Failed to set up outbound SSL environment.

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scngan
Posts: 445
Joined: Fri Dec 30, 2005 1:27 pm

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 checktls.com website, no error mention. any idea ?

MailEnable-Ian
Site Admin
Posts: 8975
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: Failed to set up outbound SSL environment.

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

Hi,

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.

Example:

Below is an example of message sent via TLS1_2

Received: from x.x.x.x ([x.x.x.x]) by mailenable.com 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:

https://docs.microsoft.com/en-us/previous-versions/windows/it-pro/windows-server-2012-R2-and-2012/dn786418(v=ws.11)#BKMK_SchannelTR_TLS12

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

Ian Margarone
MailEnable Support

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