DB Mail could not sent mail to the recipients because of the mail server failure in sql server 2012

Question

I have tried to send database mail but the following issue occurs.

The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 3 (2018-11-13T13:05:31).

Exception Message: Could not connect to mail server. (A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond).)

I have done the few configuration as per suggestion in google search but still the same issue occurs.

Below are the steps which I have performed so far.

1. I have enabled is_broker_enabled
2. Enabled inbound and outbound rules for both 465 and 587 ports

3. Ran the following stored procedure

   sp_configure 'show advanced options', 1;
   GO
   RECONFIGURE;
   GO
   sp_configure 'Database Mail XPs', 1;
   GO
   RECONFIGURE
   GO

Answer 1

You can try with Basic authentication, IN User Name: Your mail ID. Password: Your Gmail Password.

Answer 2

None of the suggestions worked for me, other than making sure you do NOT have SSL ticked and Anonymous Authentication ticked only.