diff --git a/Gemfile b/Gemfile
index 2b5766896d6..23e6e342383 100644
--- a/Gemfile
+++ b/Gemfile
@@ -17,17 +17,18 @@ end
 
 gem "cheffish", "~> 17.0.0"
 
+gem "ast", "~> 2.4.2"
+gem "rubocop-ast", ">= 1.30.0"
+
 group(:omnibus_package) do
   gem "appbundler"
   gem "rb-readline"
-  gem "inspec-core-bin", ">= 4.24" # need to provide the binaries for inspec
+  gem "inspec-core-bin", "~> 5.22.36" # need to provide the binaries for inspec
   gem "chef-vault"
 end
 
 group(:omnibus_package, :pry) do
-  # Locked because pry-byebug is broken with 13+.
-  # some work is ongoing? https://github.com/deivid-rodriguez/pry-byebug/issues/343
-  gem "pry", "= 0.13.0"
+  gem "pry", ">= 0.14.1"
   # byebug does not install on freebsd on ruby 3.0
   gem "pry-byebug" unless RUBY_PLATFORM.match?(/freebsd/i)
   gem "pry-stack_explorer"
diff --git a/Gemfile.lock b/Gemfile.lock
index 80c2d95300d..fb65c4befb1 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -1,9 +1,9 @@
 GIT
   remote: https://github.com/chef/chefstyle.git
-  revision: 71ae97744713ffd91ac8277d7a1385dabb6d570b
+  revision: 129344227d927ea67f228540654a6718265d03cd
   branch: main
   specs:
-    chefstyle (2.2.2)
+    chefstyle (2.2.3)
       rubocop (= 1.25.1)
 
 GIT
@@ -50,7 +50,7 @@ PATH
       ffi-libarchive (~> 1.0, >= 1.0.3)
       ffi-yajl (~> 2.2)
       iniparse (~> 1.4)
-      inspec-core (>= 4.23)
+      inspec-core (~> 5.22.36)
       license-acceptance (>= 1.0.5, < 3)
       mixlib-archive (>= 0.4, < 2.0)
       mixlib-authentication (>= 2.1, < 4)
@@ -82,7 +82,7 @@ PATH
       ffi-libarchive (~> 1.0, >= 1.0.3)
       ffi-yajl (~> 2.2)
       iniparse (~> 1.4)
-      inspec-core (>= 4.23)
+      inspec-core (~> 5.22.36)
       iso8601 (>= 0.12.1, < 0.14)
       license-acceptance (>= 1.0.5, < 3)
       mixlib-archive (>= 0.4, < 2.0)
@@ -221,31 +221,31 @@ GEM
     hashie (4.1.0)
     httpclient (2.8.3)
     iniparse (1.5.0)
-    inspec-core (5.22.3)
+    inspec-core (5.22.36)
       addressable (~> 2.4)
       chef-telemetry (~> 1.0, >= 1.0.8)
       faraday (>= 1, < 3)
       faraday-follow_redirects (~> 0.3)
-      hashie (>= 3.4, < 5.0)
+      hashie (>= 3.4, < 6.0)
       license-acceptance (>= 0.2.13, < 3.0)
       method_source (>= 0.8, < 2.0)
       mixlib-log (~> 3.0)
       multipart-post (~> 2.0)
       parallel (~> 1.9)
-      parslet (>= 1.5, < 2.0)
+      parslet (>= 1.5, < 3.0)
       pry (~> 0.13)
-      rspec (>= 3.9, <= 3.11)
+      rspec (>= 3.9, <= 3.12)
       rspec-its (~> 1.2)
       rubyzip (>= 1.2.2, < 3.0)
       semverse (~> 3.0)
       sslshake (~> 1.2)
-      thor (>= 0.20, < 2.0)
+      thor (>= 0.20, < 1.3.0)
       tomlrb (>= 1.2, < 2.1)
       train-core (~> 3.10)
       tty-prompt (~> 0.17)
       tty-table (~> 0.10)
-    inspec-core-bin (5.22.3)
-      inspec-core (= 5.22.3)
+    inspec-core-bin (5.22.36)
+      inspec-core (= 5.22.36)
     ipaddress (0.8.3)
     iso8601 (0.13.0)
     jmespath (1.6.2)
@@ -294,7 +294,7 @@ GEM
       tty-color (~> 0.5)
     plist (3.7.0)
     proxifier (1.0.3)
-    pry (0.13.0)
+    pry (0.14.2)
       coderay (~> 1.1)
       method_source (~> 1.0)
     pry-byebug (3.10.1)
@@ -307,7 +307,7 @@ GEM
     racc (1.7.1)
     rack (2.2.7)
     rainbow (3.1.1)
-    rake (13.0.6)
+    rake (13.1.0)
     rb-readline (0.5.5)
     regexp_parser (2.8.1)
     rexml (3.2.5)
@@ -336,7 +336,7 @@ GEM
       rubocop-ast (>= 1.15.1, < 2.0)
       ruby-progressbar (~> 1.7)
       unicode-display_width (>= 1.4.0, < 3.0)
-    rubocop-ast (1.29.0)
+    rubocop-ast (1.30.0)
       parser (>= 3.2.1.0)
     ruby-progressbar (1.13.0)
     ruby2_keywords (0.0.5)
@@ -442,6 +442,7 @@ PLATFORMS
 
 DEPENDENCIES
   appbundler
+  ast (~> 2.4.2)
   chef!
   chef-bin!
   chef-config!
@@ -451,14 +452,15 @@ DEPENDENCIES
   chefstyle!
   ed25519 (~> 1.2)
   fauxhai-ng
-  inspec-core-bin (>= 4.24)
+  inspec-core-bin (~> 5.22.36)
   ohai!
-  pry (= 0.13.0)
+  pry (>= 0.14.1)
   pry-byebug
   pry-stack_explorer
   rake
   rb-readline
   rspec
+  rubocop-ast (>= 1.30.0)
   ruby-shadow!
   webmock
 
diff --git a/chef.gemspec b/chef.gemspec
index ae3c90a01b9..c13722eecde 100644
--- a/chef.gemspec
+++ b/chef.gemspec
@@ -36,7 +36,7 @@ Gem::Specification.new do |s|
   s.add_dependency "mixlib-shellout", ">= 3.1.1", "< 4.0"
   s.add_dependency "mixlib-archive", ">= 0.4", "< 2.0"
   s.add_dependency "ohai", "~> 17.0"
-  s.add_dependency "inspec-core", ">= 4.23"
+  s.add_dependency "inspec-core", "~> 5.22.36"
 
   s.add_dependency "ffi", "~> 1.15.0"
   s.add_dependency "ffi-yajl", "~> 2.2"