diff --git a/src/calibre/gui2/wizard/send_email.py b/src/calibre/gui2/wizard/send_email.py
index c0830ddae4..20e73fabe2 100644
--- a/src/calibre/gui2/wizard/send_email.py
+++ b/src/calibre/gui2/wizard/send_email.py
@@ -73,7 +73,7 @@ class SendEmail(QWidget, Ui_Form):
         if opts.relay_password:
             self.relay_password.setText(unhexlify(opts.relay_password))
         self.relay_password.textChanged.connect(self.changed)
-        (self.relay_tls if opts.encryption == 'TLS' else self.relay_ssl).setChecked(True)
+        getattr(self, 'relay_'+opts.encryption.lower()).setChecked(True)
         self.relay_tls.toggled.connect(self.changed)
 
         for x in ('gmail', 'hotmail'):
@@ -210,7 +210,8 @@ class SendEmail(QWidget, Ui_Form):
         conf.set('relay_port', self.relay_port.value())
         conf.set('relay_username', username if username else None)
         conf.set('relay_password', hexlify(password))
-        conf.set('encryption', 'TLS' if self.relay_tls.isChecked() else 'SSL')
+        conf.set('encryption', 'TLS' if self.relay_tls.isChecked() else 'SSL'
+                if self.relay_ssl.isChecked() else 'NONE')
         return True
 
 
diff --git a/src/calibre/gui2/wizard/send_email.ui b/src/calibre/gui2/wizard/send_email.ui
index ba6b6866e2..fbb9500661 100644
--- a/src/calibre/gui2/wizard/send_email.ui
+++ b/src/calibre/gui2/wizard/send_email.ui
@@ -168,7 +168,7 @@
         </property>
        </widget>
       </item>
-      <item row="4" column="2" colspan="2">
+      <item row="4" column="2">
        <widget class="QRadioButton" name="relay_ssl">
         <property name="toolTip">
          <string>Use SSL encryption when connecting to the mail server.</string>
@@ -191,6 +191,16 @@
         </property>
        </spacer>
       </item>
+      <item row="4" column="3">
+       <widget class="QRadioButton" name="relay_none">
+        <property name="toolTip">
+         <string>WARNING: Using no encryption is highly insecure</string>
+        </property>
+        <property name="text">
+         <string>&amp;None</string>
+        </property>
+       </widget>
+      </item>
      </layout>
     </widget>
    </item>
diff --git a/src/calibre/utils/smtp.py b/src/calibre/utils/smtp.py
index 69d790177f..744021f911 100644
--- a/src/calibre/utils/smtp.py
+++ b/src/calibre/utils/smtp.py
@@ -90,7 +90,7 @@ def sendmail(msg, from_, to, localhost=None, verbose=0, timeout=None,
         for x in to:
             return sendmail_direct(from_, x, msg, timeout, localhost, verbose)
     import calibre.utils.smtplib as smtplib
-    cls = smtplib.SMTP if encryption == 'TLS' else smtplib.SMTP_SSL
+    cls = smtplib.SMTP_SSL if encryption == 'SSL' else smtplib.SMTP
     timeout = None # Non-blocking sockets sometimes don't work
     port = int(port)
     kwargs = dict(timeout=timeout, local_hostname=localhost)
@@ -99,7 +99,7 @@ def sendmail(msg, from_, to, localhost=None, verbose=0, timeout=None,
     s = cls(**kwargs)
     s.set_debuglevel(verbose)
     if port < 0:
-        port = 25 if encryption == 'TLS' else 465
+        port = 25 if encryption != 'SSL' else 465
     s.connect(relay, port)
     if encryption == 'TLS':
         s.starttls()
@@ -158,9 +158,9 @@ def option_parser():
     r('-u', '--username', help='Username for relay')
     r('-p', '--password', help='Password for relay')
     r('-e', '--encryption-method', default='TLS',
-      choices=['TLS', 'SSL'],
+      choices=['TLS', 'SSL', 'NONE'],
       help='Encryption method to use when connecting to relay. Choices are '
-      'TLS and SSL. Default is TLS.')
+      'TLS, SSL and NONE. Default is TLS. WARNING: Choosing NONE is highly insecure')
     parser.add_option('-o', '--outbox', help='Path to maildir folder to store '
                       'failed email messages in.')
     parser.add_option('-f', '--fork', default=False, action='store_true',
@@ -231,6 +231,7 @@ def main(args=sys.argv):
     if opts.fork:
         if os.fork() != 0:
             return 0
+
     try:
         sendmail(msg, efrom, eto, localhost=opts.localhost, verbose=opts.verbose,
              timeout=opts.timeout, relay=opts.relay, username=opts.username,