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My boss has asked me to look into this question but I'm not sure where to begin to research it.

Any tips on the types of topics I should be looking into?

A: 

As mentioned in another comment, more details on the problem would be useful. But in principle the problems can occur on every layer, especially character encodings, BigEndian vs. LittleEndian and so forth.

In addition these two books I can highly recommend:

  • Tanenbaum: Distributed Systems
  • Tanenbaum: Computer Networks
DaDaDom