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If a given software can't handle TLS it's a fundamental problem of the software / development process and not the fault of the infosec community. Update/change the used libraries and everything will be fine. I've switched a whole distributed system from plain communication to TLS secured connections just yesterday.

Yes sometimes it's pain to solve some TLS based errors and I also miss the opportunity to debug each transmitted packet with tcpdump but I also appreciate it that the continuous focus on TLS improves the tooling and libraries and each day it get's a little bit easier to setup a secure encrypted connection.

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