Update with latest_major condition and ensure gem presence

.gitlab-ci.yml

@@ -206,6 +206,7 @@ prepare_image_destinations:
     - when: manual
       allow_failure: true
   script:
+    - ./.gitlab/check_gem_presence.rb $CI_COMMIT_TAG
     - echo "IMG_DESTINATIONS=$(./.gitlab/prepare_image_destinations.rb dd-lib-ruby-init $CI_COMMIT_TAG)" >> build.env
   artifacts:
     reports:

.gitlab/check_gem_presence.rb

@@ -0,0 +1,37 @@
+#!/usr/bin/env ruby
+
+require 'bundler/inline'
+
+gemfile { gem 'gems', source: 'https://rubygems.org' }
+
+require 'rubygems'
+require 'gems'
+
+version = ARGV[0].chomp
+version = version.delete_prefix('v') if version.start_with?('v')
+
+candidate = Gem::Version.new(version)
+
+retry_count = 0
+max_retries = 60
+interval = 60
+
+loop do
+  versions = Gems.versions('datadog').map { |h| Gem::Version.new(h['number']) }
+
+  if versions.include?(candidate)
+    puts "Gem version #{candidate} found!"
+    exit 0
+  else
+    retry_count += 1
+    puts "Attempt(#{retry_count}):  Gem 'ddtrace' version '#{candidate}' not found."
+
+    if retry_count >= max_retries
+      puts "Max retries(#{max_retries}) reached, stopping..."
+      exit 1
+    else
+      puts "Retrying in #{interval} seconds..."
+      sleep interval
+    end
+  end
+end

.gitlab/prepare_image_destinations.rb

@@ -12,27 +12,31 @@
 version = version.delete_prefix('v') if version.start_with?('v')
 
 candidate = Gem::Version.new(version)
+versions = Gems.versions('datadog').map { |h| Gem::Version.new(h['number']) }
 
+# Make sure candidate has already been published to 'https://rubygems.org'
+unless versions.include?(candidate)
+  warn "Version #{candidate} not found in RubyGems"
+  exit 1
+end
+
+# Skip pre-releases
 if candidate.prerelease?
   warn 'No tags for pre-releases'
   exit 1
 end
 
 major, minor, = candidate.to_s.split('.')
-
-latest_major_tag = "v#{major}"          # contains major
-latest_minor_tag = "v#{major}.#{minor}" # contains major, minor
+current_major_versions = versions.select { |v| v.to_s.start_with?("#{major}.") }
 
 tags = []
 
-gem_name = 'datadog'
-
-# Check if the candidate is larger than public latest version
-tags << 'latest' if candidate > Gem::Version.new(Gems.latest_version(gem_name).fetch('version'))
-tags << latest_major_tag
-tags << latest_minor_tag
+tags << 'latest'    if versions.all? { |v| candidate >= v }
+tags << "v#{major}" if current_major_versions.all? { |v| candidate >= v }
+tags << "v#{major}.#{minor}"
 tags << "v#{candidate}"
 
-destinations = tags.map { |tag| "#{image_name}:#{tag}" }
+# $stdout.puts "tags: #{tags}" # Uncomment for debugging
 
+destinations = tags.map { |tag| "#{image_name}:#{tag}" }
 $stdout.puts destinations.join(',')