diff --git a/features/incremental_rebuild.feature b/features/incremental_rebuild.feature
index 2d22d2e1..8eacaf23 100644
--- a/features/incremental_rebuild.feature
+++ b/features/incremental_rebuild.feature
@@ -67,6 +67,59 @@ Feature: Incremental rebuild
     And the _site directory should exist
     And I should see "Basic Site with include tag: Regenerated by Jekyll" in "_site/index.html"
 
+  Scenario: Rebuild when a data file is changed
+    Given I have a _data directory
+    And I have a "_data/colors.yml" file that contains "[red, green, blue]"
+    And I have a _data/members/core directory
+    And I have a "_data/members/core/emeritus.yml" file with content:
+      """
+      - name: John Doe
+        role: Admin
+      """
+    And I have an _includes directory
+    And I have an "_includes/about.html" file with content:
+      """
+      <ul>
+      {% for entry in site.data.members.core.emeritus %}
+        <li title="{{ entry.name }} -- {{ entry.role }}">{{ entry.name }}</li>
+      {% endfor %}
+      </ul>
+      """
+    And I have a _layouts directory
+    And I have a page layout that contains "{{ content }}\n\n{% include about.html %}"
+    And I have a home layout that contains "{{ content }}\n\nGenerated by Jekyll"
+    And I have a "_layouts/post.html" page with layout "page" that contains "{{ content }}"
+    And I have a "_layouts/static.html" page with layout "home" that contains "{{ content }}"
+    And I have an "index.html" page with layout "home" that contains "{{ site.data.colors | join: '_' }}"
+    And I have an "about.html" page with layout "page" that contains "About Us"
+    And I have a configuration file with "collections_dir" set to "collections"
+    And I have a collections/_posts directory
+    And I have the following post within the "collections" directory:
+      | title    | date       | layout  | content                      |
+      | Table    | 2009-03-26 | post    | Post with data dependency    |
+      | Wargames | 2009-03-27 | static  | Post without data dependency |
+    When I run jekyll build -IV
+    Then I should get a zero exit status
+    And the _site directory should exist
+    And I should see "red_green_blue" in "_site/index.html"
+    And I should see "John Doe -- Admin" in "_site/about.html"
+    And I should see "Rendering: index.html" in the build output
+    And I should see "Rendering: _posts/2009-03-27-wargames.markdown" in the build output
+    When I wait 1 second
+    Then I have a "_data/members/core/emeritus.yml" file with content:
+      """
+      - name: Jane Doe
+        role: Admin
+      """
+    When I run jekyll build -IV
+    Then I should get a zero exit status
+    And the _site directory should exist
+    And I should see "red_green_blue" in "_site/index.html"
+    And I should see "Jane Doe -- Admin" in "_site/about.html"
+    And I should see "Rendering: _posts/2009-03-26-table.markdown" in the build output
+    But I should not see "Rendering: index.html" in the build output
+    And I should not see "Rendering: _posts/2009-03-27-wargames.markdown" in the build output
+
   Scenario: Rebuild when a dependency of document in custom collection_dir is changed
     Given I have a _includes directory
     And I have a configuration file with "collections_dir" set to "collections"
diff --git a/lib/jekyll.rb b/lib/jekyll.rb
index 231f8fd8..49b71e70 100644
--- a/lib/jekyll.rb
+++ b/lib/jekyll.rb
@@ -45,6 +45,8 @@ module Jekyll
   autoload :Collection,          "jekyll/collection"
   autoload :Configuration,       "jekyll/configuration"
   autoload :Convertible,         "jekyll/convertible"
+  autoload :DataEntry,           "jekyll/data_entry"
+  autoload :DataHash,            "jekyll/data_hash"
   autoload :Deprecator,          "jekyll/deprecator"
   autoload :Document,            "jekyll/document"
   autoload :EntryFilter,         "jekyll/entry_filter"
diff --git a/lib/jekyll/data_entry.rb b/lib/jekyll/data_entry.rb
new file mode 100644
index 00000000..fa267221
--- /dev/null
+++ b/lib/jekyll/data_entry.rb
@@ -0,0 +1,83 @@
+# frozen_string_literal: true
+
+module Jekyll
+  class DataEntry
+    attr_accessor :context
+    attr_reader :data
+
+    # Create a Jekyll wrapper for given parsed data object.
+    #
+    #        site - The current Jekyll::Site instance.
+    #    abs_path - Absolute path to the data source file.
+    # parsed_data - Parsed representation of data source file contents.
