Develop Reference

Sending email via Outlook using Python, contact group doesn't resolve

The recipient address and the distro lists do not immediately resolve. Outlook is smart enough to recognize the email addresses, but it doesn't recognize my distro list. At least not immediately.
I'm using Office 365 if that matters.
from win32com.client import Dispatch
outlook = Dispatch('Outlook.Application')
Mail_Item = outlook.CreateItem(0)
# This sends no problem
# Mail_Item.To = 'first.last#company.com'
# This does not send
Mail_Item.To = 'Contact_Group_Test'
Mail_Item.Subject = "Subject_text"
Mail_Item.Body = "Body_text"
Mail_Item.Recipients.ResolveAll()
Mail_Item.Send()
While troubleshooting I used Mail_Item.Display() to see the message. After a few seconds it resolves all my addresses, including the contact group. HOWEVER, the contact group itself still doesn't work despite this.

If you couldn't solve, you can try smtplib.
import smtplib
sender = 'from#fromdomain.com'
receivers = ['to#todomain.com']
message = """From: From Person <from#fromdomain.com>
To: To Person <to#todomain.com>
Subject: SMTP e-mail test
This is a test e-mail message.
"""
try:
smtpObj = smtplib.SMTP('localhost')
smtpObj.sendmail(sender, receivers, message)
print "Successfully sent email"
except SMTPException:
print "Error: unable to send email"
If you will send mail from outlook account, you have to write smtp-mail.outlook.com instead of localhost

mtbenj's answer may work for others. I'm just choosing to go the win32com route because of my organization.
For whatever reason using 'Test', and I'm assuming, any one-word contact list takes ~5 seconds to resolve. I counted after the .Display() popup came up. Naming it 'Test_' didn't do it for me either.
I decided to try one named 'Test_Test'. After calling .Recipients.ResolveAll(), it works perfect.
So use an underscore and multiple words.

DKIM fails when sending mails with smtplib

I'm trying to send emails with smtplib and they seem to be delivering fine. The only problem is that DKIM fails and the mails usually go straight to the spam folder.
DKIM is enabled on my shared hosting (host is a2hosting, if that helps) and the process works fine when sending individual emails with Thunderbird, and DKIM passes, suggesting that the problem lies on my end.
I even tried using dkimpy to explicitly sign the emails using the private key but I still get dkim=fail under ARC-Authentication-Results.
Some posts and answers I referred to suggested "logging in" as the solution but I am already logging in using SMTP.login() and as I mentioned earlier, the emails are being sent.
An answer I referred to mentioned that it is the server's job to sign the email and it's worth mentioning that the raw email output includes the DKIM signature, even without explicitly signing it with dkimpy, indicating that the server is signing as expected.
But the problem remains that DKIM fails affecting the email deliverability, and the raw output does not provide any details as to why DKIM failed for the domain.
I use the following code snippet to send an email
msg = MIMEMultipart()
msg['From'] = 'myemail#mydomain.tld'
msg['To'] = 'someemail#gmail.com'
msg['Subject'] = "Subject"
msg.attach(MIMEText("SomeText", "plain"))
s = smtplib.SMTP_SSL("mydomain.tld:465")
s.login("myemail#mydomain.tld", "mypassword")
s.sendmail("myemail#mydomain.tld", 'someemail#gmail.com',msg.as_string())
I tried signing the message as follows
headers = ["To", "From", "Subject"]
with open("cert.pem") as fh:
dkim_private = fh.read()
sig = dkim.sign(
message=msg.as_string().encode("ascii"),
selector=str(dkim_selector).encode("ascii"),
domain="robogyan.tech".encode("ascii"),
privkey=dkim_private.encode("ascii"),
include_headers=headers,)
msg["DKIM-Signature"] = sig.decode("ascii").lstrip("DKIM-Signature: ")
The raw output did reflect the signature with the above code but DKIM still failed.
There seems to be no problem with the authentication whatsoever since the server replies with "Authentication succeeded"
Edit:
DKIM-Signature: v=1; a=rsa-sha256; q=dns/txt; c=relaxed/relaxed;
d=mydomain.tld; s=default; h=Subject:To:From:MIME-Version:Content-Type:
Sender:Reply-To:Date:Message-ID:Cc:Content-Transfer-Encoding:Content-ID:
Content-Description:Resent-Date:Resent-From:Resent-Sender:Resent-To:Resent-Cc
:Resent-Message-ID:In-Reply-To:References:List-Id:List-Help:List-Unsubscribe:
List-Subscribe:List-Post:List-Owner:List-Archive;
bh=giCDGo/0duFr1Ex65l7Ixc3N45EAULK+gw5cHV8pO0k=; b=DR08Q+CjgOLqo8WkLJs/XROfTw
Z7+ph+qnzi5p49cT3+UwQolcL1CKIVPk7XRkL8WZ3FFa9hZuc6TumquRSiYd5uR0AC5Z3lopEfnQe
fdbOOTRnks2ZzoOnQusy/gmydUttypu8wTthFhy7vTWXMFcdI29X/HkrokCtiGKCoD2u2kWBtn2sm
3/aP83lBbMpcWsNbvo3HTsL71o8QPd6bVKpqRGyAy89cAwMLwP4dnJ9WcCxxNzowlJNPQja3o5W16
t3rG/KizcRehjaDUXhPPRF/4RdYUSIi/SGNwmIPwvkZNc17k3wQpszKeG6/Ujgax/i7Li7V7dLJBT
Fu/x6xDA==;
Signed-by: myemail#mydomain.tld
Expected-Body-Hash: giCDGo/0duFr1Ex65l7Ixc3N45EAULK+gw5cHV8pO0k=
Here's the DKIM of the failing email if that helps. The expected body hash and the received body hash match too. I am not sure what the problem is then.

