I'm new to EVO. (taken over an old business)
 
Spent couple of days trying to configure print-to-Email function, I found when using Secure SMTP (SSL), EVO just sends out emails once a while and most of the test emails got lost without any error message, I also noticed some .txt files related to the missing emails were created in EVO folder with a random number name, when I replaced the Secure SMTP with a Non-SSL SMTP, all the test emails were sent out successfully and there was a pop-up message showing "Email sent successfully" after click "Send" button and wait for a while.
 
I have snapped some screenshots but don't know how to upload.
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Is there anyone can help me?
 
Thanks,
 
Shawn
 
Stud Welding Systems

I believe if you are using with SSL, then you are expecting the generated email to be encrypted with a set of keys, hence you need to be using an SSL certificate when communicating with the mail relay server for that encryption to occur.  
 
Port 465 was actually deprecated in favor of using TLS to send email securely.  The protocol a mail server uses for secure TLS communications is STARTTLS and allows mail servers to communicate over regular SMTP ports with encryption.  
 
So all your sending server needs is to be able to support using the connection command "STARTTLS" in the SMTP command to send mail to your relay.