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I'm running into a couple networking issues which I suspect could be related to SSL/TLS, but I'm not sure how to go about confirming that that's the case.

The main problem I'm having is I'm unable to fetch gem dependencies from rubygems.org (e.g. using Bundler).

One reason I suspect this could be SSL-related is that at about the same time, I also started experiencing very slow connection initialization when using weechat to connect to freenode. It tends to time out on the first connection attempt, though it retries and eventually succeeds.

I'm running NixOS 18.03, with Gnome. I dug around a little with journalctl -k but didn't see anything while attempting to fetch from rubygems.

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I'll blindy assume that fetching dependencies would take place over http. You could use openssl's built-in command line tool to connect yourself:

openssl s_client -connect that.ruby.host:443

and Ctrl-D out of that. (My crystal ball guess for "times out first, then succeeds" is that possibly there's a nearest-mirror mechanism in there and the one host is broken in some way; my routine guess would be IPv4 vs IPv6 troubles.)

  • Fetching dependencies from rubygems.org does take place over http/https (both are supported, though both are failing for me). I was able to connect with openssl s_client -connect rubygems.org:443. Does this indicate that the problem is not related to ssl/tls? – ivan Apr 25 '18 at 13:12
  • @ivan: yes, that does indeed sound like it's not a TLS problem. – Ulrich Schwarz Apr 25 '18 at 14:44

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