Why are my emails going to the promotions tab in Gmail? - Knowledge Base

Summary

The relationship between smtp.mailfrom (MAIL FROM/Return-Path) and the 'From' header, and the ability to direct bounces to the sender, is a complex one, as shown by the variety of sources. RFC 5321 initially defines the smtp.mailfrom and Return-Path as identical, in practice, ESPs often manage bounces themselves using a distinct Return-Path. This distinction means bounces are often not returned directly to the sender's 'From' address. There are various strategies discussed, including allowing ESPs to handle bounces for optimization, configuring separate subdomains for bounce processing, or utilizing MX record adjustments. Authentication protocols, such as SPF and DMARC, are critical, because alignment issues between the MAIL FROM and the 'From' header domain can cause deliverability problems. Experts emphasize the importance of monitoring the Return-Path to gain insights into deliverability issues, and also having a system to manage bounce processing and maintain list hygiene.

Key findings

RFC vs. Practice: While RFC 5321 defines smtp.mailfrom and Return-Path as the same, ESP practices often deviate, using a custom Return-Path.
Bounce Redirection: Most ESPs will handle bounces and complaints using automated systems. Typically bounces are not forwarded directly to the sender's 'From' address.
Alternative MX Records: By sending from your systems, and sending the MX elsewhere, it is possible to change the MX to be anything you like and it doesn't have to be your systems.
Security: For larger companies, it is possible to set up custom return paths and monitor those regularly.
Authentication: SPF and DMARC authentication is essential, and alignment issues between the MAIL FROM and the 'From' header domain can cause deliverability problems.
Importance of Monitoring: Monitoring the Return-Path can reveal important deliverability issues and insight into any problems.

Key considerations

Compliance: It is crucial to understand any implications of customising the Return-Path for Deliverability and compliance.
Monitoring: An important part is to ensure you implement a good strategy and system for monitoring any returns and complaints, whether manually or automatically.
ESP: You need to determine whether you will be handling bounces manually or relying on systems provided by your current ESP.
Domain control: Make sure that you have full control of any domain/subdomain being used for the Return-Path in order to accurately track and address any delivery issues.

What email marketers say

12 marketer opinions

The relationship between smtp.mailfrom (MAIL FROM/Return-Path) and the 'From' header, and the ability to direct bounces to the sender, is complex. While RFC 5321 equates smtp.mailfrom and Return-Path, in practice, ESPs often manage bounces themselves. This means the Return-Path, where bounces are sent, can differ from the 'From' header. Some advocate letting ESPs handle bounces for better management, while others suggest configuring separate subdomains for bounce processing and monitoring. Authentication protocols like SPF and DMARC also play a crucial role, as mismatches between MAIL FROM and 'From' header domains can impact deliverability.

Key opinions

RFC 5321: RFC 5321 defines smtp.mailfrom and Return-Path as the same, but this is not always the case in practice.
Bounce Handling: ESPs commonly manage bounces using a custom Return-Path, meaning bounces aren't always sent directly to the sender's 'From' address.
MX Records: An alternative is to send from your systems, and send the MX records elsewhere. This will allow you to change the MX to be anything you like and it doesn't have to be your systems.
Authentication: SPF and DMARC authentication depend on the MAIL FROM domain. Alignment issues between MAIL FROM and 'From' header domains can cause deliverability problems.
Custom Return-Path: Setting a custom Return-Path and monitoring it is useful to pick up insights. This enables you to have a bounces@yourdomain.com inbox and monitor this for issues.

Key considerations

ESP vs. Self-Management: Decide whether to rely on your ESP's bounce management or implement your own, considering the technical expertise required.
Authentication Protocols: Ensure SPF and DMARC records are properly configured to align with your MAIL FROM domain and prevent deliverability issues.
Bounce Monitoring: Implement a system for monitoring bounces, whether through your ESP or by setting up a dedicated Return-Path and analyzing bounce messages.
Security implications: If letting the customer handle the bounce processing be sure to have adequate security measures in place to protect the data and prevent any misuse. Assess your customers capabilities and competence, and whether you can trust them to process the bounces themselves.

