diff --git a/src/main/java/com/socrata/datasync/SMTPMailer.java b/src/main/java/com/socrata/datasync/SMTPMailer.java
index a7a8d4f..edf9d76 100644
--- a/src/main/java/com/socrata/datasync/SMTPMailer.java
+++ b/src/main/java/com/socrata/datasync/SMTPMailer.java
@@ -62,19 +62,18 @@ public static void send(String recipientEmail, String ccEmail, String title, Str
 
         // Get a Properties object
         Properties props = System.getProperties();
-        props.setProperty("mail.smtps.host", userPrefs.getOutgoingMailServer());
-        props.setProperty("mail.smtp.socketFactory.fallback", "false");
-        props.setProperty("mail.smtp.port", userPrefs.getSmtpPort());
         String sslPort = userPrefs.getSslPort();
-
         boolean useSSL = !(sslPort.equals(""));
 
+        boolean hasPwd = userPrefs.getSmtpPassword() != null && !userPrefs.getSmtpPassword().isEmpty();
 
         if(useSSL) {
-
-            props.setProperty("mail.smtp.socketFactory.class", SSL_FACTORY);
-            props.setProperty("mail.smtp.socketFactory.port", sslPort);
-            props.setProperty("mail.smtps.auth", "true");
+            props.setProperty("mail.smtps.host", userPrefs.getOutgoingMailServer());
+            props.setProperty("mail.smtps.socketFactory.fallback", "false");
+            props.setProperty("mail.smtps.port", sslPort);
+            props.setProperty("mail.smtps.socketFactory.class", SSL_FACTORY);
+            props.setProperty("mail.smtps.socketFactory.port", sslPort);
+            props.setProperty("mail.smtps.auth", hasPwd ? "true" : "false");
             /*
         If set to false, the QUIT command is sent and the connection is immediately closed. If set
         to true (the default), causes the transport to wait for the response to the QUIT command.
@@ -83,9 +82,16 @@ to true (the default), causes the transport to wait for the response to the QUIT
                 http://forum.java.sun.com/thread.jspa?threadID=5205249
                 smtpsend.java - demo program from javamail
         */
-            props.put("mail.smtps.quitwait", "false");
+            props.setProperty("mail.smtps.quitwait", "false");
+        } else {
+            props.setProperty("mail.smtp.host", userPrefs.getOutgoingMailServer());
+            props.setProperty("mail.smtp.socketFactory.fallback", "false");
+            props.setProperty("mail.smtp.port", userPrefs.getSmtpPort());
+            props.setProperty("mail.smtp.auth", hasPwd ? "true" : "false");
+            props.setProperty("mail.smtp.quitwait", "false");
         }
 
+
         Session session = Session.getInstance(props, null);
 
         // -- Create a new message --
@@ -111,12 +117,14 @@ to true (the default), causes the transport to wait for the response to the QUIT
         msg.setText(message, "utf-8");
         msg.setSentDate(new Date());
 
+        SMTPTransport t = (SMTPTransport)session.getTransport(useSSL ? "smtps" : "smtp");
 
-        SMTPTransport t = (SMTPTransport)session.getTransport("smtp");
-        if (useSSL)
-            t = (SMTPTransport)session.getTransport("smtps");
+        if(useSSL || hasPwd) {
+            t.connect(userPrefs.getOutgoingMailServer(), userPrefs.getSmtpUsername(), userPrefs.getSmtpPassword());
+        } else {
+            t.connect();
+        }
 
-        t.connect(userPrefs.getOutgoingMailServer(), userPrefs.getSmtpUsername(), userPrefs.getSmtpPassword());
         t.sendMessage(msg, msg.getAllRecipients());
         t.close();
     }