diff --git a/matchers/match_json_matcher.go b/matchers/match_json_matcher.go
index efc5e15..86b1ca6 100644
--- a/matchers/match_json_matcher.go
+++ b/matchers/match_json_matcher.go
@@ -4,8 +4,9 @@
 	"bytes"
 	"encoding/json"
 	"fmt"
-	"github.com/onsi/gomega/format"
 	"reflect"
+
+	"github.com/onsi/gomega/format"
 )
 
 type MatchJSONMatcher struct {
@@ -50,11 +51,11 @@
 	ebuf := new(bytes.Buffer)
 
 	if err := json.Indent(abuf, []byte(actualString), "", "  "); err != nil {
-		return "", "", err
+		return "", "", fmt.Errorf("Actual '%s' should be valid JSON, but it is not.\nUnderlying error:%s", actualString, err)
 	}
 
 	if err := json.Indent(ebuf, []byte(expectedString), "", "  "); err != nil {
-		return "", "", err
+		return "", "", fmt.Errorf("Expected '%s' should be valid JSON, but it is not.\nUnderlying error:%s", expectedString, err)
 	}
 
 	return abuf.String(), ebuf.String(), nil
diff --git a/matchers/match_json_matcher_test.go b/matchers/match_json_matcher_test.go
index c1924ba..1fbf151 100644
--- a/matchers/match_json_matcher_test.go
+++ b/matchers/match_json_matcher_test.go
@@ -25,15 +25,21 @@
 		})
 	})
 
-	Context("when either side is not valid JSON", func() {
-		It("should error", func() {
+	Context("when the expected is not valid JSON", func() {
+		It("should error and explain why", func() {
+			success, err := (&MatchJSONMatcher{JSONToMatch: `{}`}).Match(`oops`)
+			Ω(success).Should(BeFalse())
+			Ω(err).Should(HaveOccurred())
+			Ω(err.Error()).Should(ContainSubstring("Actual 'oops' should be valid JSON"))
+		})
+	})
+
+	Context("when the actual is not valid JSON", func() {
+		It("should error and explain why", func() {
 			success, err := (&MatchJSONMatcher{JSONToMatch: `oops`}).Match(`{}`)
 			Ω(success).Should(BeFalse())
 			Ω(err).Should(HaveOccurred())
-
-			success, err = (&MatchJSONMatcher{JSONToMatch: `{}`}).Match(`oops`)
-			Ω(success).Should(BeFalse())
-			Ω(err).Should(HaveOccurred())
+			Ω(err.Error()).Should(ContainSubstring("Expected 'oops' should be valid JSON"))
 		})
 	})