Django configuration to send email on server - python

I really need your help. About a week I'm trying to configure mail on my server. I use nginx -> uwsgi -> django application.
The problem is that the mail server works only with the following backend:
class SSLEmailBackend(EmailBackend):
def open(self):
if self.connection:
return False
try:
self.connection = smtplib.SMTP_SSL(
self.host, self.port, local_hostname=DNS_NAME.get_fqdn())
if self.username and self.password:
self.connection.ehlo()
# Remove CRAM-MD5 authentication method
self.connection.esmtp_features['auth'] = 'PLAIN LOGIN'
self.connection.login(self.username, self.password)
return True
except:
if not self.fail_silently:
raise
My settings for it:
EMAIL_BACKEND = "my_app.backends.SSLEmailBackend"
EMAIL_HOST = "mail.my_mail_server.com"
EMAIL_PORT = 465
EMAIL_HOST_USER = "host#myhost.com"
EMAIL_HOST_PASSWORD = "my_pass"
DEFAULT_FROM_EMAIL = "host#myhost.com"
Locally, it works completely well!
The strangest thing that a message can be sent without any errors in the server console:
>> from django.core.mail import send_mail
>> send_mail('test email', 'hello world', '', ['my_test#gmail.com'])
The problem comes when I try to register a new user. I use Django-userena backend for registration. Registration is successful, but the emails come only on the server to /var/mail/user1
Text of email:
rom MAILER-DAEMON Sun Oct 26 02:06:01 2014
Return-path: <>
Envelope-to: webmaster#localhost
Delivery-date: Sun, 26 Oct 2014 02:06:01 +0400
Received: from Debian-exim by mail.my_mail_server.com with local (Exim 4.80)
id 1Xi9TF-0002Wp-Ml
for webmaster#localhost; Sun, 26 Oct 2014 02:06:01 +0400
X-Failed-Recipients: test#test.com
Auto-Submitted: auto-replied
From: Mail Delivery System <Mailer-Daemon#elib.rshu.ru>
To: webmaster#localhost
Subject: Mail delivery failed: returning message to sender
Message-Id: <E1Xi9TF-0002Wp-Ml#mail.my_mail_server.com>
Date: Sun, 26 Oct 2014 02:06:01 +0400
Status: O
This message was created automatically by mail delivery software.
A message that you sent could not be delivered to one or more of its
recipients. This is a permanent error. The following address(es) failed:
test#test.com
Mailing to remote domains not supported
------ This is a copy of the message, including all the headers. ------
Return-path: <webmaster#localhost>
Received: from localhost ([::1] helo=mail.my_mail_server.com)
by mail.my_mail_server.com with esmtp (Exim 4.80)
(envelope-from <webmaster#localhost>)
id 1Xi9TF-0002Wm-Lv
for test#test.com; Sun, 26 Oct 2014 02:06:01 +0400
MIME-Version: 1.0
Content-Type: text/plain; charset="utf-8"
Content-Transfer-Encoding: 8bit
Subject: =?utf-8?b?0KDQtdCz0LjRgdGC0YDQsNGG0LjRjyDQsiDRjdC70LXQutGC0YDQvtC90L0=?=
=?utf-8?b?0L7QuSDQsdC40LHQu9C40L7RgtC10LrQtSDQoNCT0JPQnNCj?=
From: webmaster#localhost
To: test#test.com
Date: Sat, 25 Oct 2014 22:06:01 -0000
....
I've been checking userena, nginx, etc. I can not understand what could be the problem. Why it works locally and on the server console messages can be sent. Please help.

Your mail server is not set up to accept remote mail forwarding. The error message from the server is 'Mailing to remote domains not supported.' So, whatever mail server you are connecting to is not recognizing that your web server is a 'trusted user' who's mail should be accepted and forwarded. I would try to get your mail service provider to whitelist your server for sending email.

Related

connect to gmail in python via imaplib

I have a python script that downloads daily attachments from a specific email address from gmail.
Everything works great locally. The problem occurs when I try to upload it to the server.
Code below:
import email
import os
import imaplib
import socket
def download_attachments():
print('Connect with IMAP')
imap_server = imaplib.IMAP4_SSL('imap.gmail.com')
print('Login details')
username = "email#gmail.com"
password = "password"
print('Login to mail')
try:
imap_server.login(username, password)
except imaplib.IMAP4.error as error:
return (f'Error while login: {error}')
after running the code on the server, it shows me in the console
Connect with IMAP
and nothing else happens.
Server details
Production Python scripts server.
Updated : Sat 14 Jan 2023 02:55:01 PM CET Hostname
: xxxxxxx IP address : xxxxxxx System type : Debian
GNU/Linux 11 (bullseye) Load : 0.02 0.06 0.07 1/114
59615 HW resources : 2 CPU | 3931 MB RAM
debug2: client_check_window_change: changed debug2: channel 0: request
window-change confirm 0 debug3: send packet: type 98 Last login: Sat
Jan 14 14:19:25 2023 from xxxxxxx This system is managed by Ansible,
all local changes will be lost.
