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I was trying to send email in a django web app hosted on pythonanywhere. I was trying to use mandrill to send email using smtp , my settings were something like this(I made sure taht there were no typo's in these settings) EMAIL_HOST = 'smtp.madrillapp.com' EMAIL_HOST_PASSWORD = 'valid api key' EMAIL_HOST_USER = 'right username' EMAIL_PORT = 587 # 465 or 587 EMAIL_USE_TLS = True

However these settings werent working(They worked only for the first mail that went out) so I switched to gmail's smtp settings .

But the mail delivery there is unreliable even when the number of mails are under the limit and the security settings in gmail are minimum, I'd like to switch to a more reliable service for sending out mails via SMTP.

Moreover I'm not getting a connection refused error so maybe gmail's smtp servers arent rejecting the mail assuming it's spam. I didnt find anything valuable in the logs either.

It's been pretty hard to set up SMTP with django and mandrill/gmail. Is there some firewall issue or am I doing something wrong? If possible could you help me setup the SMTP settings for madrill or any other such service ?

Are you not getting any emails through for gmail? If so, I think gmail sends you an email to verify that you are trying to connect via their API, and if you missed it and don't click confirm, then nothing will work.