diff --git a/frontend/components/forms/admin/AppConfigForm/AppConfigForm.jsx b/frontend/components/forms/admin/AppConfigForm/AppConfigForm.jsx
index 82ee968e8c..4776fbd108 100644
--- a/frontend/components/forms/admin/AppConfigForm/AppConfigForm.jsx
+++ b/frontend/components/forms/admin/AppConfigForm/AppConfigForm.jsx
@@ -15,6 +15,7 @@ import validate from 'components/forms/admin/AppConfigForm/validate';
 const authMethodOptions = [
   { label: 'Plain', value: 'authmethod_plain' },
   { label: 'Cram MD5', value: 'authmethod_cram_md5' },
+  { label: 'Login', value: 'authmethod_login' },
 ];
 const authTypeOptions = [
   { label: 'Username and Password', value: 'authtype_username_password' },
diff --git a/server/kolide/app.go b/server/kolide/app.go
index bb4e9c0ddc..2ccd7e5717 100644
--- a/server/kolide/app.go
+++ b/server/kolide/app.go
@@ -30,6 +30,7 @@ type AppConfigService interface {
 // SMTPAuthMethod
 const (
 	AuthMethodNameCramMD5        = "authmethod_cram_md5"
+	AuthMethodNameLogin          = "authmethod_login"
 	AuthMethodNamePlain          = "authmethod_plain"
 	AuthTypeNameUserNamePassword = "authtype_username_password"
 	AuthTypeNameNone             = "authtype_none"
@@ -58,6 +59,7 @@ type SMTPAuthMethod int
 const (
 	AuthMethodPlain SMTPAuthMethod = iota
 	AuthMethodCramMD5
+	AuthMethodLogin
 )
 
 func (m SMTPAuthMethod) String() string {
@@ -66,6 +68,8 @@ func (m SMTPAuthMethod) String() string {
 		return AuthMethodNamePlain
 	case AuthMethodCramMD5:
 		return AuthMethodNameCramMD5
+	case AuthMethodLogin:
+		return AuthMethodNameLogin
 	default:
 		return ""
 	}
diff --git a/server/mail/mail.go b/server/mail/mail.go
index 345b51ab83..e9aa926c57 100644
--- a/server/mail/mail.go
+++ b/server/mail/mail.go
@@ -6,6 +6,7 @@ import (
 	"fmt"
 	"net"
 	"net/smtp"
+	"strings"
 	"time"
 
 	"github.com/kolide/fleet/server/kolide"
@@ -70,6 +71,35 @@ func (m mailService) SendEmail(e kolide.Email) error {
 	return m.sendMail(e, msg)
 }
 
+type loginauth struct {
+	username string
+	password string
+}
+
+func LoginAuth(username, password string) smtp.Auth {
+	return &loginauth{username: username, password: password}
+}
+
+func (l *loginauth) Start(serverInfo *smtp.ServerInfo) (proto string, toServer []byte, err error) {
+	return "LOGIN", nil, nil
+}
+
+func (l *loginauth) Next(fromServer []byte, more bool) (toServer []byte, err error) {
+	if !more {
+		return nil, nil
+	}
+
+	prompt := strings.TrimSpace(string(fromServer))
+	switch prompt {
+	case "Username:":
+		return []byte(l.username), nil
+	case "Password:":
+		return []byte(l.password), nil
+	default:
+		return nil, errors.New("unexpected LOGIN prompt from server")
+	}
+}
+
 func smtpAuth(e kolide.Email) (smtp.Auth, error) {
 	if e.Config.SMTPAuthenticationType != kolide.AuthTypeUserNamePassword {
 		return nil, nil
@@ -80,6 +110,8 @@ func smtpAuth(e kolide.Email) (smtp.Auth, error) {
 		auth = smtp.CRAMMD5Auth(e.Config.SMTPUserName, e.Config.SMTPPassword)
 	case kolide.AuthMethodPlain:
 		auth = smtp.PlainAuth("", e.Config.SMTPUserName, e.Config.SMTPPassword, e.Config.SMTPServer)
+	case kolide.AuthMethodLogin:
+		auth = LoginAuth(e.Config.SMTPUserName, e.Config.SMTPPassword)
 	default:
 		return nil, fmt.Errorf("unknown SMTP auth type '%d'", e.Config.SMTPAuthenticationMethod)
 	}
diff --git a/server/service/service_appconfig.go b/server/service/service_appconfig.go
index f922861915..f2d2ec8e6e 100644
--- a/server/service/service_appconfig.go
+++ b/server/service/service_appconfig.go
@@ -150,6 +150,8 @@ func appConfigFromAppConfigPayload(p kolide.AppConfigPayload, config kolide.AppC
 				config.SMTPAuthenticationMethod = kolide.AuthMethodCramMD5
 			case kolide.AuthMethodNamePlain:
 				config.SMTPAuthenticationMethod = kolide.AuthMethodPlain
+			case kolide.AuthMethodNameLogin:
+				config.SMTPAuthenticationMethod = kolide.AuthMethodLogin
 			default:
 				panic("unknown SMTP AuthMethod: " + *p.SMTPAuthenticationMethod)
 			}