Production Python scripts server.
Updated : Sat 14 Jan 2023 02:55:01 PM CET Hostname
: xxxxxxx IP address : xxxxxxx System type : Debian
GNU/Linux 11 (bullseye) Load : 0.02 0.06 0.07 1/114
59615 HW resources : 2 CPU | 3931 MB RAM

bad request socket python

I'm using socket to build a simple "web browser" but I'm getting stuck at the start, whit a bad request result, here is my code:
import socket
mysocket = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
URI = 'data.pr4e.org'
mysocket.connect((URI, 80))
cmd = "GET http://{0}/romeo.txt HTTP/1.0\n\n".format(URI).encode()
mysocket.send(cmd) # send a request
while True:
data = mysocket.recv(512) # recieve 512 bites at time
# if there is no more information to recive, then, close the loop
if (len(data) < 1):
break
print(data.decode())
pass
mysocket.close() # close connection
here is the output
HTTP/1.1 400 Bad Request
Date: Mon, 15 Feb 2021 14:36:06 GMT
Server: Apache/2.4.18 (Ubuntu)
Content-Length: 308
Connection: close
Content-Type: text/html; charset=iso-8859-1
<!DOCTYPE HTML PUBLIC "-//IETF//DTD HTML 2.0//EN">
<html><head>
<title>400 Bad Request</title>
</head><body>
<h1>Bad Request</
h1>
<p>Your browser sent a request that this server could not understand.<br />
</p>
<hr>
<address>Apache/2.4.18 (Ubuntu) Server at do1.dr-chuck.com Port 80</address>
what I'm doing wrong? also, I tryed replacing data.pr4e.org by facebook.com and youtube.com and I get this output:
HTTP/1.1 301 Moved Permanently
Vary: Accept-Encoding
Location: https://facebook.com/
Content-Type: text/html; charset="utf-8"
X-FB-Debug: LPmWQm0VVptVpi8QX8/SxymrJg9ZoL/mL+W+G4pZA4HGj5WI5YIG1s8sgqwp6TIleGvUg3U1eDNEhGoCsaJG5g==
Date: Mon, 15 Feb 2021 14:52:43 GMT
Alt-Svc: h3-29=":443"; ma=3600,h3-27=":443"; ma=3600
Connection: close
Content-Length: 0
thank you
Here the problem is just that you used \n when the server expected \r\n for end of line.
Anyway, as you directly connect to the HTTP host, you should not put the full URI in the request line. This would be better on a HTTP 1.0 conformance point:
cmd = "GET /romeo.txt HTTP/1.0\r\n\r\n".encode()
But if the server could accept more that one virtual server, you should pass the name in a Host header:
cmd = "GET /romeo.txt HTTP/1.0\r\nHost: {}\r\n\r\n".format(URI).encode()

Images not showing up in email

EDIT: This issue resolved itself as mysteriously as it began. Simply hoping it doesn't crop up again in the future.
I have a small python script that emails out a comic strip once a day to a handful of email addresses. Recently, one person on my list told me that the images are no longer displayed. I got the source of the email from her Gmail account, and for some reason the base-64 encoded section for the image in blank.
I have no idea why this is happening, and why it's happening to only one person. I get an SPF soft-fail in the Gmail headers, but I doubt that's causing it (that should happen to all the Gmail users on my list.) I don't even know what to Google to start troubleshooting this issue.
