diff --git a/changelog/new_add_document_dynamic_eval_definition_cop.md b/changelog/new_add_document_dynamic_eval_definition_cop.md
new file mode 100644
index 00000000000..3f839991295
--- /dev/null
+++ b/changelog/new_add_document_dynamic_eval_definition_cop.md
@@ -0,0 +1 @@
+* [#8940](https://github.com/rubocop-hq/rubocop/pull/8940): Add new `Style/DocumentDynamicEvalDefinition` cop. ([@fatkodima][])
diff --git a/config/default.yml b/config/default.yml
index e137d8fe264..04e88c1a1a3 100644
--- a/config/default.yml
+++ b/config/default.yml
@@ -2946,6 +2946,14 @@ Style/DisableCopsWithinSourceCodeDirective:
   Enabled: false
   VersionAdded: '0.82'
 
+Style/DocumentDynamicEvalDefinition:
+  Description: >-
+                When using `class_eval` (or other `eval`) with string interpolation,
+                add a comment block showing its appearance if interpolated.
+  StyleGuide: '#eval-comment-docs'
+  Enabled: pending
+  VersionAdded: '1.1'
+
 Style/Documentation:
   Description: 'Document classes and non-namespace modules.'
   Enabled: true
diff --git a/docs/modules/ROOT/pages/cops.adoc b/docs/modules/ROOT/pages/cops.adoc
index b36cc370fd6..df4e69e0729 100644
--- a/docs/modules/ROOT/pages/cops.adoc
+++ b/docs/modules/ROOT/pages/cops.adoc
@@ -374,6 +374,7 @@ In the following section you find all available cops:
 * xref:cops_style.adoc#styledefwithparentheses[Style/DefWithParentheses]
 * xref:cops_style.adoc#styledir[Style/Dir]
 * xref:cops_style.adoc#styledisablecopswithinsourcecodedirective[Style/DisableCopsWithinSourceCodeDirective]
+* xref:cops_style.adoc#styledocumentdynamicevaldefinition[Style/DocumentDynamicEvalDefinition]
 * xref:cops_style.adoc#styledocumentation[Style/Documentation]
 * xref:cops_style.adoc#styledocumentationmethod[Style/DocumentationMethod]
 * xref:cops_style.adoc#styledoublecopdisabledirective[Style/DoubleCopDisableDirective]
diff --git a/docs/modules/ROOT/pages/cops_style.adoc b/docs/modules/ROOT/pages/cops_style.adoc
index b3752a7e447..a5de9fd3e37 100644
--- a/docs/modules/ROOT/pages/cops_style.adoc
+++ b/docs/modules/ROOT/pages/cops_style.adoc
@@ -2195,6 +2195,64 @@ def fixed_method_name_and_no_rubocop_comments
 end
 ----
 
+== Style/DocumentDynamicEvalDefinition
+
+|===
+| Enabled by default | Safe | Supports autocorrection | VersionAdded | VersionChanged
+
+| Pending
+| Yes
+| No
+| 1.1
+| -
+|===
+
+When using `class_eval` (or other `eval`) with string interpolation,
+add a comment block showing its appearance if interpolated (a practice used in Rails code).
+
+=== Examples
+
+[source,ruby]
+----
+# from activesupport/lib/active_support/core_ext/string/output_safety.rb
+
+# bad
+UNSAFE_STRING_METHODS.each do |unsafe_method|
+  if 'String'.respond_to?(unsafe_method)
+    class_eval <<-EOT, __FILE__, __LINE__ + 1
+      def #{unsafe_method}(*params, &block)
+        to_str.#{unsafe_method}(*params, &block)
+      end
+
+      def #{unsafe_method}!(*params)
+        @dirty = true
+        super
+      end
+    EOT
+  end
+end
+
+# good
+UNSAFE_STRING_METHODS.each do |unsafe_method|
+  if 'String'.respond_to?(unsafe_method)
+    class_eval <<-EOT, __FILE__, __LINE__ + 1
+      def #{unsafe_method}(*params, &block)       # def capitalize(*params, &block)
+        to_str.#{unsafe_method}(*params, &block)  #   to_str.capitalize(*params, &block)
+      end                                         # end
+
+      def #{unsafe_method}!(*params)              # def capitalize!(*params)
+        @dirty = true                             #   @dirty = true
+        super                                     #   super
+      end                                         # end
+    EOT
+  end
+end
+----
+
+=== References
+
+* https://rubystyle.guide#eval-comment-docs
+
 == Style/Documentation
 
 |===
diff --git a/lib/rubocop.rb b/lib/rubocop.rb
index bb3569ca409..daddae89079 100644
--- a/lib/rubocop.rb
+++ b/lib/rubocop.rb
@@ -424,6 +424,7 @@
 require_relative 'rubocop/cop/style/disable_cops_within_source_code_directive'
 require_relative 'rubocop/cop/style/documentation_method'
 require_relative 'rubocop/cop/style/documentation'
+require_relative 'rubocop/cop/style/document_dynamic_eval_definition'
 require_relative 'rubocop/cop/style/double_cop_disable_directive'
 require_relative 'rubocop/cop/style/double_negation'
 require_relative 'rubocop/cop/style/each_for_simple_loop'
diff --git a/lib/rubocop/cop/commissioner.rb b/lib/rubocop/cop/commissioner.rb
index 98e00fb6ef9..7f3aa25a931 100644
--- a/lib/rubocop/cop/commissioner.rb
+++ b/lib/rubocop/cop/commissioner.rb
@@ -65,13 +65,13 @@ def initialize(cops, forces = [], options = {})
         c = '#' if NO_CHILD_NODES.include?(node_type) # has Children?
 
