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I am working on a local area chat application which would simply establish connection between two sockets on the LAN and proceed with communication. Now focusing on security, my main concern is to prevent my application from data leakage due to successful mitm attack.

  • In web there is certificate verification, but I don't have any dedicated server, as it can be simply communication between the only two nodes on network.
  • The closest question was this - Preventing man in the middle attack, but adding a static entry in ARP table is neither viable nor feasible in my case.
  • updated answer,.. – davidb Jan 7 '16 at 10:28
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You can't create an application in a way it's not vulnerable to MiTM attacks because these attacks happen an a lower layer than your application works on. You can only secure the network which is used by the clients. There are several countermesures available. First you need port security which will prevent many of these attacks. Then you could add a net based IDS/IPS which is capturing the monitor port of your switch. But all of this wont come for free it will cost you some money and a lot of time.

// The more practical solution is to use encryption to ensure that someone who performs a MiTM attack isn't able to read the data he captures. But even this won't give you 100% security. The main problem here is that you dont have a server.

Async encription (SSH like)

On both sides you create a RSA key pair and then use this to encrypt and decrypt messages. When the first connection is established between two hosts you save the key of that host to identifiy this host in further sessions. The problem here is that a MiTM-Attacker might interrupt the first session. He is then in a position where he can inject his own certificates to perform a MiTM attack anyway. This will also lead to a sitiuation where in further sessions that aren't interrupted by the attacker the connection will be recognized as insecure because the saved key of the opossing host is in fact the one of the attacker.

Your problem her is that you don't know the key of the opossing side until you connect for the first time. Many companies solve this issue when it comes to ssh by syncing the ssh_known_hosts via a trustworthy server. You dont have such server because of that you can't do this here and you are kind of insecure at the first connection.

Pre-Shared-Key

You can implement encryption with a pre-shared-key but the problem here is always the useability and the user behaviour. When you generate a PSK for every connection then the key must be exchanged. Always remember: People are lazy. They will send the PSK via mail which is potentially unencrypted. Also many people might say "ohh thats to complex I will use another software that is easy to use" and this is how people end up with easy to use but totally insecure software.

// Also none of the described proceedures will prevent a MiTM-Attack they will only prevent the attack from being successful in the way it was ment to be.

  • Well thanks a lot, as far as adding a IPS/IDS is concerned, it's not viable as I am trying to target my audience with a small standalone chat application. As far as encryption is concerned I too had thought about that exactly but I too dropped this when considered that it could be bypassed in case mitm attack is performed at first connection only. So ultimately I think there is no way for complete security... Thanks anyways... Will accept your answer in a while if no other answers come... – Kaustubh Jan 6 '16 at 19:56
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    TLS mutual auth on properly secured systems would prevent pretty much any MITM attack. – Jesse K Jan 6 '16 at 20:54
  • @kaustubh - see Jesse's comment, he has a solution. – Neil Smithline Jan 7 '16 at 3:22
  • I will edit my answer in the next two hours to Clear Things up. – davidb Jan 7 '16 at 6:56
  • @JesseKeilson I don't have a central permanent server so with TLS mutual auth too is vulnerable with easy forging,... – Kaustubh Jan 7 '16 at 14:37
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Just to add to @davidb 's answer, you only need a preset symmetric key for doing encrypted communication, which should be simple enough. If this doesn't work, you can use a certificates signed by your own CA which both client/server are aware of, and facilitate secure communication.

  • thanks but I don't have a dedicated serve so certificated can b easily spoofed, and I don't have any fixed number of users or so, so can't have preset symmetric keys :(.... Ultimately falls down to that there is no way to successfully prevent data leakage if the attacker is active from first connection ... – Kaustubh Jan 7 '16 at 14:43

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