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As of this update Iām running into an issue with a Ruby gem (coveralls-lcov) that uses Net:HTTP to perform a POST, it is failing with an SSL error and this appears to be related:
opened 01:48AM - 04 Oct 25 UTC
closed 07:46AM - 06 Oct 25 UTC
The following example fails after installing "OpenSSL 3.6.0":
```ruby
require 'ā¦ net/http'
require 'uri'
uri = URI('https://example.com')
# Creating a POST request, which is a subclass of Net::HTTPGenericRequest
request = Net::HTTP::Post.new(uri)
# Sending the request
Net::HTTP.start(uri.hostname, uri.port, use_ssl: true) do |http|
response = http.request(request)
puts response.body
end
```
With the following error:
```
/Users/[user]/.local/share/mise/installs/ruby/3.4.6/lib/ruby/3.4.0/net/protocol.rb:46:in 'OpenSSL::SSL::SSLSocket#connect_nonblock': SSL_connect returned=1 errno=0 peeraddr=[2600:1406:5e00:6::17ce:bc12]:443 state=error: certificate verify failed (unable to get certificate CRL) (OpenSSL::SSL::SSLError)
from /Users/bfolkens/.local/share/mise/installs/ruby/3.4.6/lib/ruby/3.4.0/net/protocol.rb:46:in 'Net::Protocol#ssl_socket_connect'
from /Users/bfolkens/.local/share/mise/installs/ruby/3.4.6/lib/ruby/3.4.0/net/http.rb:1736:in 'Net::HTTP#connect'
from /Users/bfolkens/.local/share/mise/installs/ruby/3.4.6/lib/ruby/3.4.0/net/http.rb:1636:in 'Net::HTTP#do_start'
from /Users/bfolkens/.local/share/mise/installs/ruby/3.4.6/lib/ruby/3.4.0/net/http.rb:1625:in 'Net::HTTP#start'
from /Users/bfolkens/.local/share/mise/installs/ruby/3.4.6/lib/ruby/3.4.0/net/http.rb:1064:in 'Net::HTTP.start'
from test.rb:10:in '<main>'
```
`bundle doctor --ssl` fails with:
```
The Gemfile's dependencies are satisfied
Here's your OpenSSL environment:
OpenSSL: 3.3.0
Compiled with: OpenSSL 3.6.0 1 Oct 2025
Loaded with: OpenSSL 3.6.0 1 Oct 2025
Trying connections to https://rubygems.org:
Bundler: success
RubyGems: success
Ruby net/http: failed
Unfortunately, this Ruby can't connect to rubygems.org.
Below affect only Ruby net/http connections:
SSL_CERT_FILE: exists /opt/homebrew/etc/openssl@3/cert.pem
SSL_CERT_DIR: exists /opt/homebrew/etc/openssl@3/certs
Your Ruby can't connect to rubygems.org because you are missing the certificate files OpenSSL needs to verify you are connecting to the genuine rubygems.org servers.
No issues found with the installed bundle
```
And this
opened 07:33AM - 06 Oct 25 UTC
branch: master
triaged: bug
severity: regression
branch: 3.6
We tried connecting to AWS CLI, LaunchDarkly, and Bugsnag. All of the connectionā¦ s are failing with the below error:
```
#<OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 peeraddr=54.208.14.64:443 state=error: certificate verify failed (unable to get certificate CRL)>
```
I am not an expert in OpenSSL. Please let me know if I can enable verbose and provide more logging to help.
After digging through the above issues, it seems that the fix for the current macOS environment on Circle CI (OpenSSL 3.6.0 and Ruby 3.4.6) is to explicitly add OpenSSL to your Gemfile as this should be fixed in 3.3.1 of the openssl gem (Ruby 3.4.6 is bundled with 3.3.0).
It might be helpful if CircleCI could update their images to include this version of the openssl gem by default?
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Apple Silicon VM Image Info 