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Folks, I've heard that wireshark might help with this challenge, but I've never used it and could not find it discussed readily in the docs or past forum questions (which surprised me): I'm simply wanting to detect if I am sending/receiving unencrypted communications from my computer--such as when (for some reason) I can't enable my vpn software while on a public wifi.

I sense that that was more of a worry in years past when https was not common, along with using tls for smtp logins, etc. Still, since some apps or tools may well still communicate unencrypted, I'm wanting to detect that. I'd really have thought it might have been discussed here, so I was surprised not to find an answer more readily. Feel free to point me to a resource if it exists.

To be clear, I'm hoping not to have to look at every connection establishment to determine if it IS using an encryption approach: Instead, I was hoping it may be possible somehow for w/s or any other tool to simply watch the outbound (and inbound) communications to detect and warn when it IS unencrypted.

I appreciate that may not be at all possible with w/s. Indeed, someone may want to tell me this is a foolish idea because of some underlying aspect of how things work, such that no tool could possibly help. Still, I wanted to ask as much to help others who may come with the same question in the future--whether the answer is encouraging or discouraging.