Can someone give me some insight as to why both this: mailServer = smtplib.SMTP("smtp.gmail.com", 587) and this: mailServer = smtplib.SMTP('smtp.gmail.com:587') Are saying this: Traceback (most recent call last): File "<pyshell#23>", line 1, in <module> mailServer = smtplib.SMTP("smtp.gmail.com", 587) File "C:\Users\user\Documents\Shuttlecock_new\python\lib\smtplib.py", line 242, in __init__ (code, msg) = self.connect(host, port) File "C:\Users\user\Documents\Shuttlecock_new\python\lib\smtplib.py", line 302, in connect self.sock = self._get_socket(host, port, self.timeout) File "C:\Users\user\Documents\Shuttlecock_new\python\lib\smtplib.py", line 277, in _get_socket return socket.create_connection((port, host), timeout) File "C:\Users\user\Documents\Shuttlecock_new\python\lib\socket.py", line 571, in create_connection raise err error: [Errno 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'm in China. I have a VPN. I tried it with and without the VPN. I have, many times before, used this code to send e-mails from my g-mail account. Suddenly today, I got this error. Gmail, if accessed through my chrome browser, works fine. Albeit, it's taking an unusually long time to send simple e-mails...hmmm Continue reading...