Following my comment, and even though it's a bit different from what you ask: I really enjoyed the story here where the use of an incorrect pseudorandom number generator led to the arrest of members of a "russian espionnage network". Disclaimer: I have no idea how truthful all of this is, I'm leaving you the task of checking how serious the book "compromised" is (that's the book this blog post is based upon, I did not read it).
Roughly, a very stupid PRG was apparently used to create "filler transmission", in order to hide when an actual transmission was happening. The trouble is, this broken PRG was producing decimal digits from 0 to 8 - i.e., you never had any 9! This observation allowed the FBI to distinguish transmissions from fillers, which opened the door to a traffic analysis. Eventually, they identified that communications were happening periodically for a fixed duration, always at the same time slot, and correlated that with the schedule of suspects (e.g. observing that they were never out of their home when a communication was happening), which led to their arrest.
There is also a lot of documents on the VENONA project, which was dedicated to decrypting encrypted transmissions where a one-time pad was reused, you'll find plenty resources on this one online.