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Hi, it's funny that you chose this example.

I wonder though how I should send some (around 200 mails) by SMTP without getting flagged as spam.

I had one approach iterating over a list but it takes quite long with lots of logging in and out. Currently I implemented some logic with logging in and then sending as many mails as possible in an try...except block and if the connection times out it reconnects. What is the best way to do this without resorting to dedicated, paid services?

Best regards!

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There is no simple answer to that. The reason there those paid services have such a success is that they provide more than a technical answer to the problem: they have won trust over the network, which is a huge amount of work that is far beyond code.

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