diff --git a/lib/rspec/matchers/built_in/compound.rb b/lib/rspec/matchers/built_in/compound.rb
index 56f27b1a6..0c07d8ba2 100644
--- a/lib/rspec/matchers/built_in/compound.rb
+++ b/lib/rspec/matchers/built_in/compound.rb
@@ -75,6 +75,8 @@ def initialize_copy(other)
         end
 
         def match(_expected, actual)
+          @matcher_1_matches = nil
+          @matcher_2_matches = nil
           evaluator_klass = if supports_block_expectations? && Proc === actual
                               NestedEvaluator
                             else
@@ -97,11 +99,13 @@ def compound_failure_message
         end
 
         def matcher_1_matches?
-          evaluator.matcher_matches?(matcher_1)
+          return @matcher_1_matches unless @matcher_1_matches.nil?
+          @matcher_1_matches = evaluator.matcher_matches?(matcher_1)
         end
 
         def matcher_2_matches?
-          evaluator.matcher_matches?(matcher_2)
+          return @matcher_2_matches unless @matcher_2_matches.nil?
+          @matcher_2_matches = evaluator.matcher_matches?(matcher_2)
         end
 
         def matcher_supports_block_expectations?(matcher)
diff --git a/spec/rspec/matchers/built_in/compound_spec.rb b/spec/rspec/matchers/built_in/compound_spec.rb
index 0594b6b0a..a562b7eeb 100644
--- a/spec/rspec/matchers/built_in/compound_spec.rb
+++ b/spec/rspec/matchers/built_in/compound_spec.rb
@@ -872,6 +872,52 @@ def expect_block
           |
         EOS
       end
+
+      context "with long chains of compound matchers" do
+        let(:failing_matcher) { include(not_expected) }
+        let(:passing_matcher) { include(expected) }
+        let(:expected) { actual }
+        let(:not_expected) { 3 }
+        let(:actual) { 4 }
+
+        context "with a failing first matcher" do
+          it "generates a failure description quickly" do
+            timeout_if_not_debugging(0.2) do
+              compound = failing_matcher
+              15.times { compound = compound.and(passing_matcher) }
+              expect { expect([actual]).to compound }.to fail_including("expected [#{actual}] to include #{not_expected}")
+            end
+          end
+        end
+
+        context "with a failing last matcher" do
+          it "generates a failure description quickly" do
+            timeout_if_not_debugging(0.2) do
+              compound  = failing_matcher
+              15.times { compound = passing_matcher.and(compound) }
+              expect { expect([actual]).to compound }.to fail_including("expected [#{actual}] to include #{not_expected}")
+            end
+          end
+        end
+
+        context "with all failing matchers" do
+          it "generates a failure description quickly with and" do
+            timeout_if_not_debugging(0.2) do
+              compound = failing_matcher
+              15.times { compound = compound.and(failing_matcher) }
+              expect { expect([actual]).to compound }.to fail_including("expected [#{actual}] to include #{not_expected}")
+            end
+          end
+
+          it "generates a failure description quickly with or" do
+            timeout_if_not_debugging(0.2) do
+              compound = failing_matcher
+              15.times { compound = compound.or(failing_matcher) }
+              expect { expect([actual]).to compound }.to fail_including("expected [#{actual}] to include #{not_expected}")
+            end
+          end
+        end
+      end
     end
 
     describe "expect(...).not_to matcher.or(other_matcher)" do
diff --git a/spec/rspec/matchers/built_in/contain_exactly_spec.rb b/spec/rspec/matchers/built_in/contain_exactly_spec.rb
index ac1996ae8..5d48c77f0 100644
--- a/spec/rspec/matchers/built_in/contain_exactly_spec.rb
+++ b/spec/rspec/matchers/built_in/contain_exactly_spec.rb
@@ -184,14 +184,6 @@ def array.send; :sent; end
 MESSAGE
   end
 
-  def timeout_if_not_debugging(time)
-    in_sub_process_if_possible do
-      require 'timeout'
-      return yield if defined?(::Debugger)
-      Timeout.timeout(time) { yield }
-    end
-  end
-
   it 'fails a match of 11 items with duplicates in a reasonable amount of time' do
     timeout_if_not_debugging(0.1) do
       expected = [0, 1, 1,    3, 3, 3,    4, 4,    8, 8, 9   ]
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index 595fafa2c..bb5a59486 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -25,6 +25,14 @@ def dedent(string)
     string.gsub(/^\s+\|/, '').chomp
   end
 
+  def timeout_if_not_debugging(time)
+    in_sub_process_if_possible do
+      require 'timeout'
+      return yield if defined?(::Debugger)
+      Timeout.timeout(time) { yield }
+    end
+  end
+
   # We have to use Hash#inspect in examples that have multi-entry
   # hashes because the #inspect output on 1.8.7 is non-deterministic
   # due to the fact that hashes are not ordered. So we can't simply