Failed to set up outbound SSL environment.

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Failed to set up outbound SSL environment.

Post by scngan » Fri Sep 06, 2019 7:36 pm

any idea how can we get more details for the error "Failed to set up outbound SSL environment." ? We seen a lot of this fail message (on our SMTP Debug log) to the server like outlook, gmail and yahoo. checked on the website, no error mention. any idea ?

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Re: Failed to set up outbound SSL environment.

Post by MailEnable-Ian » Fri Sep 13, 2019 12:22 am


Might be that the remote mail server is only accepting TLSv1.2 and you are sending over TLSv1. To confirm you would need to inspect the headers of a message that is sent over TLS.


Below is an example of message sent via TLS1_2

Received: from x.x.x.x ([x.x.x.x]) by with
MailEnable ESMTPS (version=TLS1_2 cipher=TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P256);

To ensure your sending via TLSv1.2 please see the following article:

In the above article locate the section for "TLS 1.2 subkey table". You need to add the "client" key.

Ian Margarone
MailEnable Support

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