Faulty Email Source {censored items in curly braces}:
Delivered-To: {recipient}#gmail.com
Received: by 2002:ac2:555e:0:0:0:0:0 with SMTP id l30csp2647742lfk;
Sun, 22 Mar 2020 02:12:09 -0700 (PDT)
X-Google-Smtp-Source: ADFU+vt1SopHnbnPh0tuHjbA/v3RMASeIKMyk35ZdIXqQHBr2LmtG11vVo6cI8XXxUf/emCJQjqb
X-Received: by 2002:a92:25d6:: with SMTP id l205mr14876228ill.35.1584868329096;
Sun, 22 Mar 2020 02:12:09 -0700 (PDT)
ARC-Seal: i=1; a=rsa-sha256; t=1584868329; cv=none;
d=google.com; s=arc-20160816;
b=o1VVDgxlMMWGRPy041qJS6LfA1LWjEB6+cbp768sLmMaOk7Q+qbCpAg0Mydf3pg/yu
N3Nfh0Zv7vUdS6sapH0LzmcCG6YVBC/fkGboFuUeVJgVw24CcY8e1ofkMmIkWardIQie
bNfAnebSMmIhmZ6UTrR79ggRhUglFx6EdAzNYdmpyRCxewK3/SN5JjdfW6KUQsgjQXU5
PvJQEZZrt07eKjzq2kpNVobWBj8rOvVGpYc+fqNDOircTIF5ZTI3JIbCEkNvvEyAmZOW
AK68xVtSpaYfInnJ0++dPkS9DhuH777f/yMz6Z0X26MjnoxiIovyYSNPfzZLdjpnC/CI
G4nQ==
ARC-Message-Signature: i=1; a=rsa-sha256; c=relaxed/relaxed; d=google.com; s=arc-20160816;
h=date:message-id:to:from:subject:mime-version;
bh=nXPNVg7/Z2G2UDLCbHAibUHl0oCh4sJ6yhHsm9HpP+Y=;
b=Vl5At9J4nLzeREzg93sHypB2XO/vbNHAtRj4apOzQZHLg0XbjD3Hxv6t9+yzFn8thS
pFnPRPCOOgyY+mp+8hTQrT5TaIlEcNC9Ay1x25X27wqcr0iBjw9xpTvjvFo1pX7jNK7E
DvUZpdSoSmas32U0zT8DH1+jX5zX/8Ydr7aTOkVLPX6umVuyl2RNlW+mLZrPnCMkiH0Z
jeTc88LMiczwsVwo2qsoKPDjFah+xTD7J+zqnuHr6IuMS3+s9t7dy4sbKRwlcxP4n2z4
ZXjJbQpEEfOec36EF89By4ZHNHxLmDx/DZvPA5nv10emet1Omki9w2HF3hcaAijZDL2l
jb1g==
ARC-Authentication-Results: i=1; mx.google.com;
spf=softfail (google.com: domain of transitioning {sender}#{my-domain} does not designate {my-ip-address} as permitted sender) smtp.mailfrom={sender}#{my-domain}
Return-Path: <{sender}#{my-domain}>
Received: from {my-domain} ([{my-ip-address}])
by mx.google.com with ESMTP id 141si8443110ile.78.2020.03.22.02.12.03
for <{recipient}#gmail.com>;
Sun, 22 Mar 2020 02:12:09 -0700 (PDT)
Received-SPF: softfail (google.com: domain of transitioning {sender}#{my-domain} does not designate {my-ip-address} as permitted sender) client-ip={my-ip-address};
Authentication-Results: mx.google.com;
spf=softfail (google.com: domain of transitioning {sender}#{my-domain} does not designate {my-ip-address} as permitted sender) smtp.mailfrom={sender}#{my-domain}
Received: from {my-domain} (localhost [IPv6:::1]) by {my-domain} (Postfix) with SMTP id BEFC13C00DD for <{recipient}#gmail.com>; Sun, 22 Mar 2020 05:12:02 -0400 (EDT)
Content-Type: multipart/related; boundary="===============0513549325=="
MIME-Version: 1.0
Subject: Calvin and Hobbes of the day
From: {sender}#{my-domain}
To: {recipient}#gmail.com
Message-Id: <20200322091202.BEFC13C00DD#{my-domain}>
Date: Sun, 22 Mar 2020 05:12:02 -0400 (EDT)
--===============0513549325==
Content-Type: multipart/alternative; boundary="===============1139914447=="
MIME-Version: 1.0
--===============1139914447==
Content-Type: text/plain; charset="us-ascii"
MIME-Version: 1.0
Content-Transfer-Encoding: 7bit
Calvin and Hobbes of the day email. Image not displayed for techical reasons. To unsubscribe, send an email to {sender}#{my-domain} with the subject "Unsubscribe please". You may briefly continue to recieve emails until the system processes your request.
--===============1139914447==
Content-Type: text/html; charset="us-ascii"
MIME-Version: 1.0
Content-Transfer-Encoding: 7bit
<img src="cid:30cbc076bf26fa38547141665a3874fc0bdc91b550d5b9523fbf033cd64d0d8b"><p>This Calvin and Hobbes was originally published on Tuesday, March 22, 1994. Enjoy!</p><p style="font-family:serif;text-size:9pt;">To unsubscribe, send an email to {sender}#{my-domain} with the subject "Unsubscribe please". You may briefly continue to recieve emails until the system processes your request.</p>
