diff --git a/transaction/transaction.go b/transaction/transaction.go
index 4139826..6161cb5 100644
--- a/transaction/transaction.go
+++ b/transaction/transaction.go
@@ -1,36 +1,126 @@
 package transaction
 
-import "encoding/json"
+import (
+	"bytes"
+	"encoding/json"
+	"fmt"
+	"reflect"
+)
 
 // Transaction represents a Dredd transaction object.
 // http://dredd.readthedocs.org/en/latest/hooks/#transaction-object-structure
 type Transaction struct {
-	Name     string `json:"name,omitempty"`
-	Host     string `json:"host,omitempty"`
-	Port     string `json:"port,omitempty"`
-	Protocol string `json:"protocol,omitempty"`
-	FullPath string `json:"fullPath,omitempty"`
-	Request  *struct {
-		Body    string                 `json:"body,omitempty"`
-		Headers map[string]interface{} `json:"headers,omitempty"`
-		URI     string                 `json:"uri,omitempty"`
-		Method  string                 `json:"method,omitempty"`
-	} `json:"request,omitempty"`
+	Name     string           `json:"name,omitempty"`
+	Host     string           `json:"host,omitempty"`
+	Port     string           `json:"port,omitempty"`
+	Protocol string           `json:"protocol,omitempty"`
+	FullPath string           `json:"fullPath,omitempty"`
+	Request  *Request         `json:"request,omitempty"`
 	Expected *json.RawMessage `json:"expected,omitempty"`
-	Real     *struct {
-		Body       string                 `json:"body"`
-		Headers    map[string]interface{} `json:"headers"`
-		StatusCode int                    `json:"statusCode"`
-	} `json:"real,omitempty"`
-	Origin  *json.RawMessage `json:"origin,omitempty"`
-	Test    *json.RawMessage `json:"test,omitempty"`
-	Results *json.RawMessage `json:"results,omitempty"`
-	Skip    bool             `json:"skip,omitempty"`
-	Fail    interface{}      `json:"fail,omitempty"`
+	Real     *RealRequest     `json:"real,omitempty"`
+	Origin   *json.RawMessage `json:"origin,omitempty"`
+	Test     *json.RawMessage `json:"test,omitempty"`
+	Results  *json.RawMessage `json:"results,omitempty"`
+	Skip     bool             `json:"skip,omitempty"`
+	Fail     interface{}      `json:"fail,omitempty"`
 
 	TestOrder []string `json:"hooks_modifications,omitempty"`
 }
 
+type Request struct {
+	Body    string  `json:"body,omitempty"`
+	Headers Headers `json:"headers,omitempty"`
+	URI     string  `json:"uri,omitempty"`
+	Method  string  `json:"method,omitempty"`
+}
+
+type RealRequest struct {
+	Body       string  `json:"body"`
+	Headers    Headers `json:"headers"`
+	StatusCode int     `json:"statusCode"`
+}
+
+type Headers map[string][]string
+
+func (hdrs *Headers) MarshalJSON() ([]byte, error) {
+	buf := bytes.Buffer{}
+	buf.WriteByte('{')
+
+	first := true
+	for k, v := range *hdrs {
+		if first {
+			first = false
+		} else {
+			buf.WriteString(",")
+		}
+		numValues := len(v)
+		writeJSONKeyToBuffer(&buf, string(k))
+		if numValues == 1 {
+			writeJSONValueToBuffer(&buf, v[0])
+			continue
+		}
+		data, err := json.Marshal(v)
+
+		if err != nil {
+			return nil, err
+		}
+		buf.WriteString(string(data))
+	}
+	buf.WriteByte('}')
+	return buf.Bytes(), nil
+}
+
+func writeJSONKeyToBuffer(buf *bytes.Buffer, key string) {
+	writeJSONValueToBuffer(buf, key)
+	buf.WriteByte(':')
+}
+
+func writeJSONValueToBuffer(buf *bytes.Buffer, key string) {
+	buf.WriteString(`"` + key + `"`)
+}
+
+func (hdrs *Headers) UnmarshalJSON(data []byte) error {
+	var headers map[string]interface{} = make(map[string]interface{})
+	err := json.Unmarshal(data, &headers)
+
+	if err != nil {
+		return err
+	}
+
+	*hdrs = make(map[string][]string)
+	for k := range headers {
+		header := headers[k]
+		value := reflect.ValueOf(header)
+		kind := value.Kind()
+
+		switch kind {
+		case reflect.Float32, reflect.Float64, reflect.Int, reflect.String:
+			(*hdrs)[k] = []string{
+				stringFromValue(value),
+			}
+		case reflect.Slice:
+			for i := 0; i < value.Len(); i++ {
+				(*hdrs)[k] = append((*hdrs)[k], stringFromValueAtIndex(value, i))
+			}
+
+		default:
+			// TODO: Figure out how to use this
+			panic(fmt.Sprintf("unsupported Kind %s", kind.String()))
+		}
+
+	}
+
+	return nil
+}
+
+func stringFromValueAtIndex(val reflect.Value, index int) string {
+	return fmt.Sprint(val.Index(index).Interface())
+}
+
+func stringFromValue(val reflect.Value) string {
+	return fmt.Sprint(val.Interface())
+}
+
 // AddTestOrderPoint adds a value to the hooks_modification key used when
 // running dredd with TEST_DREDD_HOOKS_HANDLER_ORDER enabled.
 func (t *Transaction) AddTestOrderPoint(value string) {
diff --git a/transaction/transaction_test.go b/transaction/transaction_test.go
index 465b3a1..e4dcde0 100644
--- a/transaction/transaction_test.go
+++ b/transaction/transaction_test.go
@@ -1,6 +1,14 @@
 package transaction
 