+    #
+    # Returns nothing.
+    def initialize(site, abs_path, parsed_data)
+      @site = site
+      @path = abs_path
+      @data = parsed_data
+    end
+
+    # Liquid representation of current instance is the parsed data object.
+    #
+    # Mark as a dependency for regeneration here since every renderable object primarily uses the
+    # parsed data object while the parent resource is being rendered by Liquid. Accessing the data
+    # object directly via Ruby interface `#[]()` is outside the scope of regeneration.
+    #
+    # FIXME: Marking as dependency on every call is non-ideal. Optimize at later day.
+    #
+    # Returns the parsed data object.
+    def to_liquid
+      add_regenerator_dependencies if incremental_build?
+      @data
+    end
+
+    # -- Overrides to maintain backwards compatibility --
+
+    # Any missing method will be forwarded to the underlying data object stored in the instance
+    # variable `@data`.
+    def method_missing(method, *args, &block)
+      @data.respond_to?(method) ? @data.send(method, *args, &block) : super
+    end
+
+    def respond_to_missing?(method, *)
+      @data.respond_to?(method) || super
+    end
+
+    def <=>(other)
+      data <=> (other.is_a?(self.class) ? other.data : other)
+    end
+
+    def ==(other)
+      data == (other.is_a?(self.class) ? other.data : other)
+    end
+
+    # Explicitly defined to bypass re-routing from `method_missing` hook for greater performance.
+    #
+    # Returns string representation of parsed data object.
+    def inspect
+      @data.inspect
+    end
+
+    private
+
+    def incremental_build?
+      @incremental = @site.config["incremental"] if @incremental.nil?
+      @incremental
+    end
+
+    def add_regenerator_dependencies
+      page = context.registers[:page]
+      return unless page&.key?("path")
+
+      absolute_path = \
+        if page["collection"]
+          @site.in_source_dir(@site.config["collections_dir"], page["path"])
+        else
+          @site.in_source_dir(page["path"])
+        end
+
+      @site.regenerator.add_dependency(absolute_path, @path)
+    end
+  end
+end
diff --git a/lib/jekyll/data_hash.rb b/lib/jekyll/data_hash.rb
new file mode 100644
index 00000000..37ef510b
--- /dev/null
+++ b/lib/jekyll/data_hash.rb
@@ -0,0 +1,61 @@
+# frozen_string_literal: true
+
+module Jekyll
+  # A class that behaves very similar to Ruby's `Hash` class yet different in how it is handled by
+  # Liquid. This class emulates Hash by delegation instead of inheritance to minimize overridden
+  # methods especially since some Hash methods returns another Hash instance instead of the
+  # subclass instance.
+  class DataHash
+    #
+    # Delegate given (zero-arity) method(s) to the Hash object stored in instance variable
+    # `@registry`.
+    # NOTE: Avoiding the use of `Forwardable` module's `def_delegators` for preventing unnecessary
+    # creation of interim objects on multiple calls.
+    def self.delegate_to_registry(*symbols)
+      symbols.each { |sym| define_method(sym) { @registry.send(sym) } }
+    end
+    private_class_method :delegate_to_registry
+
+    # -- core instance methods --
+
+    attr_accessor :context
+
+    def initialize
+      @registry = {}
+    end
+
+    def [](key)
+      @registry[key].tap do |value|
+        value.context = context if value.respond_to?(:context=)
+      end
+    end
+
+    # `Hash#to_liquid` returns the Hash instance itself.
+    # Mimic that behavior by returning `self` instead of returning the `@registry` variable value.
+    def to_liquid
+      self
+    end
+
+    # -- supplementary instance methods to emulate Hash --
+
+    delegate_to_registry :freeze, :inspect
+
+    def merge(other, &block)
+      merged_registry = @registry.merge(other, &block)
+      dup.tap { |d| d.instance_variable_set(:@registry, merged_registry) }
+    end
+
+    def merge!(other, &block)
+      @registry.merge!(other, &block)
+      self
+    end
+
+    def method_missing(method, *args, &block)
+      @registry.send(method, *args, &block)
+    end
+
+    def respond_to_missing?(method, *)
+      @registry.respond_to?(method)
+    end
+  end
+end
diff --git a/lib/jekyll/drops/site_drop.rb b/lib/jekyll/drops/site_drop.rb
index cc3c60fb..13c5757b 100644
--- a/lib/jekyll/drops/site_drop.rb
+++ b/lib/jekyll/drops/site_drop.rb
@@ -7,7 +7,6 @@ module Jekyll
 