--===============1139914447==--
--===============0513549325==
Content-Type: image/gif
MIME-Version: 1.0
Content-Transfer-Encoding: base64
Content-ID: <30cbc076bf26fa38547141665a3874fc0bdc91b550d5b9523fbf033cd64d0d8b>
--===============0513549325==--
Example of an email that displayed properly (also sent to a Gmail account):
Delivered-To: {recipient2}#gmail.com
Received: by 2002:ac0:945c:0:0:0:0:0 with SMTP id j28csp4283482imj;
Sun, 22 Mar 2020 02:12:06 -0700 (PDT)
X-Google-Smtp-Source: ADFU+vsBj6iMIZiI5aEUI+EaVIoyR/pGQUdx46SNDNiosv8OoI8WLTCvAYmWxdVSsUEGEThEY3kc
X-Received: by 2002:a92:4090:: with SMTP id d16mr1882262ill.200.1584868326631;
Sun, 22 Mar 2020 02:12:06 -0700 (PDT)
ARC-Seal: i=1; a=rsa-sha256; t=1584868326; cv=none;
d=google.com; s=arc-20160816;
b=o85d2nyxnlrJBxjPjbEIK+iBEUzip5+8qaw3AP2sf1oWPSHGUjyKSJMM9ya0nTgByo
wn+hN60zGz/y23w7k6yp3V0gy94rP+qiMRn87bgahsdF6SOH6n2gDn1aYPFNZPCLRrgU
UI+a3aX/qdDtw03LL8A9mj+v+TCvEyntddxWjiU2UHuXT88GLOPAwmt0PwH/wQp52nRV
V4jnKFbGQU7A2FkzJccW1T6GgzoXejmXOcHi4z7emm4TGHNv4FxlPl/bna2X8dFo+8N5
mHh7+ADWyy9wHATPJqPEtTXuBoE8Bri9n20IMKaPWKzpoasb5bFV14kA+cRkh/CckHr7
3Vxw==
ARC-Message-Signature: i=1; a=rsa-sha256; c=relaxed/relaxed; d=google.com; s=arc-20160816;
h=date:message-id:to:from:subject:mime-version;
bh=tcCxyEZafImccO+owloPVRqzcCuM+m7me+VxZuISjGU=;
b=e5DjPTX5Ia11uM7bKBRA+vGqkGlsYdJuv6Mxio7xhRtcxqBxxxyIZ80ludnCvWR/j8
/B1qmGG6ZynxVlv7GTPOF4yP6qWhE2sycKf3yQ5MYZXLFmZMRSW0kcj/fjoKvd3BOOBV
8DlZUNVvfNujZpm+7sdNHhT+xAU8EY1+9+b3R6GDEyDJzKrIgXclX9yVHsH91DDa5AC8
WOUBH4ZrOZ0Zn5bvpSLOomqhGI4J2gZeb41zj8RjjuwPOE9LR5fmDCxNn+ajeBAbnJPG
Ihl3jkrnuiJWcigsn38ctPw6inWglsK3dxKBTeXbrWHHeRtu9kHZnL1l9vpl93BM/LN9
6jgQ==
ARC-Authentication-Results: i=1; mx.google.com;
spf=softfail (google.com: domain of transitioning {sender}#{my-domain} does not designate {my-ip-address} as permitted sender) smtp.mailfrom={sender}#{my-domain}
Return-Path: <{sender}#{my-domain}>
Received: from {my-domain} ([{my-ip-address}])
by mx.google.com with ESMTP id k2si9367254jap.23.2020.03.22.02.12.03
for <{recipient2}#gmail.com>;
Sun, 22 Mar 2020 02:12:06 -0700 (PDT)
Received-SPF: softfail (google.com: domain of transitioning {sender}#{my-domain} does not designate {my-ip-address} as permitted sender) client-ip={my-ip-address};
Authentication-Results: mx.google.com;
spf=softfail (google.com: domain of transitioning {sender}#{my-domain} does not designate {my-ip-address} as permitted sender) smtp.mailfrom={sender}#{my-domain}
Received: from {my-domain} (localhost [IPv6:::1])
by {my-domain} (Postfix) with SMTP id 98FA73C00A7
for <{recipient2}#gmail.com>; Sun, 22 Mar 2020 05:12:02 -0400 (EDT)
Content-Type: multipart/related; boundary="===============1535165371=="
MIME-Version: 1.0
Subject: Calvin and Hobbes of the day
From: {sender}#{my-domain}
To: {recipient2}#gmail.com
Message-Id: <20200322091202.98FA73C00A7#{my-domain}>
Date: Sun, 22 Mar 2020 05:12:02 -0400 (EDT)
This is a multi-part message in MIME format.
--===============1535165371==
Content-Type: multipart/alternative; boundary="===============1545014324=="
MIME-Version: 1.0
--===============1545014324==
Content-Type: text/plain; charset="us-ascii"
MIME-Version: 1.0
Content-Transfer-Encoding: 7bit
Calvin and Hobbes of the day email. Image not displayed for techical reasons. To unsubscribe, send an email to {sender}#{my-domain} with the subject "Unsubscribe please". You may briefly continue to recieve emails until the system processes your request.
