diff --git a/packages/ruby/server/.rubocop.yml b/packages/ruby/server/.rubocop.yml
new file mode 100644
index 0000000..a4fea3e
--- /dev/null
+++ b/packages/ruby/server/.rubocop.yml
@@ -0,0 +1,40 @@
+##
+# Plugins
+require:
+  - standard
+
+##
+# Defaults: standard-rb
+inherit_gem:
+  standard: config/base.yml
+
+##
+# All cops
+AllCops:
+  TargetRubyVersion: 3.2
+  Include:
+    - lib/*.rb
+    - lib/**/*.rb
+    - test/*_test.rb
+
+##
+# Enabled
+Style/FrozenStringLiteralComment:
+  Enabled: true
+
+##
+# Disabled
+Layout/ArgumentAlignment:
+  Enabled: false
+Layout/MultilineMethodCallIndentation:
+  Enabled: false
+Layout/EmptyLineBetweenDefs:
+  Enabled: false
+Style/TrivialAccessors:
+  Enabled: false
+Lint/NestedMethodDefinition:
+  Exclude:
+    - test/server_dir_test.rb
+Style/SingleLineMethods:
+  Exclude:
+    - test/server_dir_test.rb
diff --git a/packages/ruby/server/lib/server.rb b/packages/ruby/server/lib/server.rb
index 543d35d..d97bd64 100644
--- a/packages/ruby/server/lib/server.rb
+++ b/packages/ruby/server/lib/server.rb
@@ -3,6 +3,7 @@
 class Server
   require "rack"
   require_relative "server/puma"
+  require_relative "server/gzip"
   require_relative "server/dir"
 
   def self.app(path)
diff --git a/packages/ruby/server/lib/server/dir.rb b/packages/ruby/server/lib/server/dir.rb
index d64ef48..cb1fe20 100644
--- a/packages/ruby/server/lib/server/dir.rb
+++ b/packages/ruby/server/lib/server/dir.rb
@@ -1,19 +1,17 @@
 # frozen_string_literal: true
 
+##
+# A rack application that serves the contents
+# of a directory over HTTP.
 class Server::Dir
-  MIME_TYPES = {
-    ".ttf" => "font/ttf"
-  }.freeze
+  prepend Server::Gzip
 
   def initialize(root)
     @root = File.realpath(root)
   end
 
   def call(env)
-    req = Rack::Request.new(env)
-    headers = Rack::Headers.new(env)
-    h, body = read(local_path(req.path))
-    [200, headers.merge!(h), body]
+    finish Rack::Request.new(env)
   rescue Errno::EPERM, Errno::EACCES
     body = "Permission denied"
     [403, {"content-length" => body.bytesize, "content-type" => "text/plain"}, [body]]
@@ -29,18 +27,24 @@ class Server::Dir
 
   attr_reader :root
 
-  def read(path)
+  def finish(request)
+    path = find_path(request)
     body = File.binread(path)
     extn = File.extname(path)
     [
-      {"content-type" => MIME_TYPES[extn] || Rack::Mime.mime_type(extn),
+      200,
+      {"content-type" => mime_types[extn] || Rack::Mime.mime_type(extn),
        "content-length" => body.bytesize},
       body.each_line
     ]
   end
 
-  def local_path(req_path)
-    lpath = File.join root, File.expand_path(req_path)
-    File.directory?(lpath) ? File.join(lpath, "index.html") : lpath
+  def find_path(request)
+    path = File.join root, File.expand_path(request.path)
+    File.directory?(path) ? File.join(path, "index.html") : path
+  end
+
+  def mime_types
+    {".ttf" => "font/ttf"}.freeze
   end
 end
diff --git a/packages/ruby/server/lib/server/gzip.rb b/packages/ruby/server/lib/server/gzip.rb
new file mode 100644
index 0000000..bfdeed2
--- /dev/null
+++ b/packages/ruby/server/lib/server/gzip.rb
@@ -0,0 +1,33 @@
+# frozen_string_literal: true
+
+##
+# A mixin module that serves a compressed version of
+# a file when the file is found to exist on disk,
+# and has a ".gz" file extension.
+module Server::Gzip
+  def finish(request)
+    path = gzip_path(request)
+    if path
+      body = File.binread(path)
+      extn = File.extname(path[0..-4])
+      [
+        200,
+        {"content-type" => mime_types[extn] || Rack::Mime.mime_type(extn),
+         "content-encoding" => "gzip",
+         "content-length" => body.bytesize},
+        body.each_line
+      ]
+    else
+      super
+    end
+  end
+
+  private
+
+  def gzip_path(request)
+    return unless request.get_header("accept-encoding")
+                        &.include?("gzip")
+    path = "#{find_path(request)}.gz"
+    File.exist?(path) ? path : nil
+  end
+end
diff --git a/packages/ruby/server/server.rb.gemspec b/packages/ruby/server/server.rb.gemspec
index 6f3d259..2b58bd6 100644
--- a/packages/ruby/server/server.rb.gemspec
+++ b/packages/ruby/server/server.rb.gemspec
@@ -10,6 +10,15 @@ Gem::Specification.new do |gem|
   gem.require_paths = ["lib"]
   gem.summary = "A static file web server"
   gem.description = gem.summary
+
+  ##
+  # Default gems
+  # Pinned to specific versions for OpenBSD support
+  gem.add_runtime_dependency "json", "= 2.6.1"
+  gem.add_runtime_dependency "racc", "= 1.6.0"
+  gem.add_runtime_dependency "stringio", "= 3.0.1"
+  gem.add_runtime_dependency "set", "= 1.0.2"
+
   gem.add_runtime_dependency "puma", "~> 6.3"
   gem.add_runtime_dependency "rack", "~> 3.0"
   gem.add_development_dependency "standard", "~> 1.24"
diff --git a/packages/ruby/server/test/server_dir_test.rb b/packages/ruby/server/test/server_dir_test.rb
index f09c799..c9de9a9 100644
--- a/packages/ruby/server/test/server_dir_test.rb
+++ b/packages/ruby/server/test/server_dir_test.rb
@@ -1,3 +1,5 @@
+# frozen_string_literal: true
+
 require_relative "setup"
 require "rack/test"
 
@@ -44,7 +46,7 @@ class ServerDirTest < Test::Unit::TestCase
   end
 
   def test_internal_server_error
-    def app.read(path) raise RuntimeError, "test" end
+    def app.finish(request) raise "test" end
     get "/"
     assert_equal 500, last_response.status
     assert_equal "text/plain", last_response.content_type
@@ -62,7 +64,7 @@ class ServerDirTest < Test::Unit::TestCase
     assert_equal "Permission denied".bytesize, last_response.content_length
     assert_equal "Permission denied", last_response.body
   ensure
-    File.chmod 0440, "./test/webroot/permission_denied.html"
+    File.chmod 0o440, "./test/webroot/permission_denied.html"
   end
 
   def test_page_not_found