       mutable false
 
-      delegate_method_as :site_data, :data
       delegate_methods :time, :pages, :static_files, :tags, :categories
 
       private delegate_method_as :config, :fallback_data
@@ -24,6 +23,12 @@ module Jekyll
         (key != "posts" && @obj.collections.key?(key)) || super
       end
 
+      def data
+        @obj.site_data.tap do |value|
+          value.context = @context if value.respond_to?(:context=)
+        end
+      end
+
       def posts
         @site_posts ||= @obj.posts.docs.sort { |a, b| b <=> a }
       end
diff --git a/lib/jekyll/readers/data_reader.rb b/lib/jekyll/readers/data_reader.rb
index 80b57bd6..f95556da 100644
--- a/lib/jekyll/readers/data_reader.rb
+++ b/lib/jekyll/readers/data_reader.rb
@@ -6,7 +6,7 @@ module Jekyll
 
     def initialize(site, in_source_dir: nil)
       @site = site
-      @content = {}
+      @content = DataHash.new
       @entry_filter = EntryFilter.new(site)
       @in_source_dir = in_source_dir || @site.method(:in_source_dir)
       @source_dir = @in_source_dir.call("/")
@@ -24,6 +24,8 @@ module Jekyll
       @content
     end
 
+    # rubocop:disable Metrics/AbcSize
+
     # Read and parse all .yaml, .yml, .json, .csv and .tsv
     # files under <dir> and add them to the <data> variable.
     #
@@ -43,13 +45,14 @@ module Jekyll
         next if @entry_filter.symlink?(path)
 
         if File.directory?(path)
-          read_data_to(path, data[sanitize_filename(entry)] = {})
+          read_data_to(path, data[sanitize_filename(entry)] = DataHash.new)
         else
           key = sanitize_filename(File.basename(entry, ".*"))
-          data[key] = read_data_file(path)
+          data[key] = DataEntry.new(site, path, read_data_file(path))
         end
       end
     end
+    # rubocop:enable Metrics/AbcSize
 
     # Determines how to read a data file.
     #
diff --git a/lib/jekyll/utils.rb b/lib/jekyll/utils.rb
index 2a965270..8eb807d7 100644
--- a/lib/jekyll/utils.rb
+++ b/lib/jekyll/utils.rb
@@ -47,7 +47,14 @@ module Jekyll
     end
 
     def mergable?(value)
-      value.is_a?(Hash) || value.is_a?(Drops::Drop)
+      case value
+      when Hash, Drops::Drop, DataHash
+        true
+      when DataEntry
+        mergable?(value.data)
+      else
+        false
+      end
     end
 
