diff --git a/Gemfile b/Gemfile
index a4415ab8..f14eb3b1 100644
--- a/Gemfile
+++ b/Gemfile
@@ -18,7 +18,7 @@ gem 'kramdown', '~> 1.2', require: false
 gem 'slim', '>= 2.0', require: false
 gem 'liquid', '>= 2.6', require: false
 gem 'stylus', '>= 1.0', require: false
-gem 'sinatra', '>= 2.0.0.beta2', require: false
+gem 'sinatra', '>= 1.4', require: false
 gem 'redcarpet', '>= 3.1', require: false
 
 # Dns server to test preview server
diff --git a/middleman-core/middleman-core.gemspec b/middleman-core/middleman-core.gemspec
index 38df7be7..44626407 100644
--- a/middleman-core/middleman-core.gemspec
+++ b/middleman-core/middleman-core.gemspec
@@ -20,7 +20,7 @@ Gem::Specification.new do |s|
 
   # Core
   s.add_dependency('bundler', ['~> 1.1'])
-  s.add_dependency('rack', ['>= 1.4.5', '< 3'])
+  s.add_dependency('rack', ['>= 1.4.5', '< 2.0'])
   s.add_dependency('tilt', ['~> 2.0'])
   s.add_dependency('erubis')
   s.add_dependency('fast_blank')