Error / delay sending to gmail / hotmail

[knu]

Hi, how are you.
Since some days ago, we are having message delayed in our mailenable outbound queue, specially the ones with attachments to gmail and hotmail

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.



We found this in this forum and made it, but still have the some problem
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 smtp Ourbound configuration we have TLS (Send using TLS if remote server supports it) and the server has a valid SSL certificate

[MailEnable-Ian]

Hi,

Have you tried installing OpenSSL on your MailEnable server and trying to perform an OpenSSL test connecting to the Gmail servers to see this works?