Failed to set up outbound SSL environment.

[scngan]

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]

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.

[knu]

Hi, we are having the same problem. We have activated TLS1.2 but we still have the "Failed to set up outbound SSL environment." error

Mails to gmail, hotmail are delayed specially the ones with attachments

Debug delivery information for Message ID [EE39B39CE1DB4C408A1E9D9FA0046389.MAI]
03/22/21 08:16:42 ME-I0018: [9232392250734B679BB8C34785616E77.MAI] Outbound message from ([SMTP:*****@****.com]) requeued as [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] to the target domain [gmail.com]
03/22/21 08:16:42 ME-I0026: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] Sending message
03/22/21 08:16:42 ME-IXXXX: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] DNS resolved to the following record: IP Address=64.233.186.27, Family=2, Type=1, Protocol=6
03/22/21 08:16:42 ME-IXXXX: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] Failed to set up outbound SSL environment.
03/22/21 08:18:26 ME-I0148: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] DATE (DATA Termination) command failed with temporary return code.
03/22/21 08:18:26 ME-E0034: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] DATA command returned with a 421 response, meaning that the entire message should be retried.
03/22/21 08:18:26 ME-I0009: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] Remote server has closed connection after 0 milliseconds. Server Response: (-)
03/22/21 08:18:26 ME-E0033: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] DATA Transmission failed.
03/22/21 08:18:26 ME-E0059: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] Message Delivery Failure. Attempt (0): Domain (gmail.com) returned temporary error for email. Message has been requeued.
03/22/21 08:26:41 ME-I0026: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] Sending message
03/22/21 08:26:41 ME-IXXXX: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] DNS resolved to the following record: IP Address=64.233.186.26, Family=2, Type=1, Protocol=6
03/22/21 08:26:42 ME-IXXXX: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] Failed to set up outbound SSL environment.
03/22/21 08:33:15 ME-E0011: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] Failed to send socket data to remote server (error 10054).
03/22/21 08:33:15 ME-E0029: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] DATA Command Failed. Transmit File: Communications Error Transmitting File to gmail.com.
03/22/21 08:33:15 ME-E0033: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] DATA Transmission failed.
03/22/21 08:33:15 ME-E0048: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] - Transmission errors occurred during delivery. Message has been re-queued.
03/22/21 08:56:41 ME-I0026: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] Sending message
03/22/21 08:56:41 ME-IXXXX: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] DNS resolved to the following record: IP Address=64.233.186.26, Family=2, Type=1, Protocol=6
03/22/21 08:56:41 ME-IXXXX: [EE39B39CE1DB4C408A1E9D9FA0046389.MAI] Failed to set up outbound SSL environment.