diff --git a/Changelog.md b/Changelog.md
index c1b836fba..e1dd75f00 100644
--- a/Changelog.md
+++ b/Changelog.md
@@ -1,6 +1,10 @@
 ### Development
 [Full Changelog](http://github.com/rspec/rspec-expectations/compare/v3.12.0...main)
 
+Bug Fixes:
+
+* Fix keyword arguments delegation for `chain` in custom matchers. (Tyler Rick, #1374)
+
 ### 3.12.0 / 2022-10-26
 [Full Changelog](http://github.com/rspec/rspec-expectations/compare/v3.11.1...v3.12.0)
 
diff --git a/lib/rspec/matchers/dsl.rb b/lib/rspec/matchers/dsl.rb
index 9c6a48bf0..824309a57 100644
--- a/lib/rspec/matchers/dsl.rb
+++ b/lib/rspec/matchers/dsl.rb
@@ -306,6 +306,7 @@ def chain(method_name, *attr_names, &definition)
             @chained_method_clauses.push([method_name, args])
             self
           end
+          ruby2_keywords method_name if respond_to?(:ruby2_keywords, true)
         end
 
         def assign_attributes(attr_names)
diff --git a/spec/rspec/matchers/dsl_spec.rb b/spec/rspec/matchers/dsl_spec.rb
index c085cdce8..d4433cc14 100644
--- a/spec/rspec/matchers/dsl_spec.rb
+++ b/spec/rspec/matchers/dsl_spec.rb
@@ -354,8 +354,17 @@ def new_matcher(name, *expected, &block)
             (to_match <= five) || greater_than_ceiling(to_match) && not_divisible_by_divisor?(to_match)
           end
 
-          chain :and_smaller_than do |ceiling|
-            @ceiling = ceiling
+          if RSpec::Support::RubyFeatures.kw_args_supported?
+            binding.eval(<<-CODE, __FILE__, __LINE__)
+            chain :and_smaller_than do |ceiling, inclusive: false|
+              @ceiling = ceiling
+              @ceiling_inclusive = inclusive
+            end
+            CODE
+          else
+            chain :and_smaller_than do |ceiling|
+              @ceiling = ceiling
+            end
           end
 
           chain :and_divisible_by do |divisor|
@@ -364,8 +373,18 @@ def new_matcher(name, *expected, &block)
 
         private
 
-          def smaller_than_ceiling?(to_match)
-            to_match < @ceiling
+          if RSpec::Support::RubyFeatures.kw_args_supported?
+            def smaller_than_ceiling?(to_match)
+              if @ceiling_inclusive
+                to_match <= @ceiling
+              else
+                to_match < @ceiling
+              end
+            end
+          else
+            def smaller_than_ceiling?(to_match)
+              to_match < @ceiling
+            end
           end
 
           def greater_than_ceiling(to_match)
@@ -373,11 +392,11 @@ def greater_than_ceiling(to_match)
           end
 
           def divisible_by_divisor?(to_match)
-            @divisor % to_match == 0
+            to_match % @divisor == 0
           end
 
           def not_divisible_by_divisor?(to_match)
-            @divisor % to_match != 0
+            to_match % @divisor != 0
           end
         end
       end
@@ -397,7 +416,7 @@ def not_divisible_by_divisor?(to_match)
             expect { expect(8).to match }.to fail_with 'expected 8 to be bigger than 5'
           end
 
-          it "provides a default negative expectation failure message that does not include the any of the chained matchers's descriptions" do
+          it "provides a default negative expectation failure message that does not include any of the chained matchers' descriptions" do
             expect { expect(9).to_not match }.to fail_with 'expected 9 not to be bigger than 5'
           end
         end
@@ -421,6 +440,15 @@ def not_divisible_by_divisor?(to_match)
             expect { expect(21).to_not matcher.and_smaller_than(29).and_divisible_by(3) }.to \
               fail_with 'expected 21 not to be bigger than 5 and smaller than 29 and divisible by 3'
           end
+
+          if RSpec::Support::RubyFeatures.kw_args_supported?
+            binding.eval(<<-CODE, __FILE__, __LINE__)
+            it "allows passing keyword args to chain block" do
+              match = matcher.and_smaller_than(10, inclusive: true).and_divisible_by(1)
+              expect(10).to match
+            end
+            CODE
+          end
         end
 
         it 'only decides if to include the chained clauses at the time description is invoked' do