diff --git a/mailHelper.go b/mailHelper.go
index 36d623b..6173aee 100644
--- a/mailHelper.go
+++ b/mailHelper.go
@@ -24,13 +24,20 @@ func send(e Email, api keybase.ChatAPI) {
 	log.LogDebug(message)
 	log.LogInfo("Sending message")
 	chat.React(api.Msg.ID, ":mailbox_with_no_mail:")
+	if conf.KeyPass == "" {
+		chat.React(api.Msg.ID, ":unlock:")
+	} else {
+		chat.React(api.Msg.ID, ":lock_with_ink_pen:")
+	}
 	err := smtp.SendMail(conf.SmtpServer,
 		smtp.PlainAuth("", conf.MyEmail, conf.EmailPass, conf.AuthServer),
 		conf.MyEmail, e.Recipients, []byte(message))
+	chat.React(api.Msg.ID, ":mailbox_with_no_mail:")
 	if err != nil {
 		log.LogErrorType(err)
+		chat.React(api.Msg.ID, ":warning:")
+		return
 	}
-	chat.React(api.Msg.ID, ":mailbox_with_no_mail:")
 	chat.React(api.Msg.ID, ":mailbox_with_mail:")
 	log.LogInfo("Email Sent")
 }
diff --git a/main.go b/main.go
index 78cf18e..ad2cbbf 100644
--- a/main.go
+++ b/main.go
@@ -131,16 +131,22 @@ func loadConfig() Config {
 	return c
 }
 func setupCredentials() {
-	log.LogCritical("Enter pgp key passphrase:")
+	log.LogCritical("Enter optional pgp key passphrase:")
 	bytePass, err := terminal.ReadPassword(int(syscall.Stdin))
 	if err != nil {
 		log.LogCritical(fmt.Sprintf("Error reading pgp password:\n```%+v```", err))
 	}
 	conf.KeyPass = strings.TrimSpace(string(bytePass))
-	log.LogCritical("Enter email passphrase:")
-	bytePass, err = terminal.ReadPassword(int(syscall.Stdin))
-	if err != nil {
-		log.LogCritical(fmt.Sprintf("Error reading email password:\n```%+v```", err))
+	if conf.KeyPass == "" {
+		log.LogCritical("Starting without PGP signature capabilities.")
+	}
+	for i := len(conf.EmailPass); i < 1; i = len(conf.EmailPass) {
+		log.LogCritical("Enter required email passphrase:")
+		bytePass, err = terminal.ReadPassword(int(syscall.Stdin))
+		if err != nil {
+			log.LogCritical(fmt.Sprintf("Error reading email password:\n```%+v```", err))
+		}
+		conf.EmailPass = strings.TrimSpace(string(bytePass))
+
 	}
-	conf.EmailPass = strings.TrimSpace(string(bytePass))
 }
diff --git a/pgpHelper.go b/pgpHelper.go
index 2f579d4..5c434be 100644
--- a/pgpHelper.go
+++ b/pgpHelper.go
@@ -39,6 +39,9 @@ func getPrivateKey() *openpgp.Entity {
 }
 
 func signMessage(m string) string {
+	if conf.KeyPass == "" {
+		return m
+	}
 	pk := getPrivateKey()
 	out := new(bytes.Buffer)
 	in, err := clearsign.Encode(out, pk.PrivateKey, nil)