Instant Messenger is one of the most popular communication service when translating message or data each other through Internet. For digital crime investigation, therefore, it is obviously important to obtain communication trace and contents derived from Instant Messenger. This is because that gathering traditional communication histories also have been important until now. However, extracting communication trace and contents are not easy because they are generally encrypted or obfuscated in local system, futhermore, sometimes they are located at server computer for Instant Messenger. This paper researches on extracting communication histories against NateOn, BuddyBuddy, Yahoo! messenger and Mi3 messenger, and obtaining user password or bypassing authentication system to Instant Messenger Service when a user use auto-login option.