diff --git a/src/calibre/gui2/actions/device.py b/src/calibre/gui2/actions/device.py
index d978f9723f..92fc34b105 100644
--- a/src/calibre/gui2/actions/device.py
+++ b/src/calibre/gui2/actions/device.py
@@ -237,20 +237,28 @@ class ConnectShareAction(InterfaceAction):
             self.share_conn_menu.hide_smartdevice_menus()
 
     def set_smartdevice_action_state(self):
-        from calibre.utils.mdns import get_external_ip
+        from calibre.gui2.dialogs.smartdevice import get_all_ip_addresses
         dm = self.gui.device_manager
 
+        all_ips = get_all_ip_addresses()
+        if len(all_ips) > 3:
+            formatted_addresses = _('Many IP addresses. See Start/Stop dialog.')
+            show_port = False
+        else:
+            formatted_addresses = ' or '.join(get_all_ip_addresses())
+            show_port = True
+
         running = dm.is_running('smartdevice')
         if not running:
             text = self.share_conn_menu.DEVICE_MSGS[0]
         else:
             use_fixed_port = dm.get_option('smartdevice', 'use_fixed_port')
             port_number = dm.get_option('smartdevice', 'port_number')
-            if use_fixed_port:
+            if show_port and use_fixed_port:
                 text = self.share_conn_menu.DEVICE_MSGS[1]  + ' [%s port %s]'%(
-                                            get_external_ip(), port_number)
+                                            formatted_addresses, port_number)
             else:
-                text = self.share_conn_menu.DEVICE_MSGS[1]  + ' [%s]'%get_external_ip()
+                text = self.share_conn_menu.DEVICE_MSGS[1] + ' [' + formatted_addresses + ']'
 
         icon = 'green' if running else 'red'
         ac = self.share_conn_menu.control_smartdevice_action
diff --git a/src/calibre/gui2/dialogs/smartdevice.py b/src/calibre/gui2/dialogs/smartdevice.py
index ea4f6741aa..e3028cb6e1 100644
--- a/src/calibre/gui2/dialogs/smartdevice.py
+++ b/src/calibre/gui2/dialogs/smartdevice.py
@@ -5,12 +5,47 @@ from __future__ import (unicode_literals, division, absolute_import,
 __license__   = 'GPL v3'
 __copyright__ = '2008, Kovid Goyal <kovid at kovidgoyal.net>'
 
+import netifaces, socket
+
 from PyQt4.Qt import (QDialog, QLineEdit, Qt)
 
 from calibre.gui2 import error_dialog
 from calibre.gui2.dialogs.smartdevice_ui import Ui_Dialog
 from calibre.utils.config import prefs
 
+def _cmp_ipaddr(l, r):
+    lparts = ['%3s'%x for x in l.split('.')]
+    rparts = ['%3s'%x for x in r.split('.')]
+
+    if lparts[0] in ['192', '170', ' 10']:
+        if rparts[0] not in ['192', '170', '10']:
+            return -1
+        return cmp(rparts, lparts)
+
+    if rparts[0] in ['192', '170', ' 10']:
+        return 1
+
+    return cmp(lparts, rparts)
+
+def get_all_ip_addresses():
+        ip_info = [netifaces.ifaddresses(x).get(netifaces.AF_INET, None)
+                   for x in netifaces.interfaces()]
+
+        all_ipaddrs = list()
+        for iface in ip_info:
+            if iface is not None:
+                for addrs in iface:
+                    if 'netmask' in addrs and addrs['addr'] != '127.0.0.1':
+                        # We get VPN interfaces that were connected and then
+                        # disconnected. Oh well. At least the 'right' IP addr
+                        # is there.
+                        all_ipaddrs.append(addrs['addr'])
+
+        all_ipaddrs.sort(cmp=_cmp_ipaddr)
+        print(all_ipaddrs)
+        return all_ipaddrs
+
+
 class SmartdeviceDialog(QDialog, Ui_Dialog):
 
     def __init__(self, parent):
@@ -49,6 +84,15 @@ class SmartdeviceDialog(QDialog, Ui_Dialog):
               'choice at Preferences -> Send to device -> Metadata management')
                                                     + '</p>')
 
