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Sending Emails through Django - WinError 10060 A connection attempt failed and GetAddrInfo Error

I've been running an instance of Django on Windows R2 2012 for over a year and I've come to a road block. Yesterday something happened, I don't know what it could be. The same two errors keep popping up at different times though when trying to send an email:
[WinError 10060] A connection attempt failed because the connected
party did not properly respond after a period of time, or established
connection failed because connected host has failed to respond
and
socket.gaierror: [Errno 11001] getaddrinfo failed
Users are able to connect to the IP address of the server and the port Django is running on 192.168.1.5:8000, but they cannot send emails anymore. Though a percentage do go through as described here, but very few.
Things I've tried
1) This solution
import socket
socket.getaddrinfo('localhost', 8000)
Since I'm doing python manage.py runserver 192.168.1.5:8000, I added that IP and nothing.
2) I went into the Firewall settings and made sure that the ports were all good. The SMTP one that is declared in the setting.py file in my Django project and 25. All of them, inbound and out.
3) I tried sending things on my local machine and it does work. I used other programs that do not use Django to send emails and they do process on all other machines except the Server. So I know it's not my email server.
4) I changed the email config to use my Gmail account and it does process on all other machines except for the server. So it has to be the environment.
5) Editing http_proxy environment variables
The problem, in my case, was that some install at some point defined
an
environment variable http_proxy on my machine when I had no proxy.
Removing the http_proxy environment variable fixed the problem.
As described here
and in my Django project in the wsgi.y file:
os.environ['http_proxy'] = "http://192.168.1.5:8080"
os.environ['https_proxy'] = "http://192.168.1.5:8080"
6) Given this answer here (can someone please explain how I would do it to a django email function), I've also tried this method of wrapping it from solutions here
import smtplib
import socks
#socks.setdefaultproxy(TYPE, ADDR, PORT)
socks.setdefaultproxy(socks.SOCKS5, '192.168.1.5', 8080)
socks.wrapmodule(smtplib)
smtpserver = 'smtp.live.com'
AUTHREQUIRED = 1
smtpuser = 'example#hotmail.fr'
smtppass = 'mypassword'
RECIPIENTS = 'mailto#gmail.com'
SENDER = 'example#hotmail.fr'
mssg = "test message"
s = mssg
server = smtplib.SMTP(smtpserver,587)
server.ehlo()
server.starttls()
server.ehlo()
server.login(smtpuser,smtppass)
server.set_debuglevel(1)
server.sendmail(SENDER, [RECIPIENTS], s)
server.quit()
Though I wouldn't like to use such a method as I'd prefer using Django's built in email service.

Since you have not changed the code and errors you shared shows that it's a network related problem.
It's most probably a DNS issue. In your settings.py you have specified the EMAIL_HOST, which is i believe a hostname. You need to check you server's DNS server.
You are mentioning about checking your firewall settings but what you are doing wrong is not checking the actual connection.
To address the problem you can use couple of command line utilities like telnet or nslookup. You can check if you can resolve a hostname:
nslookup smptp.mail_host.com
This command will fail most probably.
I would like to point what you did wrong in your steps:
1) You have tried to get your services getaddrinfo in which you needed to put your smtp servers hostname, which would result with the same error. Sockets are the very primitive part of the connection on the application layer, you don't really need to dig in to that.
2) Checking firewall settings is OK.
3) This is a good step which shows that there is a problem with your servers network connection.
4) That is another evidence :)
5) You have got it wrong, if you have a proxy server on your network to connect external networks, than you use this settings. But you have configured it wrong. You should not set your projects url as proxy server.
6) This is another deep level coding. You should not use such low level script, which will cause you numerious problems, which would have been handled in high level modules.

I focused my answer on the strange fact that you can get around the problem using a SOCKS5 proxy. (I believe you. There was no time to ask you for details.) You verified that your example solution by SOCKS5 works for you. Django uses the same smtplib and you can easily wrap it the same way by this code added to wsgi.py.
import smtplib
import socks # it is the package SocksiPy or PySocks
socks.setdefaultproxy(socks.SOCKS5, '192.168.1.5', 8080)
socks.wrapmodule(smtplib)
Http(s) proxy (paragraph 5)) is not related because it does not affect SMTP and other protocols except http(s) because "SOCKS operates at a lower level than HTTP proxying".

Connect to .onion websites on tor using python?

Here is the code that i have till now
import socks
import socket
import requests
import json
socks.setdefaultproxy(proxy_type=socks.PROXY_TYPE_SOCKS5, addr="127.0.0.1", port=9050)
socket.socket = socks.socksocket
data = json.loads(requests.get("http://freegeoip.net/json/").text)
and it works fine. The problem is when i use a .onion url it shows error
Failed to establish a new connection: [Errno -2] Name or service not known
After researching a little i found that although the http request is made over tor the resolution still occours over clearnet. What is the proper way so i can also have the domain resolved over tor network to connect to .onion urls ?

