diff --git a/Src/FluentAssertions/Primitives/StringEqualityValidator.cs b/Src/FluentAssertions/Primitives/StringEqualityValidator.cs
index 5b749649e4..9bfc29ebc3 100644
--- a/Src/FluentAssertions/Primitives/StringEqualityValidator.cs
+++ b/Src/FluentAssertions/Primitives/StringEqualityValidator.cs
@@ -27,14 +27,56 @@ protected override bool ValidateAgainstSuperfluousWhitespace()
 
         protected override bool ValidateAgainstLengthDifferences()
         {
+            // Logic is a little bit convoluted because I want to avoid calculation
+            // of mismatch segment in case of equalLength == true for performance reason.
+            // If lazy version of FailWith would be introduced, calculation of mismatch
+            // segment can be moved directly to FailWith's argument
+            bool equalLength = subject.Length == expected.Length;
+
+            string mismatchSegment = GetMismatchSegmentForStringsOfDifferentLengths(equalLength);
+
             return assertion
-                .ForCondition(subject.Length == expected.Length)
+                .ForCondition(equalLength)
                 .FailWith(
-                    ExpectationDescription + "{0} with a length of {1}{reason}, but {2} has a length of {3}.",
+                    ExpectationDescription + "{0} with a length of {1}{reason}, but {2} has a length of {3}, differs near " + mismatchSegment +  ".",
                     expected, expected.Length, subject, subject.Length)
                 .SourceSucceeded;
         }
 
+        private string GetMismatchSegmentForStringsOfDifferentLengths(bool equalLength)
+        {
+            if (equalLength)
+            {
+                return "";
+            }
+
+            int indexOfMismatch = subject.IndexOfFirstMismatch(expected, comparisonMode);
+
+            // If there is no difference it means that either
+            // * subject starts with expected or
+            // * expected starts with subject
+            if (indexOfMismatch == -1)
+            {
+                // If subject is shorter we are sure that expected starts with subject
+                if (subject.Length < expected.Length)
+                {
+                    // Subject is shorter so we point at its last character.
+                    // We would like to point at next character as it is the real
+                    // index of first mismatch, but we need to point at character existing in
+                    // subject, so the next best thing is the last subject character.
+                    indexOfMismatch = Math.Max(0, subject.Length - 1);
+                }
+                else
+                {
+                    // If subject is longer we are sure that subject starts with expected
+                    // and we point at first character after expected.
+                    indexOfMismatch = expected.Length;
+                }
+            }
+
+            return subject.IndexedSegmentAt(indexOfMismatch);
+        }
+
         protected override void ValidateAgainstMismatch()
         {
             int indexOfMismatch = subject.IndexOfFirstMismatch(expected, comparisonMode);
diff --git a/Tests/Shared.Specs/BasicEquivalencySpecs.cs b/Tests/Shared.Specs/BasicEquivalencySpecs.cs
index 23965aaeef..06992c36ff 100644
--- a/Tests/Shared.Specs/BasicEquivalencySpecs.cs
+++ b/Tests/Shared.Specs/BasicEquivalencySpecs.cs
@@ -644,7 +644,7 @@ public void
             // Assert
             //-----------------------------------------------------------------------------------------------------------
             act.Should().Throw<XunitException>().WithMessage(
-                @"Expected member Member1 to be*""different"" with a length of 9, but*"""" has a length of 0.*");
+                @"Expected member Member1 to be*""different"" with a length of 9, but*"""" has a length of 0*");
         }
 
         [Fact]
diff --git a/Tests/Shared.Specs/StringAssertionSpecs.cs b/Tests/Shared.Specs/StringAssertionSpecs.cs
index f980fb63ba..7d56e4e959 100644
--- a/Tests/Shared.Specs/StringAssertionSpecs.cs
+++ b/Tests/Shared.Specs/StringAssertionSpecs.cs
@@ -65,8 +65,7 @@ public void When_the_expected_string_is_shorter_than_the_actual_string_it_should
             //-----------------------------------------------------------------------------------------------------------
             // Assert
             //-----------------------------------------------------------------------------------------------------------
-            act.Should().Throw<XunitException>().WithMessage(
-                "Expected string to be \"AB\" with a length of 2, but \"ABC\" has a length of 3.");
+            act.Should().Throw<XunitException>().WithMessage("*index 2*");
         }
 
         [Fact]
@@ -80,8 +79,35 @@ public void When_the_expected_string_is_longer_than_the_actual_string_it_should_
             //-----------------------------------------------------------------------------------------------------------
             // Assert
             //-----------------------------------------------------------------------------------------------------------
-            act.Should().Throw<XunitException>().WithMessage(
-                "Expected string to be \"ABC\" with a length of 3, but \"AB\" has a length of 2.");
+            act.Should().Throw<XunitException>().WithMessage("*index 1*");
+        }
+
+        [Fact]
+        public void When_the_expected_string_is_empty_it_should_throw()
+        {
+            //-----------------------------------------------------------------------------------------------------------
+            // Act
+            //-----------------------------------------------------------------------------------------------------------
+            Action act = () => "ABC".Should().Be("");
+
+            //-----------------------------------------------------------------------------------------------------------
+            // Assert
+            //-----------------------------------------------------------------------------------------------------------
+            act.Should().Throw<XunitException>().WithMessage("*index 0*");
+        }
+
+        [Fact]
+        public void When_the_subject_string_is_empty_it_should_throw()
+        {
+            //-----------------------------------------------------------------------------------------------------------
+            // Act
+            //-----------------------------------------------------------------------------------------------------------
+            Action act = () => "".Should().Be("ABC");
+
+            //-----------------------------------------------------------------------------------------------------------
+            // Assert
+            //-----------------------------------------------------------------------------------------------------------
+            act.Should().Throw<XunitException>().WithMessage("*index 0*");
         }
 
         [Fact]
@@ -1904,7 +1930,7 @@ public void When_non_empty_string_is_expected_to_be_equivalent_to_empty_it_shoul
             // Assert
             //-----------------------------------------------------------------------------------------------------------
             act.Should().Throw<XunitException>().WithMessage(
-                "Expected string to be equivalent to \"\" with a length of 0, but \"ABC\" has a length of 3.");
+                "Expected string to be equivalent to \"\" with a length of 0, but \"ABC\" has a length of 3, differs near \"ABC\" (index 0).");
         }
 
         [Fact]
diff --git a/docs/_pages/documentation.md b/docs/_pages/documentation.md
index 40b6977e6d..60e46554d5 100644
--- a/docs/_pages/documentation.md
+++ b/docs/_pages/documentation.md
@@ -1290,7 +1290,7 @@ The above will batch the two failures, and throw an exception at the point of di
 E.g. Exception thrown at point of dispose contains:
 
     Expected value to be 10, but found 5.
-    Expected string to be "Expected" with a length of 8, but "Actual" has a length of 6.
+    Expected string to be "Expected" with a length of 8, but "Actual" has a length of 6, differs near "Act" (index 0).
     
         at........