I spent several days investigating an error that was coming up with our Rails application build using jRuby v9.3.3 - v9.3.10. Everytime the build would try to run bundle install we would get the following error.

Fetching source index from https://rubygems.org/
Retrying fetcher due to error (2/4): Bundler::HTTPError Could not fetch specs from https://rubygems.org/ due to underlying error <Unrecognized SSL message, plaintext connection? (https://rubygems.org/specs.4.8.gz)>

Retrying fetcher due to error (3/4): Bundler::HTTPError Could not fetch specs from https://rubygems.org/ due to underlying error <Unrecognized SSL message, plaintext connection? (https://rubygems.org/specs.4.8.gz)>

Retrying fetcher due to error (4/4): Bundler::HTTPError Could not fetch specs from https://rubygems.org/ due to underlying error <Unrecognized SSL message, plaintext connection? (https://rubygems.org/specs.4.8.gz)>

Could not fetch specs from https://rubygems.org/ due to underlying error
<Unrecognized SSL message, plaintext connection?
(https://rubygems.org/specs.4.8.gz)>
ERROR: bundle install failed

You will notice it attempts 3 times, this is because the script is actually running:

bundle install --local --retry 3 || { echo "WARNING: bundle install --local failed, running bundle install"; bundle install --retry 3 || { echo "ERROR: bundle install failed"; exit 1; } }

When we would run our script from the command line, it would work just fine. When we would try to run it from our Bamboo application (used for Continuous Integration), it would fail with the above errors.

We’re using RVM to manage the different Ruby versions needed by our applications on the Bamboo server. We thought it might be an issue with Bundler, but it turned out that one of our JAVA configurations was causing this issue.

We noticed that JAVA_OPTS was not set when our admin ran the build scripts from the command line, but with the Bamboo job it was set, and it included the -Djava.security.properties option pointing to a file that used the following:

jdk.tls.disabledAlgorithms=SSLv3, RC4, DES, MD5withRSA, DH keySize < 1024, \
    EC keySize < 224, 3DES_EDE_CBC, anon, NULL, RSASSA-PSS

When we added this to the export for JAVA_OPTS, the issue occurred when running the build scripts, or when running the RubyGems troubleshooting script (curl -sL https://git.io/vQhWq | ruby). When we removed it, the error returned.