you the code along with the procedure to add it to Outlook.  Instead you might want to use some 3rd party add-on to Outlook to organize your sent items (if auto-archiving doesn't do what you want), like SperrySoftware's Sent Items Organizer (never used it and don't know if it will do what you want).  Mapilabs also has several Outlook add-ons but their site (its gateway) is down right now so I can't go look to see what add-on might apply to you.
Are there other rules positioned before this one?  Might they trigger on the same message?  If so, do they have the clause to not run other rules?  If the stop-clause is included in a rule that fires then further rules do not get exercised on the same message.  Usually you do want the stop-clause included in a rule unless you want to OR several of them together.  With the stop-clause included, the ordering of rules is important: they are executed in the top-down order as listed.  You have to consider the "flow" of the message as it traverses through the rules and the actions taken against it as it gets tested by each rule in the order they are listed.

Is the rule you want to fire actually enabled?  You can define a rule but leave it disabled.  Running a rule manually means you want to run it whether it is enabled or disabled.  The rule has to be enabled for automatic execution.

Was the rule defined to be an outbound rule?  That is, was it defined to exercise against *sent* messages (versus received messages)?  Does the rule start with "Check messages when they arrive" or with "Check messages after sending"?

What does the outbound rule look like?  What are its conditions?  What other rules are defined before it?  Are there other outbound rules?
FredDavAuthor Commented:
Thank you for your reply,

This rule is at the very top of my list of rules and i was not using any stop clause in any of my rules. I also do have this rule enabled.

After more testing I think i am running into a limitation of outlook as it does not seem that Outlook 2010 supports the actual DELETION of a message when you start the rule with "Apply this rule after i send the message" so what i was actually seeing was the message getting copied to my deleted bin, but the original message was still in the sent items folder.

The rule originally looked like this:

Apply this rule after i send the message.
with <specific words> in the body
  and which has an attachment
Move a copy to deleted folder                <-- that is the problem "move a COPY"

So what i have done as a work around is replace the last line with "assign a category" and manually looks at the sent items and sort by that category every so many days.

i did see a option in the sent item rule that talks about "perform a custom action"  i suspect that if a application was written to delete message that i could insert that and have the custom action delete the message.

FredDavAuthor Commented:
I agree, that phrase they use is not very good.  

Thank you for suggesting the archive PST file, however the reason for wanting to delete these messages is to actually delete them since i will no longer need them (not even a copy) after i delete them.

I took a look at the alternative suggestion that told me about the SperrySoftware organizer, however i think i found a better one that will suit my needs. I did some searching after you suggested the one above and i found this one:   seems very robust and has a ton of features.

Thank you very much for your time in trying to answer my question/problem.

Just as a reminder about the auto-archive feature.  You can have it permantly delete items older than the specified number of days.  I use auto-archive on my Junk and Deleted Items folders.  I don't want to archive a copy of anything in these folders.  I do want to get rid of old items.  Also, in my archive.pst file (which gets loaded when Outlook loads), I use auto-archive to delete items over 5 years old (except for a couple of work-related folders).  That way, my archive file doesn't get too big and I have yet to need or reference non-business e-mails over 5 years old.  If you're trying to keep your Sent Items folder clean of old items, auto-archive will work for that.

Glad you found a plug-in that does what you want.  Auto-Mate is $10 (30%) more expensive than SperrySoftware's Sent Items folder.  I haven't done a point by point comparison of these plug-ins (don't use either of them) but it looks like Auto-Mate is more robust or maybe it just seems easier to see how to use it.  Just in case you haven't bought either of the payware plug-ins yet, there might be some code for a VBA macro you could install into Outlook that does what you want over at, or you could ask for help over there and someone might write something up for you.  Stuff there is free.
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