Reminds me of my favorite bug story from my own career. It was in my first year or two out of college. We were using a commercial C++ library for making HTTP calls out to another service. The initial symptom of the bug was that random requests would appear to come back with empty responses -- not just empty bodies, but the entire response was empty (not even any headers).

After a fair amount of testing, I was somehow able to determine that it wasn't actually random. The empty response occurred whenever the size in bytes of the entire request (headers and body together) was exactly 10 modulo 256, for example 266 bytes or 1034 bytes or 4106 bytes. Weird, right?

I went ahead and worked around the problem by putting in a heuristic when constructing the request: If the body size was such that the total request size would end up being close to 10 modulo 256, based on empirical knowledge of the typical size of our request headers, then add a dummy header to get out of the danger zone. That got us past the problem, but made me queasy.

At the time, I had looked at the code and noticed an uninitialized variable in the response parsing function, but it didn't really hit me until much later. The code was something like this:

  void read_status_line(char *line) {
    char c;
    while (c != '\n') {
      c = read_next_byte();
      *(line++) = c;
    }
  }

Obviously this is wrong because it's checking c before reading it! But why the 10 modulo 256 condition? Of course, the ASCII code for newline is 10. Duh. So there must have been an earlier call stack where some other function had a local variable storing the length of the request, and this function's c variable landed smack-dab on the least-significant byte of that earlier value. Arrrrgh!