         class_eval(<<~RUBY, __FILE__, __LINE__ + 1)
-                  def on_#{node_type}(node)
-                    trigger_responding_cops(:on_#{node_type}, node)
-              #{r}  trigger_restricted_cops(:on_#{node_type}, node)
-          #{c}      super(node)
-          #{c}      trigger_responding_cops(:after_#{node_type}, node)
-          #{c}#{r}  trigger_restricted_cops(:after_#{node_type}, node)
-                  end
+                  def on_#{node_type}(node)                               # def on_send(node)
+                    trigger_responding_cops(:on_#{node_type}, node)       #   trigger_responding_cops(:on_send, node)
+              #{r}  trigger_restricted_cops(:on_#{node_type}, node)       #   trigger_restricted_cops(:on_send, node)
+          #{c}      super(node)                                           #   super(node)
+          #{c}      trigger_responding_cops(:after_#{node_type}, node)    #   trigger_responding_cops(:after_send, node)
+          #{c}#{r}  trigger_restricted_cops(:after_#{node_type}, node)    #   trigger_restricted_cops(:after_send, node)
+                  end                                                     # end
         RUBY
       end
 
diff --git a/lib/rubocop/cop/style/document_dynamic_eval_definition.rb b/lib/rubocop/cop/style/document_dynamic_eval_definition.rb
new file mode 100644
index 00000000000..5ed39c0b5ea
--- /dev/null
+++ b/lib/rubocop/cop/style/document_dynamic_eval_definition.rb
@@ -0,0 +1,67 @@
+# frozen_string_literal: true
+
+module RuboCop
+  module Cop
+    module Style
+      # When using `class_eval` (or other `eval`) with string interpolation,
+      # add a comment block showing its appearance if interpolated (a practice used in Rails code).
+      #
+      # @example
+      #   # from activesupport/lib/active_support/core_ext/string/output_safety.rb
+      #
+      #   # bad
+      #   UNSAFE_STRING_METHODS.each do |unsafe_method|
+      #     if 'String'.respond_to?(unsafe_method)
+      #       class_eval <<-EOT, __FILE__, __LINE__ + 1
+      #         def #{unsafe_method}(*params, &block)
+      #           to_str.#{unsafe_method}(*params, &block)
+      #         end
+      #
+      #         def #{unsafe_method}!(*params)
+      #           @dirty = true
+      #           super
+      #         end
+      #       EOT
+      #     end
+      #   end
+      #
+      #   # good
+      #   UNSAFE_STRING_METHODS.each do |unsafe_method|
+      #     if 'String'.respond_to?(unsafe_method)
+      #       class_eval <<-EOT, __FILE__, __LINE__ + 1
+      #         def #{unsafe_method}(*params, &block)       # def capitalize(*params, &block)
+      #           to_str.#{unsafe_method}(*params, &block)  #   to_str.capitalize(*params, &block)
+      #         end                                         # end
+      #
+      #         def #{unsafe_method}!(*params)              # def capitalize!(*params)
+      #           @dirty = true                             #   @dirty = true
+      #           super                                     #   super
+      #         end                                         # end
+      #       EOT
+      #     end
+      #   end
+      #
+      class DocumentDynamicEvalDefinition < Base
+        MSG = 'Add a comment block showing its appearance if interpolated.'
+
+        RESTRICT_ON_SEND = %i[eval class_eval module_eval instance_eval].freeze
+
+        def on_send(node)
+          arg_node = node.first_argument
+          return unless arg_node&.dstr_type?
+
+          add_offense(node.loc.selector) unless comment_docs?(arg_node)
+        end
+
+        private
+
+        def comment_docs?(node)
+          node.each_child_node(:begin).all? do |begin_node|
+            source_line = processed_source.lines[begin_node.first_line - 1]
+            source_line.match?(/\s*#[^{]+/)
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/spec/rubocop/cop/style/document_dynamic_eval_definition_spec.rb b/spec/rubocop/cop/style/document_dynamic_eval_definition_spec.rb
new file mode 100644
index 00000000000..7de41586637
--- /dev/null
+++ b/spec/rubocop/cop/style/document_dynamic_eval_definition_spec.rb
@@ -0,0 +1,36 @@
+# frozen_string_literal: true
+
+RSpec.describe RuboCop::Cop::Style::DocumentDynamicEvalDefinition do
+  subject(:cop) { described_class.new }
+
+  it 'registers an offense when using eval-type method with string interpolation without comment docs' do
+    expect_offense(<<~RUBY)
+      class_eval <<-EOT, __FILE__, __LINE__ + 1
+      ^^^^^^^^^^ Add a comment block showing its appearance if interpolated.
+        def \#{unsafe_method}(*params, &block)
+          to_str.\#{unsafe_method}(*params, &block)
+        end
+      EOT
+    RUBY
+  end
+
+  it 'does not register an offense when using eval-type method without string interpolation' do
+    expect_no_offenses(<<~RUBY)
+      class_eval <<-EOT, __FILE__, __LINE__ + 1
+        def capitalize(*params, &block)
+          to_str.capitalize(*params, &block)
+        end
+      EOT
+    RUBY
+  end
+
+  it 'does not register an offense when using eval-type method with string interpolation with comment docs' do
+    expect_no_offenses(<<~RUBY)
+      class_eval <<-EOT, __FILE__, __LINE__ + 1
+        def \#{unsafe_method}(*params, &block)       # def capitalize(*params, &block)
+          to_str.\#{unsafe_method}(*params, &block)  #   to_str.capitalize(*params, &block)
+        end                                          # end
+      EOT
+    RUBY
+  end
+end