My advice would be to send a test message to a yahoo account you own. Then reply to yourself. Read the headers and the maillog. Something useful should indicating the problem should pop up.

Yo‎u may have to change a log level in one of the postfix cf files. 

From: vod vos
Sent: Friday, November 18, 2016 7:05 PM
To: postfix-users
Subject: How to encrypt the mail content?

Hi,

I have configured the TLS,

when I receive the mail such as yahoo mail,

the mail content is transferred encoding like base64.

When I send mail to yahoo account or others,

the content is clear text,

how to encrypt the content in an acceptable encoding to other mail servers?

Thanks.




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