--===============1545014324==
Content-Type: text/html; charset="us-ascii"
MIME-Version: 1.0
Content-Transfer-Encoding: 7bit
<img src="cid:30cbc076bf26fa38547141665a3874fc0bdc91b550d5b9523fbf033cd64d0d8b"><p>This Calvin and Hobbes was originally published on Tuesday, March 22, 1994. Enjoy!</p><p style="font-family:serif;text-size:9pt;">To unsubscribe, send an email to {sender}#{my-domain} with the subject "Unsubscribe please". You may briefly continue to recieve emails until the system processes your request.</p>
--===============1545014324==--
--===============1535165371==
Content-Type: image/gif
MIME-Version: 1.0
Content-Transfer-Encoding: base64
Content-ID: <30cbc076bf26fa38547141665a3874fc0bdc91b550d5b9523fbf033cd64d0d8b>
R0lGODlhhAMgAfcAAAAAAAEBAQICAgMDAwQEBAUFBQYGBgcHBwgICAkJCQoKCgsLCwwMDA0NDQ4O
Dg8PDxAQEBERERISEhMTExQUFBUVFRYWFhcXFxgYGBkZGRoaGhsbGxwcHB0dHR4eHh8fHyAgICEh
ISIiIiMjIyQkJCUlJSYmJicnJygoKCkpKSoqKisrKywsLC0tLS4uLi8vLzAwMDExMTIyMjMzMzQ0
NDU1NTY2Njc3Nzg4ODk5OTo6Ojs7Ozw8PD09PT4+Pj8/P0BAQEFBQUJCQkNDQ0REREVFRUZGRkdH
R0hISElJSUpKSktLS0xMTE1NTU5OTk9PT1BQUFFRUVJSUlNTU1RUVFVVVVZWVldXV1hYWFlZWVpa
WltbW1xcXF1dXV5eXl9fX2BgYGFhYWJiYmNjY2RkZGVlZWZmZmdnZ2hoaGlpaWpqamtra2xsbG1t
{ ... snipped 1462 lines worth of base-64 encoded data ... }
/pQ29JRRfUNJrQ5VOZVPzEP3CAxVzcM3zIPr2EdJ6dRKDoxUvcND5NIWCVEsBQYYmRMg4UUuKYT9
1FBCrKQ9+MVKGsTwHERX8eRCzEMrVsM3kMMmGhUmro7jxKRBXOU8SFVM8sS4eFA2+eRZomVKBGVK
vMMuRMIglFFatoZUAVEVHMIp9MKzpANRLoQ2DEI3yWVgCuZgEmZhGuZhIuZPRgREDEwS+eRaJmZi
yos5HeUS2ZBjHmWWJBHkJMYObWb8gCYPsc9oro/6EIxN3JD8mM5okiZjFsxicqbpyJBpwolpztBr
OiZqglFWVIVr/lBqpib4uI9uug9nMmZmFuf7dqCmcp6mD2Hmc+oGpwjnZ7LJEhlnD9XmDkXOcl5m
Y/LQb87mdopnbBIRDdlQZaqmdmYndlqQUjind8KncH6nq1SnD6GnbuJnfq5lZVIJZEZmJu1mpKhl
bhLoSrhmbZxTgf7ngjJoutBngy6mbCbFFPknhA5mQAAAOw==
--===============1535165371==--
EDIT: A few of my other recipients have also reported that this has happened in the past, but it only lasted a day or two, and they didn't think much of it. (I believe they are all also Gmail users...)
EDIT: Here's a slightly stripped-down version of the code that sends the emails. There is a file called addresses.py in the same directory that has a nested array with all the email addresses on my list.
#!/usr/bin/python
from email.MIMEMultipart import MIMEMultipart
from email.MIMEText import MIMEText
from email.MIMEImage import MIMEImage
import hashlib
import os
import datetime
from addresses import arrayTo # Addresses to send to
# Note: Calvin and Hobbes ran from 1985-11-18 to 1995-12-31
today = datetime.datetime.now()
comicDay = datetime.datetime(((today.year - 6) % 10 + 1990), today.month, today.day)
dateString = str(comicDay.year) + '-' + str(comicDay.month) + '-' + str(comicDay.day)
# Some definitions
for n in range(0,len(arrayTo)):
strTo = ''
numAddresses = len(arrayTo[n])
for i in range(0,numAddresses): # Concatenate address array into CSV
strTo += arrayTo[n][i]
if i < numAddresses - 1: # Don't end with a comma
strTo += ', '
strFrom = '{sender}#{my-domain}'
comicFile = '/path/to/files/picture_' + dateString + '.png'
if os.path.exists(comicFile):
# Open the image, assuming the image is in the current directory
fp = open(comicFile, 'rb')
msgImage = MIMEImage(fp.read())
fp.close()
# Generate a hash to use as the CID
comicHash = hashlib.sha256(comicFile).hexdigest()
# Create the root message and fill in the from, to, and subject headers
msgRoot = MIMEMultipart('related')
msgRoot['Subject'] = 'Calvin and Hobbes of the day'
msgRoot['From'] = strFrom
msgRoot['To'] = strTo
msgRoot.preamble = 'This is a multi-part message in MIME format.'
