upgrade_gems.rb

#!/env/bin ruby

require "fileutils"

def process(dir)

  puts "Analyzing #{dir}"
  FileUtils.cd(dir)

  puts "Finding outdated gems"
  output = `bundle outdated --strict --only-explicit --parseable`

  output.each_line do |line|
    next if line.blank?

    gem_name, newest_version, installed_version = parse_outdated_line(line)
    next if gem_name.nil?

    puts "Updating gem #{gem_name} to #{newest_version} from #{installed_version}"
    upgrade_gem(gem_name)
  end
end

def upgrade_gem(gem_name)
  `git checkout master`
  `git checkout -b update-gem-#{gem_name}`
  `bundle update #{gem_name}`
  `git add Gemfile.lock`
  `git commit -m 'Update gem #{gem_name}'`
  `git push`
  `hub pull-request -m 'Update gem #{gem_name}'`
end

def parse_outdated_line(line)
  /(.+) \(newest (.+), installed (.+)\)/.match(line)&.captures
end

process("/Users/gshaw/Sites/chitchats")

Would there be value in adding the gem version in the PR desc / commit message?