After a lot of research and brute force approaches, I finally found the solution to my problem.
I needed to include the Message-ID and the date in the headers as well.
Adding the following lines to the code helped me pass the verification.
msg['Date'] = email.utils.formatdate()
msg['Message-ID'] = email.utils.make_msgid(domain='mydomain.tld')

Important note: you need to add your smtp client's machine IP address to InternalHosts list, because OpenDKIM will check client's permission with these rules.
The you need to add this line to your /etc/opendkim.conf:
InternalHosts file:/etc/opendkim/TrustedHosts # or any location you want
Content of /etc/opendkim/TrustedHosts could look like:
127.0.0.1
::1
localhost
<server_ip>
hostname.example1.com
example1.com
hostname.example2.com
example2.com
...
It's just for example. You need to put here your python smtplib-client machine's address (ip/host).
Then just restart your opendkim:
$ sudo service opendkim restart

Python sending e-mail with SMTP without authentication

I'm making a script that notifies people about some pending tickets in JIRA. These notifications are sent by e-mail, I already got the notification to trigger, but I'm having problems sending the emails.
I can send them using gmail but when I tried to do it with my official account (the one that the company gave me) I am not able to send them. IT guys already provided me the 'localhost' because they use SMTP relays and the port, but they keep telling me that I should start SMTP without authentication, I'm not very sure of how to do this.
The example I found on internet was this:
import smtplib
fromaddr = 'Axel.Sa#mydomain.com'
toaddrs = ['Axel.Sa#mydomain.com']
msg = '''
From: {fromaddr}
To: {toaddr}
Subject: testin'
This is a test
.
'''
msg = msg.format(fromaddr=fromaddr, toaddr=toaddrs[0])
server = smtplib.SMTP('localhost:25')
server.starttls()
server.ehlo("mydomain.com")
server.mail(fromaddr)
server.rcpt(toaddrs[0])
server.data(msg)
server.quit()
But I keep getting this error, If someone can tell me the proper way of sending emails by SMTP without authentication I will be very grateful.

Check this stack:
How to send an email without login to server in Python
change your smtplib.SMTP('localhost:25') to smtplib.SMTP('localhost', 25)

Send email to a mailing list using Python

I'm trying really hard to check why this is happening but not really sure if its on gmail's server side or in a part of the script I'm using.
The problem is that I'm trying to send an email to a mailing list (I have found many posts explaining how to include various emails but none explaining if there is a limitation or workaround to send it to a single email which contains multiple addresses).
In this case I want to send the email to many different people which make part of the BI team of our company (bi#company.com), normally sending an email to this address will result in everyone from the team getting the email, but I can't manage to make i work, and I don't want to include all emails in the list because there are too much and it will have to be manually changed every time.
When I try this with another single person email it works perfectly
import smtplib
sender = 'server#company.com'
receivers = ['bi#company.com']
q = ""
message = """From: Error alert <Server-company>
To: BI <bi#company.com>
Subject: Error e-mail
%s
""" % q
try:
smtpObj = smtplib.SMTP('localhost')
smtpObj.sendmail(sender, receivers, message)
print "Successfully sent email"
except SMTPException:
print "Error: unable to send email"

Alright. I found out why this was not working in my organization. Hopefully this can help someone else out. The outlook groups were setup to only work from an internal email address.
Sending emails programmatically, may use a relay method, which has no authentication. As such the email will never go through. The fix is to have the Network ops people (or exchange group) at your company turn on receiving external emails. The emails will then go through.

make recivers a list of emails you want to send:
example:
recivers = ['a#gmail.com','b#gmail.com,...]
try like this:
import smtplib
from email.mime.text import MIMEText
sender = 'server#company.com'
receivers = ['a#company.com','b]#company.com'....]
server = smtplib.SMTP('smtp#serv.com',port)
server.starttls()
msg = MIMEText('your_message')
msg['Subject'] = "subject line"
msg['From'] = sender
msg['To'] = ", ".join(receivers)
server.login('username','password')
server.sendmail(sender, recipients, msg.as_string())
server.quit()

I finally decided to stick to writing the full list of email addresses inside the list. Apparently if mailing lists are managed locally the re distribution of the emails cant be done.

Email sent via sendmail showing wrong 'from' address when sent via text message

I have a cronjob that runs a python script to periodically send an email with status updates to me. On the weekend I prefer this to work via text, so I send it to myphonenumber#vtext.com. This works fine, except the 'from' address is incorrect when it goes to the phone. It shows correctly when it is sent to a regular email address. For some reason when it goes through a text it shows the 'from' address as "myusername#servername.wndowsdomain.local". This may simply be a verizon text message thing specifically, but if possible I'd like to figure out how to fix it as I hope to add some reply functionality to this tool.
The machine that the script is on is running Ubuntu 12.04.
Here is the simple python function I have that sends the email:
def sendMail(to,text):
msg = MIMEMultipart('alternative')
msg['Subject'] = "Weekend Report"
msg['From'] = 'servername#mydomain.com'
msg['To'] = to
msg.attach(MIMEText(text,'plain'))
p = Popen(["/usr/sbin/sendmail", "-t"], stdin=PIPE)
p.communicate(msg.as_string())
Would I be better off using something like smtplib and a gmail account or something perhaps?

Sendmail: Setting envelope sender
You may try to set "envelope sender" address too (sender address used in SMTP session).
p=Popen(["/usr/sbin/sendmail","-t","-i","-fservername#mydomain.com"],stdin=PIPE)
Comment: I have added missing -i command line option unrelated to setting envelope sender.