diff --git a/commands/deploy.go b/commands/deploy.go
index 408405dc..513ffb61 100644
--- a/commands/deploy.go
+++ b/commands/deploy.go
@@ -75,7 +75,7 @@ func (d *KoolDeploy) Execute(args []string) (err error) {
 		api.SetBaseURL(url)
 	}
 
-	d.Shell().Println("Create release file...")
+	d.Shell().Info("Create release file...")
 	if filename, err = d.createReleaseFile(); err != nil {
 		return
 	}
@@ -89,14 +89,14 @@ func (d *KoolDeploy) Execute(args []string) (err error) {
 
 	deploy = api.NewDeploy(filename)
 
-	d.Shell().Println("Upload release file...")
+	d.Shell().Info("Upload release file...")
 	if err = deploy.SendFile(); err != nil {
 		return
 	}
 
 	d.Shell().Println("Going to deploy...")
 
-	timeout := 10 * time.Minute
+	timeout := 30 * time.Minute
 
 	if min, err := strconv.Atoi(d.env.Get("KOOL_API_TIMEOUT")); err == nil {
 		timeout = time.Duration(min) * time.Minute
diff --git a/services/cloud/api/deploy.go b/services/cloud/api/deploy.go
index a41ac41b..220b9c75 100644
--- a/services/cloud/api/deploy.go
+++ b/services/cloud/api/deploy.go
@@ -63,6 +63,7 @@ func (d *Deploy) SendFile() (err error) {
 			if errAPI.Status == http.StatusUnauthorized {
 				err = ErrUnauthorized
 			} else if errAPI.Status == http.StatusUnprocessableEntity {
+				fmt.Println(err)
 				err = ErrPayloadValidation
 			} else if errAPI.Status != http.StatusOK && errAPI.Status != http.StatusCreated {
 				err = ErrBadResponseStatus
diff --git a/services/cloud/api/endpoint.go b/services/cloud/api/endpoint.go
index 128a4e9a..8f5f1cd9 100644
--- a/services/cloud/api/endpoint.go
+++ b/services/cloud/api/endpoint.go
@@ -112,7 +112,7 @@ func (e *DefaultEndpoint) DoCall() (err error) {
 	reqURL := fmt.Sprintf("%s/%s?%s", apiBaseURL, e.path, e.query.Encode())
 
 	if verbose {
-		fmt.Fprintf(os.Stderr, "api - calling URL: %s\n", reqURL)
+		fmt.Fprintf(os.Stderr, "[Kool Cloud] Going to call: %s\n", reqURL)
 	}
 
 	if request, err = http.NewRequest(e.method, reqURL, body); err != nil {
@@ -137,7 +137,7 @@ func (e *DefaultEndpoint) DoCall() (err error) {
 	}
 
 	if verbose {
-		fmt.Fprintf(os.Stderr, "api - got response: %s\n", string(raw))
+		fmt.Fprintf(os.Stderr, "[Kool Cloud] Got: %s\n", string(raw))
 	}
 
 	if e.statusCode >= 400 {
diff --git a/services/cloud/api/errors.go b/services/cloud/api/errors.go
index 3aca1bf0..f3ceea01 100644
--- a/services/cloud/api/errors.go
+++ b/services/cloud/api/errors.go
@@ -3,6 +3,7 @@ package api
 import (
 	"errors"
 	"fmt"
+	"strings"
 )
 
 // ErrBadAPIServer represents some issue in the API side
@@ -17,7 +18,7 @@ var ErrDeployFailed error
 // ErrUnauthorized unauthorized; please check your KOOL_API_TOKEN
 var ErrUnauthorized error
 
-// ErrPayloadValidation something went wrong validating the payload
+// failed validating deploy payload
 var ErrPayloadValidation error
 
 // ErrBadResponseStatus unexpected return status
@@ -28,25 +29,29 @@ var ErrUnexpectedResponse error
 
 // ErrAPI reprents a default error returned from the API
 type ErrAPI struct {
-	Status  int
-	Message string `json:"message"`
+	Status int
 
-	Errors map[string]interface{} `json:"errors"`
+	Message string                 `json:"message"`
+	Errors  map[string]interface{} `json:"errors"`
 }
 
 // Error returns the string representation for the error
 func (e *ErrAPI) Error() string {
 	if e.Errors != nil {
-		return fmt.Sprintf("%d - %s (%v)", e.Status, e.Message, e.Errors)
+		s := []string{}
+		for k, e := range e.Errors {
+			s = append(s, fmt.Sprintf("\t%s > %v", k, e.([]interface{})[0]))
+		}
+		return fmt.Sprintf("\n%d - %s\n\n%s\n", e.Status, e.Message, strings.Join(s, "\n"))
 	}
-	return fmt.Sprintf("%d - %s", e.Status, e.Message)
+	return fmt.Sprintf("\n%d - %s\n", e.Status, e.Message)
 }
 
 func init() {
 	ErrBadAPIServer = errors.New("bad API server response")
 	ErrDeployFailed = errors.New("deploy process has failed")
 	ErrUnauthorized = errors.New("unauthorized; please check your KOOL_API_TOKEN")
-	ErrPayloadValidation = errors.New("something went wrong validating the payload")
+	ErrPayloadValidation = errors.New("failed validating deploy payload")
 	ErrBadResponseStatus = errors.New("unexpected return status")
 	ErrUnexpectedResponse = errors.New("bad API response; please ask for support")
 	ErrMissingToken = errors.New("missing KOOL_API_TOKEN")
diff --git a/services/cloud/api/errors_test.go b/services/cloud/api/errors_test.go
index f2de56cb..d82c7a0f 100644
--- a/services/cloud/api/errors_test.go
+++ b/services/cloud/api/errors_test.go
@@ -25,13 +25,15 @@ func TestDefinedErrors(t *testing.T) {
 func TestApiErr(t *testing.T) {
 	err := &ErrAPI{100, "message", nil}
 
-	if err.Error() != "100 - message" {
+	if err.Error() != "\n100 - message\n" {
 		t.Errorf("unexpected error message: %s", err.Error())
 	}
 
-	err.Errors = make(map[string]interface{})
+	err.Errors = map[string]interface{}{
+		"foo": []interface{}{"bar"},
+	}
 
-	if err.Error() != "100 - message (map[])" {
+	if err.Error() != "\n100 - message\n\n\tfoo > bar\n" {
 		t.Errorf("unexpected error message: %s", err.Error())
 	}
 }