There are some inconvenient Gem dependencies. Resolve them by adding/modifying these lines in your Gemfile:

  gem 'guard-livereload', '>= 2.5.2', require: false # Fixes a security issue
  gem 'listen', '< 3.1' # 3.1 requires Ruby 2.2.5

Rails Long Term Support

Rails LTS provides security patches for old versions of Ruby on Rails (2.3, 3.2, 4.2 and 5.2)

• Prevents you from data breaches and liability risks
• Upgrade at your own pace
• Works with modern Rubies

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It is not possible to install guard-livereload 2.5.2 on Ruby 1.8.7 because it depends on guard 2.8, which requires Ruby 1.9.