diff --git a/.ruby-version b/.ruby-version
index a04abec91494..49cdd668e1c8 100644
--- a/.ruby-version
+++ b/.ruby-version
@@ -1 +1 @@
-2.6.10
+2.7.6
diff --git a/Dockerfile b/Dockerfile
index ac8204b96e97..2b2a676e5300 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -5,7 +5,7 @@
 
 # Use same ruby version as the one in .ruby-version
 # that is used by Netlify
-ARG RUBY_VERSION=2.6.10
+ARG RUBY_VERSION=2.7.6
 # Same as the one in Gemfile.lock
 ARG BUNDLER_VERSION=2.3.13
 
diff --git a/Gemfile b/Gemfile
index a17a5f85ec24..c48db4ffb412 100644
--- a/Gemfile
+++ b/Gemfile
@@ -3,15 +3,19 @@ source 'https://rubygems.org'
 gem 'tzinfo-data', platforms: [:mingw, :mswin, :x64_mingw, :jruby]
 gem 'wdm', '>= 0.1.0' if Gem.win_platform?
 
-gem 'jekyll', '3.8.6'
-gem 'jekyll-redirect-from'
-gem 'jekyll-relative-links'
-gem 'jekyll-sitemap'
+gem 'jekyll', '4.2.2'
+group :jekyll_plugins do
+  gem 'jekyll-redirect-from'
+  gem 'jekyll-relative-links'
+  gem 'jekyll-sitemap'
+end
 
-# FIXME: enforce rouge to old version for now: https://github.com/docker/docker.github.io/issues/14788
-gem 'rouge', "2.2.1"
+# FIXME: This is a workaround for a bug in rouge console lexer
+#  introduced by https://github.com/rouge-ruby/rouge/pull/1779
+#  more info: https://github.com/docker/docker.github.io/issues/14788
+gem 'rouge', '3.27.0'
 
-gem 'archive-zip'
-gem 'html-proofer'
-gem 'octopress-hooks'
-gem 'rake'
+gem 'archive-zip', '0.12.0'
+gem 'html-proofer', '3.19.4'
+gem 'octopress-hooks', '2.6.2'
+gem 'rake', '13.0.6'
diff --git a/Gemfile.lock b/Gemfile.lock
index b40c4b389333..93a4f19f442c 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -24,38 +24,49 @@ GEM
       typhoeus (~> 1.3)
       yell (~> 2.0)
     http_parser.rb (0.8.0)
-    i18n (0.9.5)
+    i18n (1.10.0)
       concurrent-ruby (~> 1.0)
     io-like (0.3.1)
-    jekyll (3.8.6)
+    jekyll (4.2.2)
       addressable (~> 2.4)
       colorator (~> 1.0)
       em-websocket (~> 0.5)
-      i18n (~> 0.7)
-      jekyll-sass-converter (~> 1.0)
+      i18n (~> 1.0)
+      jekyll-sass-converter (~> 2.0)
       jekyll-watch (~> 2.0)
-      kramdown (~> 1.14)
+      kramdown (~> 2.3)
+      kramdown-parser-gfm (~> 1.0)
       liquid (~> 4.0)
-      mercenary (~> 0.3.3)
+      mercenary (~> 0.4.0)
       pathutil (~> 0.9)
-      rouge (>= 1.7, < 4)
+      rouge (~> 3.0)
       safe_yaml (~> 1.0)
+      terminal-table (~> 2.0)
     jekyll-redirect-from (0.16.0)
       jekyll (>= 3.3, < 5.0)
     jekyll-relative-links (0.6.1)
       jekyll (>= 3.3, < 5.0)
-    jekyll-sass-converter (1.5.2)
-      sass (~> 3.4)
+    jekyll-sass-converter (2.2.0)
+      sassc (> 2.0.1, < 3.0)
     jekyll-sitemap (1.4.0)
       jekyll (>= 3.7, < 5.0)
     jekyll-watch (2.2.1)
       listen (~> 3.0)
-    kramdown (1.17.0)
+    kramdown (2.4.0)
+      rexml
+    kramdown-parser-gfm (1.1.0)
+      kramdown (~> 2.0)
     liquid (4.0.3)
     listen (3.7.1)
       rb-fsevent (~> 0.10, >= 0.10.3)
       rb-inotify (~> 0.9, >= 0.9.10)
-    mercenary (0.3.6)
+    mercenary (0.4.0)
+    mini_portile2 (2.8.0)
+    nokogiri (1.13.6)
+      mini_portile2 (~> 2.8.0)
+      racc (~> 1.4)
+    nokogiri (1.13.6-aarch64-linux)
+      racc (~> 1.4)
     nokogiri (1.13.6-x86_64-linux)
       racc (~> 1.4)
     octopress-hooks (2.6.2)
@@ -70,15 +81,16 @@ GEM
     rb-fsevent (0.11.1)
     rb-inotify (0.10.1)
       ffi (~> 1.0)
-    rouge (2.2.1)
+    rexml (3.2.5)
+    rouge (3.27.0)
     safe_yaml (1.0.5)
-    sass (3.7.4)
-      sass-listen (~> 4.0.0)
-    sass-listen (4.0.0)
-      rb-fsevent (~> 0.9, >= 0.9.4)
-      rb-inotify (~> 0.9, >= 0.9.7)
+    sassc (2.4.0)
+      ffi (~> 1.9)
+    terminal-table (2.0.0)
+      unicode-display_width (~> 1.1, >= 1.1.1)
     typhoeus (1.4.0)
       ethon (>= 0.9.0)
+    unicode-display_width (1.8.0)
     yell (2.2.2)
 
 PLATFORMS
@@ -87,15 +99,15 @@ PLATFORMS
   x86_64-linux
 
 DEPENDENCIES
-  archive-zip
-  html-proofer
-  jekyll (= 3.8.6)
+  archive-zip (= 0.12.0)
+  html-proofer (= 3.19.4)
+  jekyll (= 4.2.2)
   jekyll-redirect-from
   jekyll-relative-links
   jekyll-sitemap
-  octopress-hooks
-  rake
-  rouge (= 2.2.1)
+  octopress-hooks (= 2.6.2)
+  rake (= 13.0.6)
+  rouge (= 3.27.0)
   tzinfo-data
 
 BUNDLED WITH
diff --git a/_config.yml b/_config.yml
index 271cf04e30ec..a10b5bd3235b 100644
--- a/_config.yml
+++ b/_config.yml
@@ -3,19 +3,25 @@
 #
 # This file overrides options set in _config.yml for production / deploy
 ##
+
 name: Docker Documentation
+
 markdown: kramdown
+highlighter: rouge
+incremental: true
+permalink: pretty
+safe: false
+lsi: false
+
+# https://kramdown.gettalong.org/options.html
+# https://github.com/kramdown/parser-gfm/blob/master/lib/kramdown/parser/gfm/options.rb
 kramdown:
   input: GFM
   gfm_quirks: [paragraph_end, no_auto_typographic]
-  html_to_native: true
   hard_wrap: false
+  html_to_native: true
   syntax_highlighter: rouge
   toc_levels: 2..3
-incremental: true
-permalink: pretty
-safe: false
-lsi: false
 
 exclude:
   - _samples