diff --git a/onionshare/onionshare.py b/onionshare/onionshare.py
index f102133f..998753bf 100644
--- a/onionshare/onionshare.py
+++ b/onionshare/onionshare.py
@@ -11,6 +11,8 @@ class TailsError(Exception): pass
 
 class OnionShare(object):
     def __init__(self, debug=False, local_only=False, stay_open=False):
+        self.port = None
+
         # debug mode
         if debug:
             web.debug_mode()
@@ -24,10 +26,6 @@ class OnionShare(object):
         # files and dirs to delete on shutdown
         self.cleanup_filenames = []
 
-        # choose a random port
-        self.choose_port()
-        self.local_host = "127.0.0.1:{0}".format(self.port)
-
     def cleanup(self):
         for filename in self.cleanup_filenames:
             if os.path.isfile(filename):
@@ -44,6 +42,9 @@ class OnionShare(object):
         tmpsock.close()
 
     def start_hidden_service(self, gui=False, tails_root=False):
+        if not self.port:
+            self.choose_port()
+
         if helpers.get_platform() == 'Tails' and not tails_root:
             # in Tails, start the hidden service in a root process
             if gui:
@@ -115,9 +116,15 @@ class OnionShare(object):
                 ready = True
 
                 sys.stdout.write('{0}\n'.format(strings._('wait_for_hs_yup')))
-            except:
+            except TypeError: # non-Tails error
                 sys.stdout.write('{0}\n'.format(strings._('wait_for_hs_nope')))
                 sys.stdout.flush()
+            except urllib2.HTTPError: # Tails error
+                sys.stdout.write('{0}\n'.format(strings._('wait_for_hs_nope')))
+                sys.stdout.flush()
+            except KeyboardInterrupt:
+                return False
+        return True
 
 def tails_root():
     # if running in Tails and as root, do only the things that require root
@@ -137,6 +144,7 @@ def tails_root():
 
         # start hidden service
         app = OnionShare()
+        app.choose_port()
         app.port = port
         app.start_hidden_service(False, True)
         sys.stdout.write(app.onion_host)
@@ -186,6 +194,7 @@ def main():
     # start the onionshare app
     try:
         app = OnionShare(debug, local_only, stay_open)
+        app.choose_port()
         print strings._("connecting_ctrlport").format(app.port)
         app.start_hidden_service()
     except NoTor as e:
@@ -204,7 +213,10 @@ def main():
     t.start()
 
     # wait for hs
-    app.wait_for_hs()
+    ready = app.wait_for_hs()
+    if not ready:
+        sys.exit()
+
     print strings._("give_this_url")
     print 'http://{0}/{1}'.format(app.onion_host, web.slug)
     print ''
diff --git a/onionshare/web.py b/onionshare/web.py
index c7363c58..501e8dac 100644
--- a/onionshare/web.py
+++ b/onionshare/web.py
@@ -179,6 +179,14 @@ def start(port, stay_open=False):
 def stop():
     # to stop flask, load http://127.0.0.1:<port>/<shutdown_slug>/shutdown
     try:
-        urllib2.urlopen('http://127.0.0.1:{0}/{1}/shutdown'.format(app.port, shutdown_slug)).read()
+        if helpers.get_platform() == 'Tails':
+            # in Tails everything is proxies over Tor, so we need to get lower level
+            # to connect not over the proxy
+            import socket
+            s = socket.socket()
+            s.connect(('127.0.0.1', app.port))
+            s.sendall('GET /{0}/shutdown HTTP/1.1\r\n\r\n'.format(shutdown_slug))
+        else:
+            urllib2.urlopen('http://127.0.0.1:{0}/{1}/shutdown'.format(app.port, shutdown_slug)).read()
     except:
         pass
diff --git a/onionshare_gui/onionshare_gui.py b/onionshare_gui/onionshare_gui.py
index 8e2b8270..5ef29180 100644
--- a/onionshare_gui/onionshare_gui.py
+++ b/onionshare_gui/onionshare_gui.py
@@ -83,6 +83,7 @@ class OnionShareGui(QtGui.QWidget):
         # start the hidden service
         self.status_bar.showMessage(strings._('gui_starting_server').format(self.app.port))
         try:
+            self.app.choose_port()
             print strings._("connecting_ctrlport").format(self.app.port)
             self.app.start_hidden_service(gui=True)
         except onionshare.NoTor as e: