Maybe a rescue?

rescue.rb

thr = Thread.new do
  started = false
  finished = false
  
  def cleanup
    puts '...started cleaning resource' unless started
    started = true
    sleep 1
    puts '...finished cleaning resource' unless finished
    finished = true
  rescue Timeout::Error
    cleanup # just try again
  end
  
  begin
    puts '...initializing resource'
    sleep 1

    raise 'something went wrong'

    puts '...using resource'
    sleep 1
  ensure
    cleanup
  end
end