diff --git a/lib/buildsystems/ruby.rb b/lib/buildsystems/ruby.rb
index 91ac552c8..7c3da735f 100644
--- a/lib/buildsystems/ruby.rb
+++ b/lib/buildsystems/ruby.rb
@@ -91,8 +91,9 @@ class RUBY < Package
     if installed_gem_search
       installed_gem_info = installed_gem_search.delete('()').gsub('default:', '').gsub(',', '').split
       @gem_installed_version = installed_gem_info[1]
-      @gem_outdated = (Gem::Version.new(@gem_version) < Gem::Version.new(@gem_installed_version))
+      @gem_outdated = (Gem::Version.new(@gem_version) > Gem::Version.new(@gem_installed_version))
       @gem_latest_version_installed = Gem::Version.new(@gem_version) <= Gem::Version.new(@gem_installed_version)
+      crewlog "@gem_version: #{@gem_version} @gem_installed_version: #{@gem_installed_version} @gem_outdated: #{@gem_outdated} @gem_latest_version_installed: #{@gem_latest_version_installed}"
     end
 
     # Create a filelist from the gem if the latest gem version is
@@ -134,8 +135,9 @@ class RUBY < Package
     if installed_gem_search
       installed_gem_info = installed_gem_search.delete('()').gsub('default:', '').gsub(',', '').split
       @gem_installed_version = installed_gem_info[1]
-      @gem_outdated = (Gem::Version.new(@gem_version) < Gem::Version.new(@gem_installed_version))
+      @gem_outdated = (Gem::Version.new(@gem_version) > Gem::Version.new(@gem_installed_version))
       @gem_latest_version_installed = Gem::Version.new(@gem_version) <= Gem::Version.new(@gem_installed_version)
+      crewlog "@gem_version: #{@gem_version} @gem_installed_version: #{@gem_installed_version} @gem_outdated: #{@gem_outdated} @gem_latest_version_installed: #{@gem_latest_version_installed}"
     end
 
     crewlog "no_compile_needed?: #{no_compile_needed?} @gem_binary_build_needed.blank?: #{@gem_binary_build_needed.blank?}, gem_compile_needed?: #{gem_compile_needed?}"
diff --git a/lib/const.rb b/lib/const.rb
index 269331319..3fa6809d0 100644
--- a/lib/const.rb
+++ b/lib/const.rb
@@ -3,7 +3,7 @@
 require 'etc'
 
 OLD_CREW_VERSION ||= defined?(CREW_VERSION) ? CREW_VERSION : '1.0'
-CREW_VERSION ||= '1.55.2' unless defined?(CREW_VERSION) && CREW_VERSION == OLD_CREW_VERSION
+CREW_VERSION ||= '1.55.3' unless defined?(CREW_VERSION) && CREW_VERSION == OLD_CREW_VERSION
 
 # Kernel architecture.
 KERN_ARCH ||= Etc.uname[:machine]