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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.

Any idea of how to spoof an email sender in python using smtplib?

I was wasting another day of my life messing around with python and I was thinking about how to spoof an email address using smtplib in python. I thought it could be possible to spoof the from address by using the code below but it didn't work. I have seen projects on github that seem to be able to actually spoof the email but if i were to create a program of my own that does this, how exactly would it work? Any ideas? Code:
import smtplib
username = (mygmailusername)
password = (mypassword)
fakefrom = "donaldtrump#gmail.com"
toEmail = (toAddress)
server = smtplib.SMTP("smtp.gmail.com",587)
server.starttls()
server.login(username,password)
server.sendmail(fakefrom,toEmail,"this is the fbi. OPEN UP")
server.close()

Most providers check the account with the sender address, and disallow if the sender address dosn't match with sender. Try if you have a setup box network, to use your provider network smtp server without authentification on smtp 25 port, and most of time the mail can be sent. But with that method, many receiver servers will tag directly this mail as spam/dangerous. You can try that directly in your message tool (outlook,...) it s the same behavior as you code.

Sorry I'm a bit late. The problem, here lies with the second-to-last line:
server.sendmail(fakefrom,toEmail,"this is the fbi. OPEN UP")
You are trying to use the 'fake from' address to actually send the email which isn't what you want to be doing. You just want to 'spoof' it and make the recipient think that the email came from a different address. You do that by defining the sender details in the message body.
The code that you would need to use to make this work would be:
import smtplib
username = (mygmailusername)
password = (mypassword)
fake_from = "donaldtrump#gmail.com"
fake_name = "Donald Trump"
to_email = (toAddress)
to_name = (toName)
subject = "Bonjour"
content = "This is the fbi. OPEN UP"
message = f"From: {fake_name} <{fake_from}>\nTo: {to_name} <{to_email}>\nSubject: {subject}\n\n{content}"
server = smtplib.SMTP("smtp.gmail.com", 587)
server.starttls()
server.login(username, password)
server.sendmail(username, to_email, message.encode())
server.close()

Gmail API Oauth2 Send from different address

I am able to send e-mails using Python and the google libraries (googleapiclient, google_auth_oauthlib.flow, and google.auth.transport.requests). I'm trying to get an alternate "from" or "reply-to" address, and it's not working. My code for creating a message is like so:
# Returns an e-mail message suitable for submission through the gmail api.
def create_message(sender, to, subject, message_text):
message = MIMEMultipart()
message['to'] = to
#message['from'] = sender
message['from'] = 'derp#nowhere.com'
message['subject'] = subject
message.attach(MIMEText(message_text, 'html'))
return {'raw': base64.urlsafe_b64encode(message.as_string().encode()).decode()}
As you can see, I've adjusted the from attribute of the message. When this message is sent, it is from the gmail account owner, not "derp". How do I make the message come from a different address?

Add the e-mail address as whom you want to issue e-mail as a "Send Mail As" account: https://mail.google.com/mail/u/2/#settings/accounts. It is necessary for that other account to verify he has control of that e-mail address.
It appears not to be possible to "spoof" e-mails using gmail oauth without this verification process, though if you use the deprecated "less secure apps", it is still possible.

How do I stop Outlook/Office365 from changing a header?

I am using the Python library smtplib to send Email messages with Office365 as the SMTP server. Everything was fine until a few days ago when my From: header seemed to not be processed. The Python code I am using:
import smtplib
from email.mime.text import MIMEText
def login():
server = smtplib.SMTP(mail.mail_server, mail.mail_port)
server.starttls()
server.login(mail.mail_username, mail.mail_password)
return server
def send(subject, body):
msg = MIMEText(body)
msg["From"] = mail.mail_from
msg["To"] = ", ".join(mail.mail_to)
msg["Subject"] = subject
server = login()
server.sendmail(mail.mail_username, mail.mail_to, msg.as_string())
server.quit()
send("test", "test")
What is strange is that if I log onto Outlook or OWA, I can see my header if I view the sent message details. I sent a test header of From: xxxx <info#...>
However on the recipients inbox message, the header is simply the Office365 User's name and the info address as shown above (From: Name <info#...>). The xxxx custom header is gone.
What can be causing my header to be dropped?

While it may not be an ideal solution, I ended up setting up a new email account with the name I wanted and used that, instead of trying to force the From: header.

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.