dev_appserver.py --smtp_host=smtp.gmail.com --smtp_port=25 --smtp_user=xxx@gmail.com--smtp_password=k1tt3ns myapp

Traceback (most recent call last):
  File "C:Program FilesGooglegoogle_appenginegoogleappengineextwebapp__init__.py", line 500, in __call__
    handler.post(*groups)
  File "C:Documents and SettingsdeskDesktopappstempmain.py", line 139, in post
    """)
  File "C:Program FilesGooglegoogle_appenginegoogleappengineapimail.py", line 205, in send_mail
    message.send(make_sync_call)
  File "C:Program FilesGooglegoogle_appenginegoogleappengineapimail.py", line 474, in send
    make_sync_call('mail', self._API_CALL, message, response)
  File "C:Program FilesGooglegoogle_appenginegoogleappengineapiapiproxy_stub_map.py", line 68, in MakeSyncCall
    apiproxy.MakeSyncCall(service, call, request, response)
  File "C:Program FilesGooglegoogle_appenginegoogleappengineapiapiproxy_stub_map.py", line 240, in MakeSyncCall
    stub.MakeSyncCall(service, call, request, response)
  File "C:Program FilesGooglegoogle_appenginegoogleappengineapiapiproxy_stub.py", line 80, in MakeSyncCall
    method(request, response)
  File "C:Program FilesGooglegoogle_appenginegoogleappengineapimail_stub.py", line 203, in _Send
    self._SendSMTP(mime_message, smtp_lib)
  File "C:Program FilesGooglegoogle_appenginegoogleappengineapimail_stub.py", line 133, in _SendSMTP
    smtp.login(self._smtp_user, self._smtp_password)
  File "C:Python26libsmtplib.py", line 552, in login
    raise SMTPException("SMTP AUTH extension not supported by server.")
SMTPException: SMTP AUTH extension not supported by server.

# After smtp.connect(self._smtp_host, self._smtp_port)
smtp.ehlo()
smtp.starttls()
smtp.ehlo()

find / -name "mail_stub.py" -type f 2>/dev/null

/Applications/GoogleAppEngineLauncher.app/Contents/Resources/GoogleAppEngine-default.bundle/Contents/Resources/google_appengine/google/appengine/api/mail_stub.py

if self._allow_tls and smtp.has_extn ('STARTTLS'):
  smtp.starttls ()

dev_appserver.py --smtp_host=smtp.gmail.com --smtp_port=25 --smtp_user=xxx@gmail.com --smtp_password=yyy myapp