• What is SMTP and why should I integrate it with Litmos?
• How to setup custom SMTP in Litmos
• SMTP Troubleshooting
• Configuring O365 SMTP Relay for Litmos

What is SMTP and why should I integrate it with Litmos?

SMTP stands for Simple Mail Transfer Protocol. SMTP is a widely used protocol for email communication across the web today. Most of the everyday email clients (like Google Mail or Microsoft Outlook) can employ SMTP to send and receive email messages. When a company uses an email client that offers SMTP services, often times, the SMTP server can be customized to send/receive email messages from a custom email address specified by the SMTP site owner.

Now that Litmos can be connected to an SMTP site, each email message sent from system@litmos.com can be relayed through your company's SMTP site, so that the email message is sent from your SMTP server using the customized email address (i.e. thelearningteam@company.com).

How to setup custom SMTP in Litmos:

 To begin with the custom SMTP setup in Litmos, an Account Owner will login and navigate to Account --> Litmos Features --> SMTP Server. 

(If this feature is not enabled on the account, please contact the Litmos Support team or your Litmos Account Manager.)

Once the SMTP configuration settings are accessible, open the feature configuration and enter the appropriate settings as they relate to your SMTP server. 

• The "from email" is the email address that will be applied to the email message once it is relayed from your SMTP site to the end-user.
• The "server name" is your SMTP site server name. This will be found while logged into your SMTP site.
• The "Office 365 SMTP server" should be selected by all clients using an Office 365 SMTP server. This is to ensure that all emails are delivered properly for Office 365 SMTP server to each person. Office 365 enforces throttling and this setting ensures the SMTP relay adheres to those throttling limits.
• The "port number" will be a port number on your SMTP site that is intended to be used for email transmissions.
• The "username" and "password" are the SMTP site credentials that will authorize Litmos to send email messages to your SMTP site.
• The "test email address" is an email address you can use to test the Litmos system's ability to relay email messages to your SMTP site or an email address belonging to your email client. You can change this address over and over again to to repeat tests across various SMTP sites or email addresses. Be sure to test this first, as it may help uncover network related configurations that could block the system's ability to properly relay messages to email addresses belonging to your email client.

Once this feature is properly tested and configured for your Litmos account, it's important to also be sure that your Litmos account also has the proper "reply-to address" entered on the /settings/email page. This is the address end-users will correspond with, and Litmos 

Should your company ever need to discontinue the use of the SMTP site, simply disable the SMTP feature and the email messages will continue to be sent to your end users from the system@litmos.com address.

SMTP Troubleshooting

1. Have you tried testing the custom SMTP feature? Send a test email using the Custom SMTP setup dialog, if there is an error, a corresponding error message will be shown
2. Are you using the correct server name or ip address of your SMTP server? Here is a good tool to test to make sure your server is receiving inbound requests: https://pingability.com/smtptest.jsp
3. Do you have the correct port setup? Trying using one of the ports above
4. Do you have any sending email addresses allowlisted? Many SMTP server restrict emails to only be sent from approved email addresses.
5. Are you username and password correct? Sometimes they correspond to the sending email address.
6. Are there sending limits or throttling on your SMTP server? i.e. number of emails per day or maximum per minute? Some SMTP servers and services limit the number of messages that can be sent per day, hour, or minute.
7. Do you have a secondary firewall or spam filter? Sometimes these services can block or reject messages sent through your SMTP server. Litmos does not add additional DKIM records on to sent messages.
8. Do you have logging enabled for your SMTP server. Can you check to see if there are any incoming requests that are being blocked?
9. Could the reputation of your SMTP server or specific sending email/domain be bad? If your reputation is low mail may not be delivered to some recipients. You can check your score at this website https://www.senderscore.org/
10. Have you allowlisted all Litmos IP’s for your region? Allowlisting Domains and IP Addresses to Prevent or Resolve Blocked Content or Blocked Emails

Configuring O365 SMTP Relay for Litmos

While we can send email via a SMTP connection to a regular Office365 mailbox,
Microsoft places limits on the delivery speed and maximum messages per day[1]. An alternative
is to configure Office365 SMTP Relay which will ensure your mail client does not limit or block
emails sent from Litmos. The majority of this work will need to be conducted by whoever has
full admin access to your organization’s account, such as your Mail and/or DNS Administrator,
as they will need to sign into https://admin.microsoft.com/AdminPortal. 

Please view article Configuring O365 SMTP Relay for Litmos for details.