diff --git a/.travis.yml b/.travis.yml
index 26f2ee2..9d91816 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -14,6 +14,9 @@ matrix:
       script: gem build github_changelog_generator && bundle install
       gemfile: spec/install-gem-in-bundler.gemfile
     - rvm: 2.1
+      gemfile: gemfiles/Gemfile.with_rack16
+    - rvm: 2.3.1
+      gemfile: gemfiles/Gemfile.with_rack2
 
 notifications:
   email:
diff --git a/Gemfile b/Gemfile
index e4177cb..9ff95e2 100644
--- a/Gemfile
+++ b/Gemfile
@@ -2,9 +2,6 @@ source "https://rubygems.org"
 
 gemspec
 
-group :development do
-end
-
 group :development, :test do
   gem "rake"
   gem "bundler"
@@ -13,8 +10,6 @@ group :development, :test do
 end
 
 group :test do
-  gem 'rack', '< 2' # In tests, we use this
-
   gem "coveralls", "~>0.8", require: false
   gem "simplecov", "~>0.10", require: false
   gem "codeclimate-test-reporter", "~>0.4"
diff --git a/Gemfile.lock b/Gemfile.lock
index b77628b..3c6158a 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -2,8 +2,8 @@ PATH
   remote: .
   specs:
     github_changelog_generator (1.13.1)
+      github_api (>= 0.14)
       rainbow (>= 2.1)
-      github_api (>= 0.12)
       rake (>= 10.0)
 
 GEM
@@ -28,32 +28,32 @@ GEM
     faraday (0.9.2)
       multipart-post (>= 1.2, < 3)
     ffi (1.9.14)
-    github_api (0.14.4)
+    github_api (0.14.5)
       addressable (~> 2.4.0)
       descendants_tracker (~> 0.0.4)
       faraday (~> 0.8, < 0.10)
       hashie (>= 3.4)
-      oauth2 (~> 1.0.0)
-    hashie (3.4.4)
+      oauth2 (~> 1.0)
+    hashie (3.4.6)
     iniparse (1.4.2)
     json (1.8.3)
-    jwt (1.5.4)
+    jwt (1.5.6)
     multi_json (1.12.1)
     multi_xml (0.5.5)
     multipart-post (2.0.0)
-    oauth2 (1.0.0)
+    oauth2 (1.2.0)
       faraday (>= 0.8, < 0.10)
       jwt (~> 1.0)
       multi_json (~> 1.3)
       multi_xml (~> 0.5)
-      rack (~> 1.2)
+      rack (>= 1.2, < 3)
     overcommit (0.34.2)
       childprocess (~> 0.5.8)
       iniparse (~> 1.4)
-    parser (2.3.1.2)
+    parser (2.3.1.4)
       ast (~> 2.2)
     powerpack (0.1.1)
-    rack (1.6.4)
+    rack (2.0.1)
     rainbow (2.1.0)
     rake (11.2.2)
     rspec (3.5.0)
@@ -69,7 +69,7 @@ GEM
       diff-lcs (>= 1.2.0, < 2.0)
       rspec-support (~> 3.5.0)
     rspec-support (3.5.0)
-    rubocop (0.41.2)
+    rubocop (0.43.0)
       parser (>= 2.3.1.1, < 3.0)
       powerpack (~> 0.1)
       rainbow (>= 1.99.1, < 3.0)
@@ -86,7 +86,7 @@ GEM
     thor (0.19.1)
     thread_safe (0.3.5)
     tins (1.6.0)
-    unicode-display_width (1.1.0)
+    unicode-display_width (1.1.1)
 
 PLATFORMS
   ruby
@@ -96,12 +96,12 @@ DEPENDENCIES
   codeclimate-test-reporter (~> 0.4)
   coveralls (~> 0.8)
   github_changelog_generator!
-  json (< 2.0)
-  overcommit
+  json
+  overcommit (>= 0.31)
   rake
-  rspec (>= 3.2)
-  rubocop
+  rspec (< 4)
+  rubocop (>= 0.43)
   simplecov (~> 0.10)
 
 BUNDLED WITH
-   1.12.5
+   1.13.1
diff --git a/gemfiles/Gemfile.with_rack16 b/gemfiles/Gemfile.with_rack16
new file mode 100644
index 0000000..e32cd73
--- /dev/null
+++ b/gemfiles/Gemfile.with_rack16
@@ -0,0 +1,2 @@
+eval_gemfile File.expand_path('../../Gemfile', __FILE__)
+gem 'rack', '~> 1.6'
diff --git a/gemfiles/Gemfile.with_rack2 b/gemfiles/Gemfile.with_rack2
new file mode 100644
index 0000000..22ec100
--- /dev/null
+++ b/gemfiles/Gemfile.with_rack2
@@ -0,0 +1,2 @@
+eval_gemfile File.expand_path('../../Gemfile', __FILE__)
+gem 'rack', '>= 2'