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Level 8 of the Stripe CTF is a password server that returns success: true if and only if the password provided matches the password stored directly via a RESTful API and optionally indirectly via a callback URI. The solution is side channel attack like a timing attack but with ports instead of time.

(I found this in my drafts folder and had intended to post a while ago.)

Code

    def nextServerCallback(self, data):
        parsed_data = json.loads(data)
        # Chunk was wrong!
        if not parsed_data['success']:
            # Defend against timing attacks
            remaining_time = self.expectedRemainingTime()
            self.log_info('Going to wait %s seconds before responding' %
                          remaining_time)
            reactor.callLater(remaining_time, self.sendResult, False)
            return

        self.checkNext()

Issue

The password server breaks the target password into four pieces and stores each on a different server. When a password request is sent to the main server it makes requests to the sub-servers for each part of the password request. It does this in series and if any part fails, then it stops midway through. Password requests may also be made with corresponding URI callbacks and after the server decides on the password makes an HTTP request on the provided URI callbacks saying if the password was success: true or false.
A timing attack looks at how long it took for a password to be rejected and longer times could mean a longer prefix of the password was correct allowing for a directed brute force attack. Timing attacks are prevented in this case by code on the password server that attempts to wait the same amount of time, even if the first sub-server responds with false. However, the server uses sequential outgoing port numbers shared between the requests to the sub-servers and the callback URIs. Accordingly, we can examine the port numbers on our callback URIs to direct a brute force attack.
If the password provided is totally incorrect then the password server will contact one sub-server and then your callback URI. So if you see the remote server's port number go up by two when requesting your callback URI, you know the password is totally incorrect. If by three then you know the first fourth of the password is correct and the rest is incorrect. If by four then two fourths of the password is correct. If by five then four sub-servers were contacted so you need to rely on the actual content of the callback URI request of 'success: true' or 'false' since you can't tell from the port change if the password was totally correct or not.
The trick in the real world is false positives. The port numbers are sequential over the system, so if the password server is the only thing making outgoing requests then its port numbers will also be sequential, however other things on the system can interrupt this. This means that the password server could contact three sub-servers and normally you'd see the port number increase by four, but really it could increase by four or more because of other things running on the system. To counteract this I ran in cycles: brute forcing the first fourth of the password and removing any entry that gets a two port increase and keeping all others. Eventually I could remove all but the correct first fourth of the password. And so on for the next parts of the password.
I wrote my app to brute force this in Python. This was my first time writing Python code so it is not pretty.

To setup my home Windows dev box to be accessible from outside I followed two main steps:

•  Configure my router to forward the remote desktop port.
•  Setup a free dynamic DNS service.

Last time I had to do this there was a service named dynamicdns.org which seems to still exist but no longer appears to be free. Instead I used dnsdynamic.org which is free and has a web API as well as links to and instructions for setting up native tools to dynamically update my IP address.