Not sure why my email script is not sending an email - python-2.7

Question

It was working but after updating my Raspberry Pi, my python script to send an email is not sending and I'm not sure why. It seems to just hang without throwing any error messages and I have to Ctrl+C to stop it every time, otherwise it'll just sit there indefinitely.
Here is my code...
import smtplib, datetime
from email.mime.text import MIMEText
from email.mime.multipart import MIMEMultipart
from email.mime.base import MIMEBase
from email import encoders
email_send = [sender email]
email_receive = [my email]
password = [password]
subject = 'Test Subject'
#sYMD = datetime.date.today().strftime('%y%m%d')
#lpath = 'C:/Path/to/files/'
files = ['log1.txt', 'log2.txt']
msg = MIMEMultipart()
msg['From'] = email_send
msg['To'] = email_receive
msg['Subject'] = subject
body = """\
Test Message."""
msg.attach(MIMEText(body, 'plain'))
#filename = x.strftime("%y%m%d")+'_log.txt'
for file in files:
part = MIMEBase('application', "octet-stream")
part.set_payload(open(file, "rb").read())
encoders.encode_base64(part)
part.add_header('Content-Disposition',
'attachment; filename="%s"' % file)
msg.attach(part)
text = msg.as_string()
server = smtplib.SMTP('smtp.office365.com', 587)
server.starttls()
server.login(email_send, password)
server.sendmail(email_send, email_receive, text)
server.quit()
Here is what its doing when I run the script...
pi#raspberrypi: python send_email.py
^CTraceback (most recent call last):
File "send_email.py", line 36, in <module>
server = smtplib.SMTP('smtp.office365.com', 587)
File "/usr/lib/python2.7/smtplib.py", line 265, in __init__
(code, msg) = self.connect(host, port)
File "/usr/lib/python2.7/smtplib.py", line 317, in connect
(code, msg) = self.getreply()
File "/usr/lib/python2.7/smtplib.py", line 361, in getreply
line = self.file.readline(_MAXLINE + 1)
File "/usr/lib/python2.7/socket.py", line 480, in readline
data = self._sock.recv(self._rbufsize)
KeyboardInterrupt
Thanks for any help you can give.

Answer 1

Hmm sounds like the connection is timing out. Is it possible the client is unable to connect to the specified server and port? Try connecting directly with nc or telnet to confirm.
You can also pass a timeout value in seconds to the SMTP call:
server = smtplib.SMTP('smtp.office365.com', 587, timeout=5)