diff --git a/.github/ISSUE_TEMPLATE/bug-report.yml b/.github/ISSUE_TEMPLATE/bug-report.yml
index ce758c51734..d91c69064b3 100644
--- a/.github/ISSUE_TEMPLATE/bug-report.yml
+++ b/.github/ISSUE_TEMPLATE/bug-report.yml
@@ -35,7 +35,7 @@ body:
   - type: input
     attributes:
       label: Language version
-      description: If applicable, specify the language version you're using (e.g., Node.js `14.1`, Ruby `2.7`, etc.)
+      description: If applicable, specify the language version you're using (e.g., Node.js `14.1`, Ruby `3.1`, etc.)
     validations:
       required: false
 
diff --git a/.rubocop.yml b/.rubocop.yml
index 1d5710b4aa2..763aa81b251 100644
--- a/.rubocop.yml
+++ b/.rubocop.yml
@@ -256,6 +256,8 @@ Style/HashExcept:
   Enabled: true
 Style/HashLikeCase:
   Enabled: false
+Style/HashSyntax:
+  EnforcedShorthandSyntax: either
 Style/HashTransformKeys:
   Enabled: false
 Style/HashTransformValues:
@@ -320,3 +322,13 @@ Style/SpecialGlobalVars:
   Enabled: false
 Style/SelectByRegexp:
   Enabled: false
+
+# TODO these were temporarily disabled during the Ruby 2.7 -> 3.1 upgrade
+# in order to keep the upgrade diff small, they will be enabled/fixed in
+# a follow-on PR.
+Naming/BlockForwarding:
+  Enabled: false
+Style/MutableConstant:
+  Enabled: false
+Style/RedundantFreeze:
+  Enabled: false
diff --git a/.ruby-version b/.ruby-version
index 49cdd668e1c..ef538c28109 100644
--- a/.ruby-version
+++ b/.ruby-version
@@ -1 +1 @@
-2.7.6
+3.1.2
diff --git a/Dockerfile b/Dockerfile
index b68c489feb3..1130ad7f049 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -68,7 +68,7 @@ RUN if ! getent group "$USER_GID"; then groupadd --gid "$USER_GID" dependabot ;
 
 ### RUBY
 
-ARG RUBY_VERSION=2.7.6
+ARG RUBY_VERSION=3.1.2
 ARG RUBY_INSTALL_VERSION=0.8.3
 
 ARG RUBYGEMS_SYSTEM_VERSION=3.3.22
diff --git a/common/dependabot-common.gemspec b/common/dependabot-common.gemspec
index 764900dcea9..254637b59a7 100644
--- a/common/dependabot-common.gemspec
+++ b/common/dependabot-common.gemspec
@@ -18,7 +18,7 @@ Gem::Specification.new do |spec|
   spec.require_path = "lib"
   spec.files        = []
 
-  spec.required_ruby_version = ">= 2.7.0"
+  spec.required_ruby_version = ">= 3.1.0"
   spec.required_rubygems_version = ">= 3.3.22"
 
   spec.add_dependency "activesupport", ">= 6.0.0"
@@ -35,8 +35,6 @@ Gem::Specification.new do |spec|
   spec.add_dependency "parser", ">= 2.5", "< 4.0"
   spec.add_dependency "toml-rb", ">= 1.1.2", "< 3.0"
 
-  spec.add_development_dependency "debase", "0.2.3"
-  spec.add_development_dependency "debase-ruby_core_source", "0.10.17"
   spec.add_development_dependency "debug", ">= 1.0.0"
   spec.add_development_dependency "gpgme", "~> 2.0"
   spec.add_development_dependency "parallel_tests", "~> 3.13.0"
@@ -45,7 +43,6 @@ Gem::Specification.new do |spec|
   spec.add_development_dependency "rspec-its", "~> 1.2"
   spec.add_development_dependency "rubocop", "~> 1.36.0"
   spec.add_development_dependency "rubocop-performance", "~> 1.15.0"
-  spec.add_development_dependency "ruby-debug-ide", "~> 0.7.3"
   spec.add_development_dependency "simplecov", "~> 0.21.0"
   spec.add_development_dependency "simplecov-console", "~> 0.9.1"
   spec.add_development_dependency "stackprof", "~> 0.2.16"
diff --git a/common/spec/warning_monkey_patch.rb b/common/spec/warning_monkey_patch.rb
index 10af502fef7..399c85568d4 100644
--- a/common/spec/warning_monkey_patch.rb
+++ b/common/spec/warning_monkey_patch.rb
@@ -1,11 +1,11 @@
 # frozen_string_literal: true
 
 ALLOW_PATTERNS = [
-  # Ignore parser warnings for ruby 2.7 minor version mismatches.
+  # Ignore `parser/current` warnings for ruby patch version mismatches.
   # This is a recurring issue that occurs whenever the parser gets
   # ahead of our installed ruby version.
-  %r{parser/current is loading parser/ruby27},
-  /2.7.\d-compliant syntax, but you are running 2.7.\d/,
+  %r{parser/current is loading parser/ruby31},
+  /3.1.\d-compliant syntax, but you are running 3.1.\d/,
   %r{whitequark/parser}
 ].freeze
 
diff --git a/omnibus/dependabot-omnibus.gemspec b/omnibus/dependabot-omnibus.gemspec
index 4e8ff643f54..23e4487c9cc 100644
--- a/omnibus/dependabot-omnibus.gemspec
+++ b/omnibus/dependabot-omnibus.gemspec
@@ -17,7 +17,7 @@ Gem::Specification.new do |spec|
   spec.homepage     = common_gemspec.homepage
   spec.license      = common_gemspec.license
 
-  spec.required_ruby_version = ">= 2.7.0"
+  spec.required_ruby_version = ">= 3.1.0"
   spec.require_path = "lib"
   spec.files        = ["lib/dependabot/omnibus.rb"]
 
diff --git a/pub/dependabot-pub.gemspec b/pub/dependabot-pub.gemspec
index ad7b92ecdca..50bb68e3815 100644
--- a/pub/dependabot-pub.gemspec
+++ b/pub/dependabot-pub.gemspec
@@ -24,6 +24,8 @@ Gem::Specification.new do |spec|
 
   spec.add_dependency "dependabot-common", Dependabot::VERSION
 
+  spec.add_development_dependency "webrick", ">= 1.7"
+
   common_gemspec.development_dependencies.each do |dep|
     spec.add_development_dependency dep.name, dep.requirement.to_s
   end
diff --git a/updater/Gemfile b/updater/Gemfile
index d084ae33af3..e0e7c37262d 100644
--- a/updater/Gemfile
+++ b/updater/Gemfile
@@ -27,7 +27,7 @@ gem "sentry-raven", "~> 3.1"
 gem "terminal-table", "~> 3.0.2"
 
 group :test do
-  gem "byebug", "~> 11.1"
+  gem "debug", "~> 1.0.0"
   gem "rspec", "~> 3.11"
   gem "rubocop", "~> 1.36.0"
   gem "rubocop-performance", "~> 1.15.0"
diff --git a/updater/spec/spec_helper.rb b/updater/spec/spec_helper.rb
index 5fe57eb7ef7..e7c2efa6597 100644
--- a/updater/spec/spec_helper.rb
+++ b/updater/spec/spec_helper.rb
@@ -1,6 +1,5 @@
 # frozen_string_literal: true
 
-require "byebug"
 require "dependabot/logger"
 require "dependabot/python"
 require "dependabot/terraform"