diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 847c7381..4c58cd5e 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -11,29 +11,30 @@ permissions:
 
 jobs:
   test:
+    name: ${{ matrix.ruby }} (Rack ${{ matrix.rack }}, Puma ${{ matrix.puma }})
     permissions:
       contents: read #  to fetch code (actions/checkout)
       actions: read #  to list jobs for workflow run (8398a7/action-slack)
-
-    name: ${{ matrix.ruby }} (Rack ${{ matrix.rack }}, Puma ${{ matrix.puma }})
     runs-on: ubuntu-latest
     timeout-minutes: 15
     strategy:
       fail-fast: false
       matrix:
         puma:
-          - '~> 5' # Due to https://github.com/puma/puma/issues/3000
-        rack:
           - stable
+        rack:
+          - '~> 2'
         # Due to https://github.com/actions/runner/issues/849, we have to use quotes for '3.0'
         ruby: [2.6, 2.7, '3.0', 3.1, 'jruby-9.3', truffleruby, truffleruby-head]
         include:
-          - { ruby: 3.1, rack: stable, puma: latest, allow-failure: true }
-          - { ruby: 3.1, rack: latest, allow-failure: true }
-          - { ruby: jruby-head, rack: stable, allow-failure: true }
+          - { ruby: 3.1, rack: stable, puma: stable, gemfile: gems/rack-v3.rb, allow-failure: true }
+          - { ruby: 3.1, rack: latest, puma: latest, gemfile: gems/rack-v3.rb, allow-failure: true }
+          - { ruby: jruby-head, rack: stable, puma: stable, gemfile: gems/rack-v3.rb, allow-failure: true }
     env:
       rack: ${{ matrix.rack }}
       puma: ${{ matrix.puma }}
+      BUNDLE_GEMFILE: ${{ matrix.gemfile }}
+
     steps:
     - name: Install dependencies
       run: |
diff --git a/Gemfile b/Gemfile
index 6884186d..4868e11a 100644
--- a/Gemfile
+++ b/Gemfile
@@ -24,7 +24,6 @@ puma_version = { github: 'puma/puma' } if puma_version == 'latest'
 gem 'puma', puma_version
 
 gem 'minitest', '~> 5.0'
-gem 'rack-test', github: 'rack/rack-test'
 gem 'rubocop', '~> 1.32.0', require: false
 gem 'yard'
 
diff --git a/gems/rack-v3.rb b/gems/rack-v3.rb
new file mode 100644
index 00000000..0650c0c4
--- /dev/null
+++ b/gems/rack-v3.rb
@@ -0,0 +1,4 @@
+eval_gemfile("../Gemfile")
+
+gem "rackup"
+gem "rack-session"
diff --git a/rack-protection/Gemfile b/rack-protection/Gemfile
index cc444308..520dee07 100644
--- a/rack-protection/Gemfile
+++ b/rack-protection/Gemfile
@@ -13,5 +13,3 @@ gem 'rack', rack_version
 gem 'sinatra', path: '..'
 
 gemspec
-
-gem 'rack-test', github: 'rack/rack-test'
diff --git a/sinatra-contrib/Gemfile b/sinatra-contrib/Gemfile
index f0ae875c..6e26b939 100644
--- a/sinatra-contrib/Gemfile
+++ b/sinatra-contrib/Gemfile
@@ -6,8 +6,6 @@ gemspec
 gem 'rack-protection', path: '../rack-protection'
 gem 'sinatra', path: '..'
 
-gem 'rack-test', github: 'rack/rack-test'
-
 group :development, :test do
   platform :jruby do
     gem 'json'
@@ -38,6 +36,6 @@ repos = { 'tilt' => 'rtomayko/tilt', 'rack' => 'rack/rack' }
 %w[tilt rack].each do |lib|
   dep = (ENV[lib] || 'stable').sub "#{lib}-", ''
   dep = nil if dep == 'stable'
-  dep = { github: repos[lib], branch: dep } if dep && dep !~ (/(\d+\.)+\d+/)
+  dep = { github: repos[lib], branch: dep } if dep && dep !~ (/(\d+\.?)+(\d+)?/)
   gem lib, dep if dep
 end
diff --git a/sinatra.gemspec b/sinatra.gemspec
index 8f9cf599..c74d4e78 100644
--- a/sinatra.gemspec
+++ b/sinatra.gemspec
@@ -46,7 +46,7 @@ RubyGems 2.0 or newer is required to protect against public gem pushes. You can
   s.required_ruby_version = '>= 2.6.0'
 
   s.add_dependency 'mustermann', '~> 3.0'
-  s.add_dependency 'rack', '~> 2.2', '>= 2.2.4'
+  s.add_dependency 'rack', '>= 2.2.4', '< 4'
   s.add_dependency 'rack-protection', version
   s.add_dependency 'tilt', '~> 2.0'
 
diff --git a/test/server_test.rb b/test/server_test.rb
index efacddb1..c4ae62f7 100644
--- a/test/server_test.rb
+++ b/test/server_test.rb
@@ -24,7 +24,7 @@ module Rack::Handler
     end
   end
 
-  register 'mock', 'Rack::Handler::Mock'
+  register :mock, Mock
 end
 
 class ServerTest < Minitest::Test