# Encapsulate the plain and HTML versions of the message body in an
# 'alternative' part, so message agents can decide which they want to display.
msgAlternative = MIMEMultipart('alternative')
msgRoot.attach(msgAlternative)
msgText = MIMEText('Calvin and Hobbes of the day email. Image not displayed for techical reasons. To unsubscribe, send an email to {sender}#{my-domain} with the subject "Unsubscribe please". You may briefly continue to recieve emails until the system processes your request.')
msgAlternative.attach(msgText)
# We reference the image in the IMG SRC attribute by the ID we chose above
msgText = MIMEText('<img src="cid:' + comicHash + '"><p>This Calvin and Hobbes was originally published on ' + comicDay.strftime('%A, %B %d, %Y') + '. Enjoy!</p><p style="font-family:serif;text-size:9pt;">To unsubscribe, send an email to {sender}#{my-domain} with the subject "Unsubscribe please". You may briefly continue to recieve emails until the system processes your request.</p>', 'html')
msgAlternative.attach(msgText)
# Define the image's ID as referenced above
msgImage.add_header('Content-ID', '<' + comicHash + '>')
msgRoot.attach(msgImage)
# Send the email
import smtplib
smtpObj = smtplib.SMTP('localhost', 25)
smtpObj.helo()
smtpStatus = smtpObj.sendmail(strFrom, arrayTo[n], msgRoot.as_string())
smtpObj.quit()
if (smtpStatus != {}):
# code to log this error
else:
# code to log this error

Email flagged as SPAM with correct authentication

I'm using Python with the framework Django. I am sending registration emails from my website (when a user register).
Using this snippet, I authenticate my email with DKIM (the DNS is correctly configured).
I also added SPF on my DNS.
Either on gmail and hotmail, I see spf=pass and dkim=pass.
But still, my email is flagged as spam. I made sure to use appropriate vocabulary, it's a text email with only 1 link (for registering). I am using no-reply#mydomain.com in FROM field for my email.
EDIT : After few changes I managed to have a "proper" header for my email. This is what it looks like (received on my hotmail account, still flagged as spam) (I replaced my domain name by mydomain.com and IP adress by stars, but they are correct) :
x-store-info:4r51+eLowCe79NzwdU2kRyU+pBy2R9QCQ99fuVSCLVOS47rfbRPiE7iaYhO1ERiggdK+K18l1xsWi4P40pG/T41xqL9zUAoU17o0RrecEQY1EuSFAsrgi0P9JxG/GRiKRWTxOOBRX7E=
Authentication-Results: hotmail.com; spf=pass (sender IP is ***.***.***.***) smtp.mailfrom=no-reply#mydomain.com; dkim=pass header.d=mydomain.com; x-hmca=pass header.id=no-reply#mydomain.com
X-SID-PRA: no-reply#mydomain.com
X-AUTH-Result: PASS
X-SID-Result: PASS
X-Message-Status: n:n
X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0wO0Q9MjtHRD0yO1NDTD02
X-Message-Info: 11chDOWqoTn7F4e7hHYwxaXv9iZKZZyIKj/+21TGh6QZKczxEHQs4rb60Cxfdi09jTLkRJAecG6MEZoumj8BxQZCAkaW+YvuWguCAySgqkkiNyD1AL4MyP3BFzgaoF2ZXtaGotKTc8c/ChQJkPtnUkHdes5iALGuXQjNzKRE6CJjxAGItrK/tX2h6cQRePYbs40w9kwlyrSKjnMd0tsAss5uWWZc2J8a
Received: from mydomain.com ([***.***.***.***]) by BAY004-MC3F39.hotmail.com over TLS secured channel with Microsoft SMTPSVC(7.5.7601.22712);
Wed, 9 Jul 2014 08:18:05 -0700
Received: from mydomain.com (localhost.localdomain [127.0.0.1])
by mydomain.com (8.14.4/8.14.4/Debian-4) with ESMTP id s69FI3wS030630
for <*********#hotmail.fr>; Wed, 9 Jul 2014 17:18:03 +0200
DKIM-Signature: v=1; a=rsa-sha256; c=simple/simple; d=mydomain.com;
i=#mydomain.com; q=dns/txt; s=selector; t=1404919083; h=MIME-Version
: Content-Type : Content-Transfer-Encoding : Subject : From : To : Date
: Message-ID; bh=k7X+9bPwn6CQYmdYxiU1/FA763QwNClj01j8KmwLN2k=; b=Xg53TzAVYu7/7hnSJpH0NPsXhR2xasyW/Oo37XNSdWGOmZFP95way23mFMgT370IGv/rlTf+LJgYuH1grPRoVgR9Oif89uwLf9FIWx0CTwNlG9ONvKgTX3I91J8lAn/5KaMHW3sF/6C6CYhu9+nP8bh1JcuiuHq3zlYZLv2zQQQ=
MIME-Version: 1.0
Content-Type: text/plain; charset="utf-8"
Content-Transfer-Encoding: 8bit
Subject: Activation de votre compte Mydomain
From: Mydomain <no-reply#mydomain.com>
To: *********#hotmail.fr
Date: Wed, 09 Jul 2014 15:18:03 -0000
Message-ID: <20140709151803.30554.31146#mydomain.com>
Return-Path: no-reply#mydomain.com
X-OriginalArrivalTime: 09 Jul 2014 15:18:05.0604 (UTC) FILETIME=[FB999E40:01CF9B88]
Now I really don't understand what causes the email to be flagged as spam. Also checked blacklists, the domain isn't blacklisted.