Try to avoid the monkey patching if possible. If you're using modern version of requests, then you should have this functionality already.
import requests
import json
proxies = {
'http': 'socks5h://127.0.0.1:9050',
'https': 'socks5h://127.0.0.1:9050'
}
data = requests.get("http://altaddresswcxlld.onion",proxies=proxies).text
print(data)
It's important to specify the proxies using the socks5h:// scheme so that DNS resolution is handled over SOCKS so Tor can resolve the .onion address properly.

There is a more simple solution for this, but therefore you will need Kali Linux. If you have this OS, you can install tor service and kalitorify, start tor service with: sudo service tor start and start kalitorify with sudo kalitorify -t. Now your trafic will be send through tor and you can access .onion sites just as they would be normal sites.

Tor + Urllib2 Python

I am trying to use tor to get a new IP every time I access a website:
import socks
import socket
socks.setdefaultproxy(socks.PROXY_TYPE_SOCKS4, '127.0.0.1', 9151, True)
socket.socket = socks.socksocket
import urllib2
print urllib2.urlopen("http://almien.co.uk/m/tools/net/ip/").read()
I have also tried port 9150, 9050 too.
I keep getting:
socks.ProxyConnectionError: Error connecting to SOCKS4 proxy 127.0.0.1:9151: [Errno 61] Connection refused

Use stem package to interact with Tor. Official site have many tutorials for different cases, for example:
https://stem.torproject.org/tutorials/to_russia_with_love.html

Using SocksiPy with SSL

I'm trying to use SocksIPy with ssl module (from stdlib) to grab a site's remote certificate but SocksIPy won't play with ssl.
The below code will connect to check.torproject.org and state we are not using Tor (meaning SocksIPy is not working) (bad).
Not sure if SocksIPy is the best solution for this but I haven't been able to find any other way to proxify a raw socket (or get pycurl/urllib2 to use SOCKS proxies and give SSL certs!).
To clarify, my issue is that the socket is not being proxied. I'd like to get the ssl certificate with a proxy of my choosing, that's not happening.
Seems right now, I can either have proxy or SSL but not both. Help!
import socks
import ssl
s = socks.socksocket()
s.setproxy(socks.PROXY_TYPE_SOCKS5, "127.0.0.1", 9050)
ss = ssl.wrap_socket(s)
ss.connect(('check.torproject.org', 443))
ss.write("""GET / HTTP/1.0\r
Host: check.torproject.org\r\n\r\n""")
# print ss.getpeercert()
print ss.read(), ss.read(), ss.read()
ss.close()

I have tested this code while running tcpdump so it should work.
import socks
import ssl
s = socks.socksocket()
s.setproxy(socks.PROXY_TYPE_SOCKS5,"127.0.0.1",port=9050)
s.connect(('83.94.121.246', 443))
ss = ssl.wrap_socket(s)
print ss.send("hello")
ss.close()
I didn't review the ssl.py but I guess you have to call connect on the socks object and not the ssl object.

Put ssl.wrap_socket below connect. It doesn't work properly otherwise.
Use validation and CA certfile Getting the certificate from the server requires creating the SSL object with validation turned on and giving it a CA certificates file. If you can't find one on your system you could download the one provided by the CURL project based on Mozilla's as a local file: http://curl.haxx.se/docs/caextract.html
Note: the SocksIPy project hasn't been updated in quite a while and doesn't support Python 3.
Fixed version of original code:
import socks
import ssl
s = socks.socksocket()
s.setproxy(socks.PROXY_TYPE_SOCKS5, "127.0.0.1", port=9050)
s.connect(('check.torproject.org', 443))
ss = ssl.wrap_socket(s, cert_reqs=ssl.CERT_REQUIRED, ca_certs="cacert.pem")
print "Peer cert: ", ss.getpeercert()
ss.write("""GET / HTTP/1.0\r\nHost: check.torproject.org\r\n\r\n""")
content = []
while True:
data = ss.read()
if not data: break
content.append(data)
ss.close()
content = "".join(content)
assert "This browser is configured to use Tor" in content

Python urllib2 Tor 514 Authentication Required

I am trying to use Tor with python and urllib2 and am stuck. The following
print opener.open('http://check.torproject.org/').read()
And
telnet 127.0.0.1 9051
gives me the following error:
514 Authentication Required.
Here is the code I want to use: But I receive the same 514 Authentication Error on the urllib2.urlopen call.
import urllib2
# using TOR !
proxy_support = urllib2.ProxyHandler({"http" : "127.0.0.1:9051"} )
opener = urllib2.build_opener(proxy_support)
urllib2.install_opener(opener)
# every urlopen connection will then use the TOR proxy like this one :
urllib2.urlopen('http://www.google.com').read()
Any suggestions on why this is occurring?
The Tor Vidalia browser -> settings -> Advanced: Authentication set to 'Randomly Generate'
I am Using Python 2.65 urllib2 Tor

Google search suggests (and Tor manual confirms) that 9051 is Tor's default control port. Actual proxy is running on port 9050 by default, which is the one you need to use. However, Vidalia does not use the default ports without extra configuration.
The other problem is that urllib2 is by default unable to work with SOCKS proxies. For possible solutions see these two questions.