diff --git a/commands/commands.go b/commands/commands.go
index b0b6b26d..41b4d3c0 100644
--- a/commands/commands.go
+++ b/commands/commands.go
@@ -141,6 +141,9 @@ func logPanic(loggedError error, recursive bool) string {
 
 	if wErr, ok := loggedError.(ErrorWithStack); ok {
 		fmt.Fprintln(fmtWriter, wErr.InnerError())
+		for key, value := range wErr.Context() {
+			fmt.Fprintf(fmtWriter, "%s=%s\n", key, value)
+		}
 		fmtWriter.Write(wErr.Stack())
 	} else {
 		fmtWriter.Write(gitmedia.Stack())
@@ -155,6 +158,7 @@ func logPanic(loggedError error, recursive bool) string {
 }
 
 type ErrorWithStack interface {
+	Context() map[string]string
 	InnerError() string
 	Stack() []byte
 }
diff --git a/gitmedia/errors.go b/gitmedia/errors.go
index df4f1489..d64d7f8e 100644
--- a/gitmedia/errors.go
+++ b/gitmedia/errors.go
@@ -9,6 +9,7 @@ type WrappedError struct {
 	Err     error
 	Message string
 	stack   []byte
+	context map[string]string
 }
 
 func Error(err error) *WrappedError {
@@ -33,6 +34,27 @@ func Errorf(err error, format string, args ...interface{}) *WrappedError {
 	return e
 }
 
+func (e *WrappedError) Set(key, value string) {
+	if e.context == nil {
+		e.context = make(map[string]string)
+	}
+	e.context[key] = value
+}
+
+func (e *WrappedError) Get(key string) string {
+	if e.context == nil {
+		return ""
+	}
+	return e.context[key]
+}
+
+func (e *WrappedError) Del(key string) {
+	if e.context == nil {
+		return
+	}
+	delete(e.context, key)
+}
+
 func (e *WrappedError) Error() string {
 	return e.Message
 }
@@ -49,6 +71,13 @@ func (e *WrappedError) Stack() []byte {
 	return e.stack
 }
 
+func (e *WrappedError) Context() map[string]string {
+	if e.context == nil {
+		e.context = make(map[string]string)
+	}
+	return e.context
+}
+
 func Stack() []byte {
 	stackBuf := make([]byte, 1024*1024)
 	written := runtime.Stack(stackBuf, false)
diff --git a/gitmediaclient/client.go b/gitmediaclient/client.go
index 757cdb89..d1042d03 100644
--- a/gitmediaclient/client.go
+++ b/gitmediaclient/client.go
@@ -98,10 +98,10 @@ func Get(filename string) (io.ReadCloser, int64, *gitmedia.WrappedError) {
 	}
 
 	req.Header.Set("Accept", gitMediaType)
-	res, err := doRequest(req, creds)
+	res, wErr := doRequest(req, creds)
 
 	if err != nil {
-		return nil, 0, gitmedia.Error(err)
+		return nil, 0, wErr
 	}
 
 	contentType := res.Header.Get("Content-Type")
@@ -146,7 +146,7 @@ func validateMediaHeader(contentType string, reader io.Reader) (bool, error) {
 	return true, nil
 }
 
-func doRequest(req *http.Request, creds Creds) (*http.Response, error) {
+func doRequest(req *http.Request, creds Creds) (*http.Response, *gitmedia.WrappedError) {
 	res, err := http.DefaultClient.Do(req)
 
 	if err == nil {
@@ -159,16 +159,21 @@ func doRequest(req *http.Request, creds Creds) (*http.Response, error) {
 			apierr := &Error{}
 			dec := json.NewDecoder(res.Body)
 			if err := dec.Decode(apierr); err != nil {
-				return res, err
+				return res, gitmedia.Errorf(err, "Error decoding JSON from response")
 			}
 
-			return res, apierr
+			return res, gitmedia.Errorf(apierr, "Invalid response: %d", res.StatusCode)
 		}
 
 		execCreds(creds, "approve")
 	}
 
-	return res, err
+	wErr := gitmedia.Errorf(err, "Error sending HTTP request to %s", req.URL.String())
+	wErr.Set("URL", req.URL.String())
+	for key, _ := range req.Header {
+		wErr.Set(key, req.Header.Get(key))
+	}
+	return res, wErr
 }
 
 func clientRequest(method, oid string) (*http.Request, Creds, error) {