Test Slack hooks API from Ruby on macOS

test_slack_connection.rb

#!/usr/bin/env ruby
require 'net/http'
require 'openssl'

uri = URI('https://hooks.slack.com')

puts "Ruby OpenSSL version: #{OpenSSL::OPENSSL_VERSION}"
puts "Default cert file: #{OpenSSL::X509::DEFAULT_CERT_FILE}"
puts "Default cert dir: #{OpenSSL::X509::DEFAULT_CERT_DIR}"
puts

# Test 1: What Ruby sees
http = Net::HTTP.new(uri.host, uri.port)
http.use_ssl = true
http.verify_mode = OpenSSL::SSL::VERIFY_PEER

puts "Testing connection with default settings..."
begin
  http.start { |h| h.head('/') }
  puts "✓ Connection successful!"
rescue OpenSSL::SSL::SSLError => e
  puts "✗ Failed: #{e.message}"
  puts "\nBacktrace:"
  puts e.backtrace.first(5)
end

# Test 2: Disable CRL checking
puts "\n--- Testing without CRL check ---"
http2 = Net::HTTP.new(uri.host, uri.port)
http2.use_ssl = true
http2.verify_mode = OpenSSL::SSL::VERIFY_PEER
http2.ssl_version = :TLSv1_2

# Ruby doesn't have a direct "disable CRL" flag, but we can try skipping verification
store = OpenSSL::X509::Store.new
store.set_default_paths
store.flags = 0  # Clear all flags including CRL checks

http2.cert_store = store

begin
  http2.start { |h| h.head('/') }
  puts "✓ Connection successful without CRL!"
rescue OpenSSL::SSL::SSLError => e
  puts "✗ Still failed: #{e.message}"
end

# Test 3: Check what certs are available
puts "\n--- Checking certificate store ---"
puts "Files in cert dir:"
if File.directory?(OpenSSL::X509::DEFAULT_CERT_DIR)
  Dir.glob("#{OpenSSL::X509::DEFAULT_CERT_DIR}/*").first(10).each do |f|
    puts "  #{f}"
  end
else
  puts "  Directory doesn't exist!"
end

if File.exist?(OpenSSL::X509::DEFAULT_CERT_FILE)
  puts "\nCert file exists: #{OpenSSL::X509::DEFAULT_CERT_FILE}"
  puts "Size: #{File.size(OpenSSL::X509::DEFAULT_CERT_FILE)} bytes"
else
  puts "\n✗ Cert file doesn't exist: #{OpenSSL::X509::DEFAULT_CERT_FILE}"
end