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I have to constantly delete my sents because I send about 10 video clips (6 MEG each) per day, thus I am always filling up my free storage that Google allows. That's fine with me, I don't need to keep those sent files. What I do need to keep are files with attachments that I send myself (from other computers) so that I can keep them in labels in my iPhone and iPad gmails for future use forever. (This is all under my one gmail account.). But if I select all my sents, my labeled emails also get deleted. How can I stop this or find a work around? It's painstaking (takes about 45 mins each time) to go thru each of my sents and check the ones I need to keep and the ones I can get rid of, so I'm wondering if there's another workaround rather than that obvious one. (Yep, I send hundreds of emails per day.). Thanks!

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To delete a subset of email from your sent mail while avoiding those emails you sent to yourself do the following.

  1. You will need to execute a search, this can be entered in the search bar:

    is:sent to:(-youraddress@gmail.com) has:attachment
    

    Note: the minus sign is crucial.

  2. You should now see all the messages that met the criteria, you sent it, but not to you, and there is an attachment. It will show you 20 messages at a time. I don't know of a way to expand this beyond 20 at a time

  3. Scan the list and if it looks OK delete them.

  4. If you have enabled Quick Links from gmail labs you can add the search string as a quick link so you don't have to remember the syntax of the search string.

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Edited the query to make it in line with the OP's request (delete emails with attachments sent to self). –  dnbrv Jul 8 '12 at 1:03
    
I had to edit it back: the key phrase is "need to keep are files with attachments that I send myself". Therefore the search had to be for messages that I didn't send to me, then delete those messages. –  mhoran_psprep Jul 8 '12 at 2:10
    
Hmm. The wording is a bit weird. I thought the OP wanted to delete the 2nd copy of the email. –  dnbrv Jul 8 '12 at 4:52
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