Reading sniffer GMAIL traffic

Posted on 2008-11-11
Last Modified: 2012-05-05
So we have a sniffer capturing all network data to protect proprietary info.  Corporate email is easy to monitor since we operate that server.  Users still have personal gmail accounts -- and all those captured packets look like gobbledygook.  If a gmail user (assume not https, just http) sends an email saying "our top secret ingredient is chili peppers" why can't I find those packets in my EtherDetect Packet Sniffer?  When I test it by sending my own gmail account, I don't find any packets with clear text in them.  Is gmail using some new kind of encryption that isnt https but somehow in the body, they are doing all this encryption?
Question by:cglenn3932
    LVL 5

    Expert Comment

    I would imagine that the folks are Google are security- and bandwidth-conscious enough to compress, if not encrypt, data, even if it's not sent over a secure HTTP connection.

    Author Comment

    They do gzip compress, but my sniffer supposedly uncompresses gzip stuff.  They do not encrypt because that would cost millions--heck billions of dollars in additional server costs.  You can use https or turn on encryption, but default is off (and my tests were using OFF).
    LVL 7

    Expert Comment

    Hi Dear
    As Gmail bydefault Operates on SSL so that data you will get with sniffer will be encrypted and no useful information will be available. all files that are uploaded into gmail or hotmail are sent as encrypted data to server.
    As Bydefault Gmail Uses HTTPS, so if you block that and force users to use HTTP. then you can sniff the usefull data.
    LVL 13

    Accepted Solution

    >> They do gzip compress, but my sniffer supposedly uncompresses gzip stuff

    But if they password protect their archive, there is no way your sniffer can uncompress it.

    >> When I test it by sending my own gmail account, I don't find any packets with clear text in them.

    It does not mean that it's encrypted. It could just be encoded in some format, maybe Base64.
    Contrary to what others have said, Gmail does NOT encrypt email.

    SSL is use ONLY during login. Pay close attention to the little security padlock in your browser.
    You can however ensure that the entire session is encrypted by using this instead to login to your Gmail:

    My advice is that a network sniffer is hardly the right tool to use against coorporate data theft. There are just too many areas you cannot handle.
    Take for example, you sniff all web mail traffic (yahoo/hotmail/gmail). All I need to do, is zip up my document, password protect it and send it through (most good archiving software use AES encryption by the way).
    All you'll see is garbage.

    A better option (but still not 100% full proof) is to invest in a Data Loss Prevention (DPL) solution.

    I'm particuliarly impressed with McAfee

    But they still have a hard time with zip archives. Although you can set policies which block all zip archives from being sent out via web mail

    Hope that helps
    LVL 4

    Expert Comment

    There is an option in GMail to enforce SSL through entire session.  Although, that doesn't prevent being able to carry the cookie over into other less secure google applications.

    Expert Comment

    Couldn't you just control access to the website using your proxy or firewall?  You could also block this using DNS redirects to an internal cul de sac website stating that the Internet is to be used only for business use.

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