Email from on-premises Exchange to gmail

Copper Contributor

Hello Everyone, could you please help me with this issue. 

when I send an email from my  to Gmail. I got the next message: security: did not encrypt this message


I would like to know what is causing this and how can I do to solve it . 


1 Reply
Likely your message could not be delivered (to GMail) using TLS; this can have various reasons. Make sure there is no inspection device for example between your environment and GMail that might filter out STARTTLS keywords from the transport protocol, which would result in sending messages to GMail without TLS, and GMail consequently showing this message.