diff --git a/.github/workflows/ruby.yml b/.github/workflows/ruby.yml
index b6b6e26e..5bd8d281 100644
--- a/.github/workflows/ruby.yml
+++ b/.github/workflows/ruby.yml
@@ -14,7 +14,7 @@ jobs:
       matrix:
         ruby-version: ['3.0', '3.1', '3.2']
         activesupport-version: ['5', '6']
-        sinatra-version: ['1', '2']
+        sinatra-version: ['2', '3']
     env:
       ACTIVESUPPORT_MAJOR: ${{ matrix.activesupport-version }}
       SINATRA_MAJOR: ${{ matrix.sinatra-version }}
diff --git a/pliny.gemspec b/pliny.gemspec
index 4f0e348c..4c33b2a0 100644
--- a/pliny.gemspec
+++ b/pliny.gemspec
@@ -20,7 +20,7 @@ Gem::Specification.new do |gem|
   gem.add_dependency "prmd",           "~> 0.11", ">= 0.11.4"
 
 
-  gem.add_dependency "sinatra",        ">= 1.4", "< 3.0"
+  gem.add_dependency "sinatra",        ">= 2.0", "< 4.0"
   gem.add_dependency "http_accept",    "~> 0.1",  ">= 0.1.5"
   gem.add_dependency "sinatra-router", "~> 0.2",  ">= 0.2.4"
   gem.add_dependency "thor",           ">= 0.19", "< 2.0"
@@ -28,7 +28,7 @@ Gem::Specification.new do |gem|
   gem.add_development_dependency "rake",              "~> 13.0"
   gem.add_development_dependency "rack-test",         "~> 1.1.0"
   gem.add_development_dependency "rspec",             "~> 3.1", ">= 3.1.0"
-  gem.add_development_dependency "sinatra-contrib",   ">= 1.4", "< 3.0"
+  gem.add_development_dependency "sinatra-contrib",   ">= 2.0", "< 4.0"
   gem.add_development_dependency "timecop", "~> 0.7", ">= 0.7.1"
   gem.add_development_dependency "pry"
   gem.add_development_dependency "pry-byebug"