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I’m using python’s sendmail in the following way:
msg = <SOME MESSAGE>
s = smtplib.SMTP('localhost')
s.sendmail(me, you, msg.as_string())
s.quit()
This usually works fine (I.e I get the email) but it fails (I.e no exception is shown but the email just doesn’t arrive) when the message is pretty big (around 200 lines). Any ideas what can cause this?
Who are you sending to? You should consider some email servers (such as Yahoo and Hotmail) quarantine incoming email for a period of time if the email is categorized as potential spam. Spamminess is going to be a function of the content, image to text ratio, nature of attachments, nature of html links, sending rate, number of duplicates, sender, and numerous other factors.