diff --git a/.ruby-version b/.ruby-version
index 743af5e..6a81b4c 100644
--- a/.ruby-version
+++ b/.ruby-version
@@ -1 +1 @@
-2.6.8
+2.7.8
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 670014b..aa74570 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -12,11 +12,14 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ### Changed
 - Switch `colorize` gem for `rainbow`
+- Upgrade project to Ruby 2.7.8
 
 ### Deprecated
 
 ### Removed
 - Removed `bpdocs.yml`
+- Removed support for Ruby 2.6.x
+- Removed debugging dependencies
 
 ### Fixed
 - Fix documentation formatting for MKDocs
diff --git a/Gemfile b/Gemfile
index 7f4f5e9..f2ca1dd 100644
--- a/Gemfile
+++ b/Gemfile
@@ -3,3 +3,15 @@
 source 'https://rubygems.org'
 
 gemspec
+
+gem 'generator_spec', '~> 0.9'
+gem 'guard', '~> 2.17'
+gem 'guard-rspec', '~> 4.7'
+gem 'guard-rubocop', '~> 1.5'
+gem 'rake', '~> 13.0'
+gem 'rspec', '~> 3.10'
+gem 'rubocop', '~> 1.21'
+gem 'rubocop-performance', '~> 1.11'
+gem 'rubocop-rake', '~> 0.5'
+gem 'rubocop-rspec', '~> 2.5'
+gem 'sqlite3', '~> 1.3.13'
diff --git a/onesie.gemspec b/onesie.gemspec
index c723d72..d19d4be 100644
--- a/onesie.gemspec
+++ b/onesie.gemspec
@@ -10,7 +10,7 @@ Gem::Specification.new do |spec|
   spec.summary       = 'Onesie Task Runner'
   spec.description   = ''
   spec.homepage      = 'https://github.com/timlkelly/onesie'
-  spec.required_ruby_version = Gem::Requirement.new('>= 2.6.3')
+  spec.required_ruby_version = Gem::Requirement.new('>= 2.7')
 
   spec.metadata['changelog_uri']         = 'https://github.com/timlkelly/onesie/blob/main/CHANGELOG.md'
   spec.metadata['github_repo']           = 'ssh://github.com/timlkelly/onesie'
@@ -28,20 +28,6 @@ Gem::Specification.new do |spec|
   spec.executables   = spec.files.grep(%r{\Aexe/}) { |f| File.basename(f) }
   spec.require_paths = ['lib']
 
-  spec.add_development_dependency 'generator_spec',      '~> 0.9'
-  spec.add_development_dependency 'guard',               '~> 2.17'
-  spec.add_development_dependency 'guard-rspec',         '~> 4.7'
-  spec.add_development_dependency 'guard-rubocop',       '~> 1.5'
-  spec.add_development_dependency 'pry',                 '~> 0.14'
-  spec.add_development_dependency 'pry-stack_explorer',  '~> 0.6'
-  spec.add_development_dependency 'rake',                '~> 13.0'
-  spec.add_development_dependency 'rspec',               '~> 3.10'
-  spec.add_development_dependency 'rubocop',             '~> 1.21'
-  spec.add_development_dependency 'rubocop-performance', '~> 1.11'
-  spec.add_development_dependency 'rubocop-rake',        '~> 0.5'
-  spec.add_development_dependency 'rubocop-rspec',       '~> 2.5'
-  spec.add_development_dependency 'sqlite3',             '~> 1.3.13'
-
   spec.add_runtime_dependency 'activerecord', '>= 4.2.11.3', '<= 5.2.8.1'
   spec.add_runtime_dependency 'railties',     '>= 4.2.11.3', '<= 5.2.8.1'
   spec.add_runtime_dependency 'rainbow',      '~> 3'
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index 8e7dea9..7acebf7 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -1,8 +1,5 @@
 # frozen_string_literal: true
 
-require 'pry'
-require 'pry-stack_explorer'
-
 require 'onesie'
 require 'support/active_record'
 require 'support/rspec'