+        self.ip_addresses.setToolTip('<p>' +
+            _('These are the IP addresses detected by calibre for the computer '
+              'running calibre. If you decide to have your device connect to '
+              'calibre using a fixed IP address, one of these addresses should '
+              'be the one you use. It is unlikely but possible that the correct '
+              'IP address is not listed here, in which case you will need to go '
+              "to your computer's control panel to get a complete list of "
+              "your computer's network interfaces and IP addresses.") + '</p>')
+
         self.show_password.stateChanged[int].connect(self.toggle_password)
         self.use_fixed_port.stateChanged[int].connect(self.use_fixed_port_changed)
 
@@ -79,6 +123,8 @@ class SmartdeviceDialog(QDialog, Ui_Dialog):
             self.enable_auto_management_box.setEnabled(False)
             self.auto_management_is_set = True
 
+        self.ip_addresses.setText(', '.join(get_all_ip_addresses()))
+
         self.resize(self.sizeHint())
 
     def use_fixed_port_changed(self, state):
diff --git a/src/calibre/gui2/dialogs/smartdevice.ui b/src/calibre/gui2/dialogs/smartdevice.ui
index fadcf921b4..a8cd546aff 100644
--- a/src/calibre/gui2/dialogs/smartdevice.ui
+++ b/src/calibre/gui2/dialogs/smartdevice.ui
@@ -38,7 +38,34 @@
      </property>
     </widget>
    </item>
+   <item row="1" column="0">
+    <widget class="QLabel" name="label_23">
+     <property name="text">
+      <string>Calibre's IP addresses:</string>
+     </property>
+    </widget>
+   </item>
    <item row="1" column="1">
+    <widget class="QLabel" name="ip_addresses">
+     <property name="text">
+      <string>Possibe IP addresses:</string>
+     </property>
+     <property name="wordWrap">
+      <bool>true</bool>
+     </property>
+    </widget>
+   </item>
+   <item row="2" column="0">
+    <widget class="QLabel" name="label_2">
+     <property name="text">
+      <string>Optional &amp;password:</string>
+     </property>
+     <property name="buddy">
+      <cstring>password_box</cstring>
+     </property>
+    </widget>
+   </item>
+   <item row="2" column="1">
     <widget class="QLineEdit" name="password_box">
      <property name="sizePolicy">
       <sizepolicy hsizetype="Expanding" vsizetype="Expanding">
@@ -54,24 +81,14 @@
      </property>
     </widget>
    </item>
-   <item row="1" column="0">
-    <widget class="QLabel" name="label_2">
-     <property name="text">
-      <string>Optional &amp;password:</string>
-     </property>
-     <property name="buddy">
-      <cstring>password_box</cstring>
-     </property>
-    </widget>
-   </item>
-   <item row="1" column="2">
+   <item row="2" column="2">
     <widget class="QCheckBox" name="show_password">
      <property name="text">
       <string>&amp;Show password</string>
      </property>
     </widget>
    </item>
-   <item row="2" column="0">
+   <item row="4" column="0">
     <widget class="QLabel" name="label_21">
      <property name="text">
       <string>Optional &amp;fixed port:</string>
@@ -81,7 +98,7 @@
      </property>
     </widget>
    </item>
-   <item row="2" column="1">
+   <item row="4" column="1">
     <widget class="QLineEdit" name="fixed_port">
      <property name="sizePolicy">
       <sizepolicy hsizetype="Expanding" vsizetype="Expanding">
@@ -94,28 +111,28 @@
      </property>
     </widget>
    </item>
-   <item row="2" column="2">
+   <item row="4" column="2">
     <widget class="QCheckBox" name="use_fixed_port">
      <property name="text">
       <string>&amp;Use a fixed port</string>
      </property>
     </widget>
    </item>
-   <item row="3" column="0" colspan="3">
+   <item row="6" column="0" colspan="3">
     <widget class="QCheckBox" name="autostart_box">
      <property name="text">
       <string>&amp;Automatically allow connections at calibre startup</string>
      </property>
     </widget>
    </item>
-   <item row="4" column="0" colspan="3">
+   <item row="8" column="0" colspan="3">
     <widget class="QCheckBox" name="enable_auto_management_box">
      <property name="text">
       <string>&amp;Enable automatic sending of book metadata when your device connects</string>
      </property>
     </widget>
    </item>
-   <item row="5" column="0" colspan="3">
+   <item row="10" column="0" colspan="3">
     <widget class="QDialogButtonBox" name="buttonBox">
      <property name="orientation">
       <enum>Qt::Horizontal</enum>