-import "testing"
+import (
+	"encoding/json"
+	"reflect"
+	"testing"
+)
+
+type HeadersWrapper struct {
+	Headers Headers `json:"headers,omitempty"`
+}
 
 func TestSettingFailToString(t *testing.T) {
 	trans := Transaction{}
@@ -10,3 +18,66 @@ func TestSettingFailToString(t *testing.T) {
 		t.Errorf("Transaction.Fail member must be able to be set as string")
 	}
 }
+
+func TestHeadersJsonUnmarshal(t *testing.T) {
+	data := []byte(`{
+	    "headers":{
+		"User-Agent":"Dredd/1.4.0 (Darwin 15.4.0; x64)",
+		"Content-Length":11,
+		"Set-Cookie":["Test=Yo"]
+	    }
+	}`)
+
+	hdrs := &HeadersWrapper{}
+	err := json.Unmarshal(data, hdrs)
+	if err != nil {
+		t.Errorf("Error %v", err)
+	}
+
+	if !reflect.DeepEqual(hdrs.Headers["Set-Cookie"], []string{"Test=Yo"}) {
+		t.Errorf("Set-Cookie should be slice with length of 1")
+	}
+
+	if !reflect.DeepEqual(hdrs.Headers["User-Agent"], []string{"Dredd/1.4.0 (Darwin 15.4.0; x64)"}) {
+		t.Errorf("User-Agent should be converted to a slice")
+	}
+
+	if !reflect.DeepEqual(hdrs.Headers["Content-Length"], []string{"11"}) {
+		t.Errorf("Content-Length should be converted to a string and be a slice")
+	}
+}
+
+func TestHeadersMarshalJSON(t *testing.T) {
+	headers := make(map[string][]string)
+	headers["Content-Type"] = []string{"9"}
+	headers["User-Agent"] = []string{"Dredd/1.4.0 (Darwin 15.4.0; x64)"}
+	headers["Set-Cookie"] = []string{"Test=Yo", "Another=This"}
+	wrapper := &HeadersWrapper{
+		Headers: headers,
+	}
+
+	data, err := json.Marshal(wrapper)
+
+	if err != nil {
+		t.Errorf("json.Marshal failed with %v", err)
+	}
+
+	var expected interface{}
+	err = json.Unmarshal([]byte(`{"headers":{"Content-Type":"9","User-Agent":"Dredd/1.4.0 (Darwin 15.4.0; x64)","Set-Cookie":["Test=Yo","Another=This"]}}`), &expected)
+
+	if err != nil {
+		t.Errorf("failed to unmarshal expected json string")
+	}
+
+	var actual interface{}
+	err = json.Unmarshal(data, &actual)
+
+	if err != nil {
+		t.Errorf("failed to unmarshal Marshaled json")
+	}
+
+	if !reflect.DeepEqual(expected, actual) {
+		t.Errorf("json.Marshal failed, data \n %#v did not matched expected \n %#v", actual, expected)
+
+	}
+}