diff --git a/matchers.go b/matchers.go
index 223f6ef53..dc2706331 100644
--- a/matchers.go
+++ b/matchers.go
@@ -485,10 +485,15 @@ func Not(matcher types.GomegaMatcher) types.GomegaMatcher {
 }
 
 //WithTransform applies the `transform` to the actual value and matches it against `matcher`.
-//The given transform must be a function of one parameter that returns one value.
+//The given transform must be either a function of one parameter that returns one value or a
+// function of one parameter that returns two values, where the second value must be of the
+// error type.
 //  var plus1 = func(i int) int { return i + 1 }
 //  Expect(1).To(WithTransform(plus1, Equal(2))
 //
+//   var failingplus1 = func(i int) (int, error) { return 42, "this does not compute" }
+//   Expect(1).To(WithTrafo(failingplus1, Equal(2)))
+//
 //And(), Or(), Not() and WithTransform() allow matchers to be composed into complex expressions.
 func WithTransform(transform interface{}, matcher types.GomegaMatcher) types.GomegaMatcher {
 	return matchers.NewWithTransformMatcher(transform, matcher)
diff --git a/matchers/with_transform.go b/matchers/with_transform.go
index 8a06bd384..07caa5bfa 100644
--- a/matchers/with_transform.go
+++ b/matchers/with_transform.go
@@ -9,7 +9,7 @@ import (
 
 type WithTransformMatcher struct {
 	// input
-	Transform interface{} // must be a function of one parameter that returns one value
+	Transform interface{} // must be a function of one parameter that returns one value and an optional error
 	Matcher   types.GomegaMatcher
 
 	// cached value
@@ -19,6 +19,9 @@ type WithTransformMatcher struct {
 	transformedValue interface{}
 }
 
+// reflect.Type for error
+var errorT = reflect.TypeOf((*error)(nil)).Elem()
+
 func NewWithTransformMatcher(transform interface{}, matcher types.GomegaMatcher) *WithTransformMatcher {
 	if transform == nil {
 		panic("transform function cannot be nil")
@@ -27,8 +30,10 @@ func NewWithTransformMatcher(transform interface{}, matcher types.GomegaMatcher)
 	if txType.NumIn() != 1 {
 		panic("transform function must have 1 argument")
 	}
-	if txType.NumOut() != 1 {
-		panic("transform function must have 1 return value")
+	if numout := txType.NumOut(); numout != 1 {
+		if numout != 2 || !txType.Out(1).AssignableTo(errorT) {
+			panic("transform function must either have 1 return value, or 1 return value plus 1 error value")
+		}
 	}
 
 	return &WithTransformMatcher{
@@ -57,6 +62,11 @@ func (m *WithTransformMatcher) Match(actual interface{}) (bool, error) {
 	// call the Transform function with `actual`
 	fn := reflect.ValueOf(m.Transform)
 	result := fn.Call([]reflect.Value{param})
+	if len(result) == 2 {
+		if !result[1].IsNil() {
+			return false, fmt.Errorf("Transform function failed: %e", result[1].Interface())
+		}
+	}
 	m.transformedValue = result[0].Interface() // expect exactly one value
 
 	return m.Matcher.Match(m.transformedValue)
diff --git a/matchers/with_transform_test.go b/matchers/with_transform_test.go
index 38436fe75..570cd7c33 100644
--- a/matchers/with_transform_test.go
+++ b/matchers/with_transform_test.go
@@ -35,6 +35,11 @@ var _ = Describe("WithTransformMatcher", func() {
 				panicsWithTransformer(func(i int) (int, int) { return 5, 6 })
 			})
 		})
+		Context("Invalid number of return values, but correct number of arguments", func() {
+			It("Two return values, but second return value not an error", func() {
+				panicsWithTransformer(func(interface{}) (int, int) { return 5, 6 })
+			})
+		})
 	})
 
 	When("the actual value is incompatible", func() {
@@ -121,6 +126,16 @@ var _ = Describe("WithTransformMatcher", func() {
 			})
 		})
 
+		When("transform fails", func() {
+			It("reports the transformation error", func() {
+				actual, trafo := "foo", func(string) (string, error) { return "", errors.New("that does not transform") }
+				success, err := WithTransform(trafo, Equal(actual)).Match(actual)
+				Expect(success).To(BeFalse())
+				Expect(err).To(HaveOccurred())
+				Expect(err.Error()).To(ContainSubstring("that does not transform"))
+			})
+		})
+
 		Context("actual value is incompatible with transform function's argument type", func() {
 			It("gracefully fails if transform cannot be performed", func() {
 				m := WithTransform(plus1, Equal(3))