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Email Delivery Configuration — Email Relay

This article outlines how to configure Email Delivery when you're using Email Relay setup. Please see this article for instructions how to configure Direct Email Delivery.

Introduction

This a high level overview of how Email Delivery will flow from LiquidFiles when using an Email Relay Server:

Please note that an Email Relay Server in this example can be a local Microsoft Exchange Server, Microsoft Office 365 cloud email server, Google Mail, Amazon SES (Simple Email Service) or pretty much any other email server or service that can accept emails and forward them on your behalf. Feel free to do a web search for SMTP Relay Service to get more options.

Fundamental Concepts

(SMTP) Email is a pass the bucket system. You deliver the email to a Mail Server, that delivers it to the next Mail Server, that delivers it to the next Mail Server... Until it has reached the final mailbox, or one of the Mail Servers decides to either Drop or Reject the email.

Each Mail server on the way are responsible to deliver the email to the next Mail Server. After the email has been accepted by the next mail server the email is no longer the original or current mail servers responsibility.

Further to this concept, once an email has been accepted by the next mail server, there's Nothing that LiquidFiles or the current mail server can do about that email.

Troublshooting Email Delivery then boils down to investigate if the email was Accepted by the next mail server or not. If it was accepted, we have to move to the next mail server and investigate there, and the next mail server, until we eventually find either that the email was successfully delivered, or it was dropped or rejected by the email server we're currently investigating. If an email is dropped or rejected, there will be a log to why the email was dropped or rejected.

If a mail server drops an email it "should" send a non-delivery message back to sender, but for security reasons many do not.

Configuration

Network Level Configuration

In most cases, all the configuration that's required to configure sending emails using an Email Relay Server or Service is in the Email Relay section in Admin → Configuration → Email, looking like this:

The only required options is Email Relay host which can be something like:

  • mail.liquidftest.com — lookup the name mail.liquidftest.com and use the default SMTP port TCP 25 to deliver the email to the Email Relay host.
  • mail.liquidftest.com:587 — lookup the name mail.liquidftest.com and use the specified TCP port 587 to deliver the email to the Email Relay host.
  • 10.2.3.20:587 — use the specified IP address and TCP port 587 to deliver the email to the Email Relay host.

Some Email Relay Servers or Services will require Authentication and if required you can specify a username and password that will be used for

Email Security Level

By default, LiquidFiles will try to deliver the email with TLS encryption. In some cases, you may need to tweak this configuration to match your Email Relay Server setting, please consult the support or documentation of the Email Relay Server or Service if you think you need to adjust this configuration.

Email Sender Configuration

When an email is being delivered, it has a typical header looking like:

From: Friendly Name <someuser@mycompany.com>
To: somerecipient@theircompany.com
Subject: Some Subject

The important bit for this configuration is the From: header. The From: header is made up of a Friendly Name, that could be anything, and the actual email address within brackets.

For security reasons many Email Servers will only allow you to send as the user you've authenticated as. In the Email Relay Username above, you can see the username being support@liquidftest.com which means that the From: header needs to match this and always use: support@liquidftest.com as the email address regardless of whomever in LiquidFiles has sent the message.

This setting can be configured at the top of Admin → Configuration → Email:

If the "Use The Email Sender Address as from address for all emails" is enabled and the Email Sender address is set as: support@liquidftest.com, if a user john.doe@liquidftest.com is logged in and sends a message, the Email Header From address will read:

From: john.doe@liquidftest.com <support@liquidftest.com>
To: somerecipient@theircompany.com
Subject: Some Subject
Reply-To: john.doe@liquidftest.com

This satisfies the requirement that all emails will use the Email Sender Address as the From address when sending emails, while still showing the end recipient who the real sender is, and also allows them the hit "Reply" in their email client and having the emails come back to john.doe@liquidftest.com.

Some people don't like this, and strictly speaking, sending on behalf of someone else could be seen as not correct from a strict email policy perspective, and LiquidFiles will cater for this stand as well. If you disable the "Use The Email Sender Address as from address for all emails" setting, with the same premise that john.doe@liquidftest.com is logged in and sends a message, the email header will now read:

From: john.doe@liquidftest.com
To: somerecipient@theircompany.com
Subject: Some Subject

Please check with your email relay server or service. Some have configuration that will enable them to act as an "unrestricted" email relay server or service, allowing any From address to being used. If you can configure your Email relay server or service in this way, feel free to use this configuration.

Mail Relay Delivery & Troubleshooting

Please see the Troubleshooting Article for documentation how to troubleshoot email delivery issues.