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Vulnerability Messenger/Hotmail Affected Messenger/Hotmail Description Gregory Duchemin found following. The problem described below is still working on the latest MSN client version currently available. A bug in the Hotmail Messenger cryptographic system may allow the recovery of millions of hotmail mailboxes's password. Microsoft MSN messenger is a very handy little win32 application designed to keep in touch with friends, family, collaborators around the world. It offers many nice features like real time chats, hotmail mailbox access, etc... Messenger runs with its own protocol to communicate with a bunch of Microsoft dedicated servers and authenticate itself with the same password than hotmail is using (through the global passport system). The password is not sent clearly on the wire but hashed with MD5 in the following manner. While negociating a connection with a remote Microsoft server, msn clients clearly send the target user mailbox to be authenticated with (basically the username) and get back a scrambler string to be prepend to the password before hashing it and sending it. client ----- VER xx MSNP5 MSNP4 CVR0 ---------------> MSN server client <---- VER xx MSNP5 MSNP4 CVR0 --------------- MSN server client ----- INF (xx+1) ----------------------------> MSN server client <---- INF (xx+1) MD5 ------------------------ MSN server client ----- USR (xx+2) MD5 I ----------------------> MSN server client <---- USR (xx+2) MD5 S yyyyyyyyy.yyyyyyyyy -- MSN server (the scrambler string is actually made with seconds.microseconds) client ----- USR (xx+3) MD5 S xxxxx...(32 chars) ---> MSN server Here it is, the password hash has been sent and may be easily broken by bruteforcing it. The hash creation process is as follow. Say user toto has a password "titan". Then his client generate the string "yyyyyyyyy.yyyyyyyyytitan" and the according MD5 hash, say xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx. The client send MD5(yyyyyyyyy.yyyyyyyyytitan) on the wire. By sniffing the wire, a malicious user can obviously retrieve the scrambler string and the final hash. Then he can start a bruteforce session trying all password combinaisons with the same scrambler prepended and comparing the resulting hash with this he previously sniffed. (an exhaustive attack) Basically, without any bug, messenger is already vulnerable because of the weak cryptographic scheme it uses. Gregory wrote, with the great help of Simeon Pilgrim, a very fast MD5 bruteforcer designed to use scrambler strings to finally retrieve an original password for a given MD5 hash. Currently it takes only 12 days to exhaust all 8 chars length passwords in the charset [a-z0-9] with an average speed of 2 600 000 hashes sec with only one 1 Ghz athlon processor. (we considere to be able to test up to 4 000 000 hashes/sec with the next release and one 1.3 Ghz processor). Win32/Unix versions are freely available at http://mdcrack.multimania.com Another important point is that, if nowadays users can't actually choose a new password lesser than 8 chars length, all old and weak passwords (from 1 to 7 chars) are still in use and just works perfectly with MSN. How many users are currently at risk? Too much! The last point is a nasty bug in the client implementation that allow a malicious user, spoofing the MSN server, to send a (NULL) scrambler string. In such a case and intead of simply closing the connection, the client send the mere password hash making things even faster for a further bruteforce attack. client <---- USR (xx+2) MD5 S ---------------------- fake MSN server client ----- USR (xx+3) MD5 S xxxxx...(32 chars) ---> fake MSN server where xxxx...(32 chars) is actually MD5(password). Note that if this technic is still stealthy, it may need, in some network topologies, the use of icmp redirect/ arp spoofing to redirect all the flow to the attacker machine inside a given network. But this kind of attacks are well known by networks crackers. Note that all communications between clients and servers are in a clear form, and by the way, many other identity robbery attacks remain available for instance, when our victim is asking messenger to open his mailbox, the malicious user may send another URL to the client like a spoofing site with a false hotmail relogging page. Because hotmail and MSN are using the same authentication system called passport, compromising users MSN account is finally the same trick than compromising hotmail users mailbox. A malicious user with a freshly hacked MSN password can use it either with messenger or with www.hotmail.com Because a tremendous number of people are using these services without taking too much care about their password strongness, the number of potential victims is really great. The attack described above can be released from any place in the path between the victim and MSN servers or simply in the same network, this is the mere prerequisite. It seems that the main problem here is that the exhaustive keysearch attack has been shown to be possible for small keys within a reasonable length of time on cheap hardware. This is nothing terribly new, everyone has been cracking passwords and keys for ages, and will keep on doing so, the advent of cheap high performance computers has just made it quicker and easier to have a go at it yourself. This doesn't help things like MSN messenger which were built with fairly weak authentication schemes, where the strength of the scheme was never really seriously questioned. Whoops. Solution Choose a quite strong password (at least 9 chars length with a good charset) and change it as regularly as possible. Finally, never never trust hotmail and any other web based free accounts for you very own mails. The solutions seem a bit obvious: 1. Increase the size of the keyspace and enforce those limits. 2. Increase the entropy within the keyspace and provide enforcement mechanisms 3. Rotate keys over periods short enough that a exhaustive attack is impractical with a given time with given resources. 4. Wrap the authentication process up inside a tunnel using SSL There are however some fairly serious problems with all of these: 1-2 Mean forcing users to pick longer and more complex passwords. This probably means more people will choose the 'remember my password' option when given to them. This is probably not a good idea if the machine that is doing the remembering isn't terribly secure for reasons we shouldn't have to explain. 3 is is just plain old impractical for something like Hotmail, with a userbase of several million people some of whom only check their mail there once every couple of months. 4. Would mean redesigning and then pushing new clients to everyone signed up, as well as extensively re-engineering the client. Not easy, and potentially costly. This is also the most likely fix as it imposes a one time overhead on the user to upgrade their software. This still doesn't fix the remember my password problem, but would make people less likely to use it as they could still use their old weak easy to remember passwords albeit in a nominally secure environment.