We have the same problem with Bitcoin. On one hand we'd love a system that automatically collects a stack trace, memory dump, information about the environment on a crash and sends it to us (like Google Breakpad does). On the other hand it opens a whole can of worms if accidentally a private key is sent. Encryption is no solution in this case; the data still is stored somewhere which could be compromised. It's very hard to automatically collect diagnostic data without potentially collecting sensitive data...