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

SMTP (Simple Mail Transfer Protocol) is a widely used protocol for email communication across the WEB. Email clients (like Google Mail or Microsoft Outlook) can use SMTP to send and receive email messages. When a company uses an email client that offers SMTP services, the SMTP server can often 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 log in and navigate to Account –> Litmos Features –> SMTP Server.

Note: If this feature is disabled on the account, please get in touch with 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 related 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. This field also supports using a sender name. To add that, please use the following format Name <email@domain.com> (Example: Litmos Support <support@litmos.com>)
• The “server name” is your SMTP site server name. You can find it while logged into your SMTP site.
• The “Office 365 SMTP server” should be selected by all clients using an Office 365 SMTP server. This ensures that Office 365 SMTP server appropriately delivers all emails to each person. Office 365 enforces throttling and ensures the SMTP relay adheres to throttling limits. You can find these limits for Office 365 at Changes in message store and throttling for concurrent connections.
  • Only select Office 365 if you are using it. If you select it, your emails will be throttled to the Office 365 timing, which could delay the emails.
  • Only check this box if you are using Office 365. If this is not selected and you’re using O365, you can reach the limit, and emails will be missed or not sent out.
• The “port number” is a port number on your SMTP site intended to be used for email transmissions.
• The “username” and “password” are the SMTP site credentials that 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 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 relay messages to email addresses belonging to your 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 or disable the SMTP feature, the email messages will continue to be sent to your end users from the system@litmos.com address.

SMTP Troubleshooting

To properly test the Custom SMTP setup, we need to ensure that the correct server information, including server name, port number, email address, username, and password, is entered in the Custom SMTP settings dialog.

Note: Standard SMTP ports are typically 25 or 587

FAQs

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 your SMTP server’s correct server name or IP address?
   • Here is an excellent 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 servers restrict emails to only be sent from approved email addresses.
5. Are your 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., a number of emails per day or a maximum per minute?
   • Some SMTP servers and services limit the number of messages 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 to sent messages.
8. Do you have logging enabled for your SMTP server?
   • Are there 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 IPs for your region? 
    • See the ‘Allowlisting Domains and IP Addresses to Prevent or Resolve Blocked Content or Blocked Emails’ Knowledge Base Article.

Configuring O365 SMTP Relay for Litmos

While we can send email via an SMTP connection to a regular Office365 mailbox, Microsoft limits the delivery speed and maximum messages per day. An alternative is configuring Office365 SMTP Relay, ensuring 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.

For details, please view “Configuring O365 SMTP Relay for Litmos” in the Integrations guide.