Marketer view

Email marketer from Litmus explains the need for careful bounce management using the return-path. They indicate that large senders should set up a subdomain to receive bounces and feedback loop notifications and monitor these. This means the Return-Path is usually different from the From header.

6 Oct 2024 - Litmus

Marketer view

Email marketer from SparkPost clarifies that the Return-Path, also known as the envelope sender or MAIL FROM, is where bounces and other delivery status notifications (DSNs) are sent. It's technically possible to set up the Return-Path differently, but this requires careful configuration and understanding of email authentication protocols.

6 Sep 2022 - SparkPost

What the experts say

2 expert opinions

Both experts emphasize the importance of the Return-Path (MAIL FROM) for bounce management and maintaining good email deliverability. Monitoring the Return-Path allows for insights into delivery problems and feedback loops. A robust bounce management system is crucial for list hygiene and should involve a dedicated MAIL FROM address for receiving bounces.

Key opinions

Return-Path Monitoring: Monitoring the Return-Path is vital for gaining insights into email deliverability issues.
Bounce Management: A good bounce management system is essential for maintaining list hygiene.
Dedicated MAIL FROM: Using a separate MAIL FROM address for bounces is a common practice.

Key considerations

Implement Monitoring: Implement a system for regularly monitoring the Return-Path to identify and address deliverability problems.
Establish Bounce Management: Set up a robust bounce management system to process bounces effectively and maintain a clean email list.
Domain Control: Ensure you control the domain/subdomain used for the Return-Path to effectively monitor and act on any delivery problems.

Expert view

Expert from Word to the Wise explains that it's best practice to monitor your Return-Path for bounces and FBLs. If you're not doing it now, you could be missing a lot of insight into your program. Return-Path (MAIL FROM) should be a domain/subdomain you control so that you can monitor and act on any delivery problems.

3 Feb 2024 - Word to the Wise

Expert view

Expert from Spam Resource points out that a good bounce management system is necessary to handle bounces correctly and ensure proper list hygiene. This usually involves having a separate MAIL FROM address to receive bounces.

9 Oct 2024 - Spam Resource

What the documentation says

5 technical articles

The documentation outlines varying aspects of the Return-Path and MAIL FROM in email delivery. While RFC 5321 links the Return-Path to the MAIL FROM command, Microsoft clarifies its role in bounce messages, separate from the From: header. Oracle mentions the possibility of customizing the Return-Path, especially for large senders. DMARC.org highlights the importance of MAIL FROM alignment for authentication, and Amazon SES details its automatic bounce handling with notifications, without direct bounce-back to the original sender.

Key findings

RFC Definition: RFC 5321 establishes a direct link between the Return-Path and the MAIL FROM SMTP command.
Bounce Destination: The MAIL FROM address is used for bounce messages, separate from the From: header.
Customization: Customizing the Return-Path is possible, particularly beneficial for large senders managing their own bounce processing.
DMARC Impact: DMARC uses the MAIL FROM for bounce reporting, and misalignment can lead to authentication failures.
Automated Handling: Amazon SES provides automated bounce and complaint handling, sending notifications without directly bouncing emails back.

Key considerations

Compliance: Understand the implications of customizing the Return-Path on deliverability and compliance.
Alignment: Ensure the MAIL FROM domain aligns with the 'From:' header domain to avoid DMARC authentication issues.
Bounce Strategy: Determine whether to handle bounces manually or rely on automated systems provided by ESPs like Amazon SES.
Implementation: If customising the return path, understand the implications on the sender policy framework SPF.

Technical article

Documentation from RFC Editor specifies that the receiving MTA must put in the Return-Path: header the information it received from the MAIL FROM: SMTP command. This means the Return-Path is intrinsically linked to the MAIL FROM.

17 Jun 2024 - RFC Editor

Technical article

Documentation from Oracle Help Center explains that it's possible to customize the Return-Path for bounce processing. This is beneficial for large senders who want to manage bounces on their own systems, however they recommend that users understand how this change may impact their deliverability and compliance.

1 Jun 2024 - Oracle Help Center