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I tried to send mails from terminal with a zip file attachment. The mails get rejected by the gmail or google apps mail. I get an error like:

<user@mail.com>: host ASPMX.L.GOOGLE.com[74.125.23.27] said: 552-5.7.0 This
    message was blocked because its content presents a potential 552-5.7.0
    security issue. Please visit 552-5.7.0
    https://support.google.com/mail/answer/6590 to review our message 552 5.7.0
    content and attachment content guidelines. 69si4122998ioc.181 - gsmtp (in
    reply to end of DATA command)
  • The link in your message explains it perfectly does it not? – Rinzwind Feb 18 '16 at 7:47
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Probably your zip file contains prohibited contents set out in Gmail attachment policy.

In short, if the zip file contains executable files, or if the zip file is password protected which contains another zip file, it rejects your email.

Message size (including attachments) of over 25MB are also rejected.

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