I also did a test here, the results are the same : DKIM detected and check PASS, SPF PASS, SpamAssassin Score: -2.011 "Message is NOT marked as spam", only empty box is "DomainKeys Information : Message does not contain a DomainKeys Signature" (I don't find anything explaining the difference with DKIM).
NB : After goncalopp's comment, I wondered if this question shouldn't be on Serverfault instead of here. Should I remove it and ask there?
So after changing few settings I managed to have this header (masked IP address and domain for confidentiality). It sems to be clean header and passes all authentication tests :
Delivered-To: **********#gmail.com
Received: by 10.140.103.77 with SMTP id x71csp25213qge;
Thu, 17 Jul 2014 07:12:51 -0700 (PDT)
X-Received: by 10.180.109.168 with SMTP id ht8mr22242453wib.68.1405606370624;
Thu, 17 Jul 2014 07:12:50 -0700 (PDT)
Return-Path: <no-reply#**********.com>
Received: from mail.**********.com (**********com. [**********])
by mx.google.com with ESMTP id r8si9159599wia.83.2014.07.17.07.12.48
for <**********#gmail.com>;
Thu, 17 Jul 2014 07:12:50 -0700 (PDT)
Received-SPF: pass (google.com: domain of no-reply#**********.com designates ********** as permitted sender) client-ip=**********;
Authentication-Results: mx.google.com;
spf=pass (google.com: domain of no-reply#**********.com designates ********** as permitted sender) smtp.mail=no-reply#**********.com;
dkim=pass header.i=#**********.com
DKIM-Signature: v=1; a=rsa-sha256; c=simple/simple; d=**********.com;
i=#**********.com; q=dns/txt; s=selector; t=1405606368; h=MIME-Version
: Content-Type : Content-Transfer-Encoding : Subject : From : To : Date
: Message-ID; bh=PblNSkQvil33DWRvqe8DinhP7RB+k1OiDCBjgpR7DuE=; b=T4ti1yJsxUE2Uav6UYr+WznqZFrDVvAIoUN8G6voMWr4hUGVdC7u+QkR+d87SY4cN0nklbTWBXJ7gSOhR6r1d0NQZbg3jmRZzYxofPwayMRicYfUw1brWnrSnCUDQ98aUPv4qi9okb2/8vuu5yCKk5irarGrNQk+smnhVEFbqbA=
MIME-Version: 1.0
Content-Type: text/plain; charset="utf-8"
Content-Transfer-Encoding: 8bit
Subject: Activation de votre compte **********
From: ********** <no-reply#**********.com>
To: **********#gmail.com
Date: Thu, 17 Jul 2014 14:12:48 -0000
Message-ID: <20140717141248.2687.75060#**********.com>
It is still going straight to the spam folder. According to what I read here and there, it seems that my domain has to gain "trust" before being considered as "non-spam" (i.e. users have to flag it as "non-spam" and my domain should then be recognized better).
If anyone has any more suggestions, I take with pleasure :)
Hotmail/Outlook has the snds (Smart Network Data Service) you can register your ip and check the reputation, mail volume, bounces, traps. Maybe you have a bad reputation.
https://postmaster.live.com/snds/

Hide my IP address from gmail headers when sending mails via python SMTP library?

I am currently using python SMTP library to send e-mails to certain clients.
I am using the smtp.gmail.com:587 server.
I noticed that in the original headers of any received e-mails sent by this code, the IP address of my own server which sent the e-mail appears.
How can I hide this information ?
Thanks in advance.
server = smtplib.SMTP('smtp.gmail.com', 587)
#server.set_debuglevel(1)
server.ehlo()
server.starttls()
server.login("my gmail account", "gmail account passwd")
server.sendmail(source, [destination], message)
server.quit()
Headers received by such an email.
