diff --git a/.ruby-version b/.ruby-version
index 2c9b4ef4..15a27998 100644
--- a/.ruby-version
+++ b/.ruby-version
@@ -1 +1 @@
-2.7.3
+3.3.0
diff --git a/Dockerfile b/Dockerfile
index 7fca990c..2c315ce8 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,4 +1,4 @@
-FROM ruby:2.7
+FROM ruby:3.3
 
 ENV GLOBAL_GEMS=true
 
diff --git a/Gemfile b/Gemfile
index 05161448..ba26298c 100644
--- a/Gemfile
+++ b/Gemfile
@@ -6,11 +6,11 @@ gem 'kramdown'
 # jekyll depends on kramdown-parser-gfm, but fails to declare it
 gem 'kramdown-parser-gfm'
 # Pin to the version used on GitHub Pages
-gem 'jekyll', 3.9
+gem 'jekyll', '~> 3'
 gem 'jekyll-redirect-from'
 
 # For testing output
-gem 'html-proofer'
+gem 'html-proofer', '~> 4'
 
 # Avoid polling on windows
 gem 'wdm', '>= 0.1.0'
diff --git a/Gemfile.lock b/Gemfile.lock
index 030b2f6a..5b916926 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -1,19 +1,20 @@
 GEM
   remote: https://rubygems.org/
   specs:
-    addressable (2.8.1)
-      public_suffix (>= 2.0.2, < 6.0)
+    addressable (2.8.7)
+      public_suffix (>= 2.0.2, < 7.0)
     colorator (1.1.0)
-    concurrent-ruby (1.1.8)
-    em-websocket (0.5.2)
+    concurrent-ruby (1.3.4)
+    csv (3.3.0)
+    em-websocket (0.5.3)
       eventmachine (>= 0.12.9)
-      http_parser.rb (~> 0.6.0)
-    ethon (0.15.0)
+      http_parser.rb (~> 0)
+    ethon (0.16.0)
       ffi (>= 1.15.0)
     eventmachine (1.2.7)
     eventmachine (1.2.7-x64-mingw32)
-    ffi (1.15.5)
-    ffi (1.15.5-x64-mingw32)
+    ffi (1.17.0)
+    ffi (1.17.0-x64-mingw32)
     forwardable-extended (2.6.0)
     html-proofer (4.4.3)
       addressable (~> 2.3)
@@ -24,14 +25,15 @@ GEM
       typhoeus (~> 1.3)
       yell (~> 2.0)
       zeitwerk (~> 2.5)
-    http_parser.rb (0.6.0)
-    i18n (0.9.5)
+    http_parser.rb (0.8.0)
+    i18n (1.14.5)
       concurrent-ruby (~> 1.0)
-    jekyll (3.9.0)
+    jekyll (3.10.0)
       addressable (~> 2.4)
       colorator (~> 1.0)
+      csv (~> 3.0)
       em-websocket (~> 0.5)
-      i18n (~> 0.7)
+      i18n (>= 0.7, < 2)
       jekyll-sass-converter (~> 1.0)
       jekyll-watch (~> 2.0)
       kramdown (>= 1.17, < 3)
@@ -40,43 +42,43 @@ GEM
       pathutil (~> 0.9)
       rouge (>= 1.7, < 4)
       safe_yaml (~> 1.0)
+      webrick (>= 1.0)
     jekyll-redirect-from (0.16.0)
       jekyll (>= 3.3, < 5.0)
     jekyll-sass-converter (1.5.2)
       sass (~> 3.4)
     jekyll-watch (2.2.1)
       listen (~> 3.0)
-    kramdown (2.3.1)
+    kramdown (2.4.0)
       rexml
     kramdown-parser-gfm (1.1.0)
       kramdown (~> 2.0)
-    liquid (4.0.3)
-    listen (3.7.1)
+    liquid (4.0.4)
+    listen (3.9.0)
       rb-fsevent (~> 0.10, >= 0.10.3)
       rb-inotify (~> 0.9, >= 0.9.10)
     mercenary (0.3.6)
-    mini_portile2 (2.8.5)
-    neat (3.0.0)
-      sass (~> 3.4)
+    mini_portile2 (2.8.7)
+    neat (4.0.0)
       thor (~> 0.19)
     nokogiri (1.15.6)
       mini_portile2 (~> 2.8.2)
       racc (~> 1.4)
     nokogiri (1.15.6-x64-mingw32)
       racc (~> 1.4)
-    parallel (1.22.1)
+    parallel (1.26.3)
     pathutil (0.16.2)
       forwardable-extended (~> 2.6)
-    public_suffix (5.0.0)
-    racc (1.7.3)
+    public_suffix (5.1.1)
+    racc (1.8.1)
     rainbow (3.1.1)
-    rake (12.3.3)
-    rb-fsevent (0.11.0)
-    rb-inotify (0.10.1)
+    rake (13.2.1)
+    rb-fsevent (0.11.2)
+    rb-inotify (0.11.1)
       ffi (~> 1.0)
-    rexml (3.3.3)
+    rexml (3.3.5)
       strscan
-    rouge (3.26.0)
+    rouge (3.30.0)
     safe_yaml (1.0.5)
     sass (3.7.4)
       sass-listen (~> 4.0.0)
@@ -85,20 +87,20 @@ GEM
       rb-inotify (~> 0.9, >= 0.9.7)
     strscan (3.1.0)
     thor (0.20.3)
-    typhoeus (1.4.0)
+    typhoeus (1.4.1)
       ethon (>= 0.9.0)
-    wdm (0.1.1)
-    webrick (1.7.0)
+    wdm (0.2.0)
+    webrick (1.8.1)
     yell (2.2.2)
-    zeitwerk (2.6.1)
+    zeitwerk (2.6.17)
 
 PLATFORMS
   ruby
   x64-mingw32
 
 DEPENDENCIES
-  html-proofer
-  jekyll (= 3.9)
+  html-proofer (~> 4)
+  jekyll (~> 3)
   jekyll-redirect-from
   kramdown
   kramdown-parser-gfm
@@ -108,4 +110,4 @@ DEPENDENCIES
   webrick (~> 1.7)
 
 BUNDLED WITH
-   2.1.4
+   2.3.6
diff --git a/README.md b/README.md
index d9014fe7..2e3daa02 100644
--- a/README.md
+++ b/README.md
@@ -14,7 +14,7 @@ Once setup, the site will be accessible on http://localhost:4000/docs/
 
 1. [Install Ruby][install-ruby]
 
-2. Install Bundler (2.x) and Rake
+2. Install Bundler (2.3 or above) and Rake
 
     ``` shell
     $ gem install bundler rake
diff --git a/Rakefile b/Rakefile
index 5f58afea..337d3ebd 100644
--- a/Rakefile
+++ b/Rakefile
@@ -1,3 +1,4 @@
+require 'date'
 require 'fileutils'
 require 'set'
 require 'yaml'
@@ -44,7 +45,7 @@ end
 task :build_spellings => [:build, :spelling_dependencies]
 
 task :validate_kit_versions do
-  data = YAML.load_file('_data/kit_versions.yml')
+  data = YAML.load_file('_data/kit_versions.yml', permitted_classes: [Date])
   data.each do |entry|
     actual = entry.keys.to_set
     expected = ['version', 'released', 'link', 'changelog'].to_set