I am trying to send mail with python using my rouncube webmail but when i run it outputs this error TimeoutError: [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 I checked in my mail and my port is "290" which have provided but when i run the function the mail doesn't send. I know how to send with gmail by turning on less secure app access but don't know how to work around to send with my webmail. I need your suggestion to work around it. from smtplib import SMTP_SSL as SMTP import logging, logging.handlers, sys from email.mime.text import MIMEText def send_message(): text = ''' Hello, Trying to send mail from my webmail in python 3. Sincerely, My name ''' message = MIMEText(text, 'plain') message['Subject'] = "Email Subject" my_email = 'joe@mycompany.com' # Email that you want to send a message message['To'] = my_email # You need to change here, depending on the email that you use. # For example, Gmail and Yahoo have different smtp. You need to know what it is. connection = SMTP('smtp.roundcube.com', 290) connection.set_debuglevel(True) # Attention: You can't put for example: 'your_address@email.com'. # You need to put only the address. In this case, 'your_address'. connection.login('fred.kings', 'fredsw321a') try: # sendemail(<from address>, <to address>, <message>) connection.sendmail(my_email, my_email, message.as_string()) finally: connection.close() send_message() Continue reading...