Delivered-To: XXXXXXXXXXX#XXXXXXXXX.com
Received: by 10.52.117.49 with SMTP id kb17csp32285vdb;
Thu, 5 Dec 2013 09:23:19 -0800 (PST)
X-Received: by 10.66.235.106 with SMTP id ul10mr89187198pac.19.1386264198756;
Thu, 05 Dec 2013 09:23:18 -0800 (PST)
Return-Path: <noreply#XXXXXXX.com>
Received: from mail-pd0-f172.google.com (mail-pd0-f172.google.com [209.85.192.172])
by mx.google.com with ESMTPS id v7si58653928pbi.128.2013.12.05.09.23.18
for <XXXXXXXXXXXX#XXXXXXX.com>
(version=TLSv1 cipher=ECDHE-RSA-RC4-SHA bits=128/128);
Thu, 05 Dec 2013 09:23:18 -0800 (PST)
Received-SPF: neutral (google.com: 209.85.192.172 is
neither permitted nor denied by
best guess record for domain of
noreply#XXXXXXXXX.com) client-ip=209.85.192.172;
Authentication-Results: mx.google.com;
spf=neutral (google.com: 209.85.192.172 is neither
permitted nor denied by best guess
record for domain of noreply#XXXXXXX.com)
smtp.mail=noreply#XXXXXXXXXXXX.com
Received: by mail-pd0-f172.google.com with SMTP id g10so25045148pdj.31
for <XXXXXXXXXXX#XXXXXXXXX.com>; Thu, 05 Dec 2013 09:23:18 -0800 (PST)
X-Google-DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
d=1e100.net; s=20130820;
h=x-gm-message-state:message-id:date:from:to:cc:subject;
bh=q/9aftTaFh6ryLKbZzIDy6Hfz1R4BSYhG2tvHwxCBLU=;
b=C7Ke+Q6gVau5OxK9BZTuFx2ny0lO35WRjgsWoGyjlbQ0hlTRyQbD18ALNnlbdowUzR
JHO8Smvr2EpgTFQ6h9gsLx6V8fmrfpFNWyQWOFgs6h46d9b1TTW7LWQZfVOIfWD6CfgG
7hUTl7/YFcLbuUQpcOMUDJ/LK7AN4Yp6J6n2nzA6m46QOKKSP7t62OCUTlCd9JoLg4D3
zPkF7oFptlyHWwpZCN5FozbqjuLx6rQfaZpKKMd2q4OXsPd0/CwtOOpBaf1BNVF7HOnD
VJR8YrpFI/gpUOfJJz9R5l8DXE8KAkMCW+10OAupdTzwP9gtSk2coHBA+N05Q2ezzDuK
Np3w==
X-Gm-Message-State: ALoCoQn41Nai7QBm96wqd4aNJPrBfx2AlYr+PlZzQ
wAxujazDPTnRQG80l4v/Oy35W/3ZIz6jCIa
X-Received: by 10.68.66.103 with SMTP id e7mr53292154pbt.120.1386264197850;
Thu, 05 Dec 2013 09:23:17 -0800 (PST)
Return-Path: <noreply#XXXXXXXXX.com>
Received: from [127.0.0.1] ([xx.xxx.xxx.xx])
by mx.google.com with ESMTPSA id er3sm145968195pbb.40.2013.12.05.09.23.15
for <XXXXXXXXXXX#XXXXXXXXXx.com>
(version=TLSv1 cipher=RC4-SHA bits=128/128);
Thu, 05 Dec 2013 09:23:16 -0800 (PST)
Message-ID: <52a0b684.a363440a.5bbc.ffff8e2e#mx.google.com>
Date: Thu, 05 Dec 2013 09:23:16 -0800 (PST)
From: noreply#XXXXXXXXXX.com
To: XXXXXXXX#XXXXXXXXX.com
Cc:
Subject: FTP Credentials
Your FTP account credentials are:
User Name = xxxxxxxxxxx
Password = xxxxxx
Those headers are added by the gmail SMTP server. There is no way to hide them.
Have you tried using VPN service like HIDE-MY-IP. They allow you to use different IP from proxies, and not use your own. This way you mask your IP with another one...
I could swear I just checked and gmail was still forwarding x-originating-ip - if not that's great. In the name pf privacy yeah right its in the name of that's our marketing information but anyways - If they do not forward your IP then you are still at risk of having your IP located with many other simple techniques.
Don't kid yourself - Google does track IP addresses there is simply a reason its not in certain cases based on sender and receiver control/ownership.
From here if you decide its not safe enough to simply trust the next email will not contain x originating or that its not tracked in a easy to retrieve way then you can move up the scale:
Public Proxy Configuration and Testing/Validation Cheap, fast, pretty easy but so many way for this to be useless its barely better than going to the library except that a free proxy outta russia may make your email look suspicious or end up in junkmail and many proxy's proxy your IP as well lol
Paid Premium Proxy Services or "Endpoint Protection" such as Anonymizer, Hushmail (server enforced encryption signing and anonymity) , Symantec, or DELL... From a few dollars a month to buckets of cash as joe trucker and the president are both clients to somebody that offers this service at different scales.
Enter open source peer to peer encrypted onion like puzzles over the Tor protocol. Tor is what makes wikileaks work. It's also the entire darknet and is useful in a context of freedom and privacy. The Tor Browser Bundle (TBB) is ok for short term usage
The only serious solution is Tor on a custom live OS that has all the caveats taken care of.
US DoD Anonymous Live Distribution:
http://spi.dod.mil/lipose.htm
And Whonix is a good implementation of Tor that appears to solve a lot of accidental leakages of IP address since it forces all internet through Tor no matter what. Compare this one to others however its probably sufficient:
https://www.whonix.org/

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