     def duplicable?(obj)
diff --git a/test/source/_data/boolean.yml b/test/source/_data/boolean.yml
new file mode 100644
index 00000000..fe75c80b
--- /dev/null
+++ b/test/source/_data/boolean.yml
@@ -0,0 +1 @@
+true
diff --git a/test/source/_data/languages_plus.yml b/test/source/_data/languages_plus.yml
new file mode 100644
index 00000000..fb98401b
--- /dev/null
+++ b/test/source/_data/languages_plus.yml
@@ -0,0 +1,4 @@
+- java
+- ruby
+- rust
+- golang
diff --git a/test/test_data_entry.rb b/test/test_data_entry.rb
new file mode 100644
index 00000000..dc6e8e93
--- /dev/null
+++ b/test/test_data_entry.rb
@@ -0,0 +1,34 @@
+# frozen_string_literal: true
+
+require "helper"
+
+class TestDataEntry < JekyllUnitTest
+  context "Data Entry" do
+    setup do
+      site = fixture_site
+      site.read
+      @data_hash = site.site_data
+    end
+
+    should "expose underlying data object es Liquid representation" do
+      subject = @data_hash["languages"]
+      assert_equal Jekyll::DataEntry, subject.class
+      assert_equal subject.data, subject.to_liquid
+    end
+
+    should "respond to `#[](key)` when expected to but raise Exception otherwise" do
+      greeting = @data_hash["greetings"]
+      assert greeting["foo"]
+
+      boolean = @data_hash["boolean"] # the value is a Boolean.
+      assert_raises(NoMethodError) { boolean["foo"] }
+    end
+
+    should "compare with another instance of same class using underlying data" do
+      assert_equal(
+        [%w(java ruby), %w(java ruby rust golang)],
+        [@data_hash["languages_plus"], @data_hash["languages"]].sort
+      )
+    end
+  end
+end
diff --git a/test/test_data_hash.rb b/test/test_data_hash.rb
new file mode 100644
index 00000000..022c2543
--- /dev/null
+++ b/test/test_data_hash.rb
@@ -0,0 +1,57 @@
+# frozen_string_literal: true
+
+require "helper"
+
+class TestDataHash < JekyllUnitTest
+  context "Data Hash" do
+    setup do
+      @site = fixture_site
+      @site.read
+    end
+
+    should "only mimic a ::Hash instance" do
+      subject = @site.site_data
+      assert_equal Jekyll::DataHash, subject.class
+      refute subject.is_a?(Hash)
+
+      copy = subject.dup
+      assert copy["greetings"]["foo"]
+      assert_includes copy.dig("greetings", "foo"), "Hello!"
+
+      copy["greetings"] = "Hola!"
+      assert_equal "Hola!", copy["greetings"]
+      refute copy["greetings"]["foo"]
+
+      frozen_data_hash = Jekyll::DataHash.new.freeze
+      assert_raises(FrozenError) { frozen_data_hash["lorem"] = "ipsum" }
+    end
+
+    should "be mergable" do
+      alpha = Jekyll::DataHash.new
+      beta  = Jekyll::DataHash.new
+
+      assert_equal "{}", alpha.inspect
+      sample_data = { "foo" => "bar" }
+
+      assert_equal sample_data["foo"], alpha.merge(sample_data)["foo"]
+      assert_equal alpha.class, alpha.merge(sample_data).class
+      assert_empty alpha
+
+      beta.merge!(sample_data)
+      assert_equal sample_data["foo"], alpha.merge(beta)["foo"]
+      assert_equal alpha.class, alpha.merge(beta).class
+      assert_empty alpha
+
+      beta.merge!(@site.site_data)
+      assert_equal alpha.class, beta.class
+      assert_includes beta.dig("greetings", "foo"), "Hello!"
+
+      assert_empty alpha
+      assert_equal sample_data["foo"], Jekyll::Utils.deep_merge_hashes(alpha, sample_data)["foo"]
+      assert_includes(
+        Jekyll::Utils.deep_merge_hashes(alpha, beta).dig("greetings", "foo"),
+        "Hello!"
+      )
+    end
+  end
+end