What could be the purpose of a spammer sending emails with invalid 'To' addresses and valid 'Return-Path' addresses?

Summary

Spammers exploit emails with invalid 'To' and valid 'Return-Path' addresses for a variety of reasons, including arbitrary behavior and address rotation. A key use is backscatter spam to flood recipients or hide origins. This technique enables testing email verification tools for list cleaning, harvesting addresses from auto-replies, and testing anti-spam filters. It also facilitates bounce address tagging, DDoS attacks, manipulation of sender reputation, and identity masking. Analyzing email variety is crucial to differentiate between planned attacks and software errors. Furthermore, it's related to list bombing, SMTP envelope manipulation, directory harvesting, and protocol violations. Stricter address verification, bounce message monitoring, adherence to email protocols, and enhanced server security are recommended.

Key findings

  • Arbitrary Behaviour: Spammer actions and spam software are unpredictable.
  • Backscatter Spam: Invalid 'To' generates bounces to valid 'Return-Path', flooding recipients or obscuring the source.
  • Address Harvesting: Harvesting valid email addresses from auto-replies and bounce messages.
  • Filter Testing: Testing spam filters to adapt spam techniques.
  • DDoS: Potential use in DDoS attacks.
  • List Bombing: Testing lists to find active addresses.
  • Identity Masking: Hiding identity and complicating traceback efforts.
  • Protocol Violation: Violating email protocols by creating malformed email systems.

Key considerations

  • Monitor Bounce Rates: High bounce rates may indicate spam activities.
  • Analyse Return Path: Investigate the return path for suspicious patterns.
  • Implement Robust Filters: Utilizing solid anti-spam filters to detect and block malicious emails.
  • Address Verification: Validating email addresses before sending.
  • Compliance with email protocols: Ensure compliance with standards

What email marketers say
9Marketer opinions

Spammers utilize emails with invalid 'To' and valid 'Return-Path' addresses for a variety of purposes. These include backscatter spam campaigns to flood recipients or obscure the spam's origin, testing email verification tools to clean and refine target lists, harvesting valid email addresses from auto-replies, testing anti-spam filters, and conducting bounce address tagging to identify active users. They might also attempt distributed denial-of-service (DDoS) attacks or manipulate sender reputation systems. Furthermore, using this method can enable masking their identity and complicating traceback efforts. Another less sinister use is testing an auto-ack email.

Key opinions

  • Backscatter Spam: Invalid 'To' addresses generate bounce messages to the valid 'Return-Path', flooding the recipient or obscuring the original spam source.
  • List Cleaning: Spammers test email verification tools to identify valid addresses, refining their target lists.
  • Address Harvesting: Valid email addresses are harvested from auto-replies and bounce messages.
  • Filter Testing: Spammers test anti-spam filters to identify weaknesses and adapt their techniques.
  • Bounce Tracking: Used for bounce address tagging to track open rates and identify active users.
  • DDoS Attacks: Generate high volumes of bounce messages to overwhelm email servers.
  • Reputation Manipulation: Attempt to trick reputation systems by simulating list cleaning.
  • Identity Masking: Obscure true identity and complicate traceback efforts.
  • Auto Ack Testing: Used to test and receive Auto Acknowledgement of Emails from servers

Key considerations

  • Monitor Bounce Rates: High bounce rates may indicate spam activity or list quality issues.
  • Analyze Return-Path: Investigate the 'Return-Path' address for suspicious patterns.
  • Implement Anti-Spam Measures: Utilize robust anti-spam filters to detect and block malicious emails.
  • Sender Reputation: Regularly check sender reputation to avoid being flagged as a spammer.
  • Address Verification: Consider using email verification services to validate email addresses before sending.
  • DMARC, SPF and DKIM: Consider implementing these email protocols to better authenticate your emails.
Marketer view

Email marketer from Reddit explains that this could be a form of backscatter spam, where the spammer uses an invalid 'To' address to generate bounce messages (NDRs) to a valid 'Return-Path' address. The purpose may be to flood the recipient with unwanted messages or to obscure the original source of the spam.

May 2024 - Reddit
Marketer view

Email marketer from CyberNews explains that spammers use invalid "To" and valid "Return-Path" addresses in order to mask their true identity. By causing errors in the email system, they can redirect attention away from their actual origination point, making tracking and traceback significantly harder.

December 2021 - CyberNews
Marketer view

Marketer from Email Geeks raises a possibility of an auto-ack spam scenario where the spammer sends mail to their own freemail account with auto-ack enabled (containing the spam content) and sets the victim as the sender.

November 2021 - Email Geeks
Marketer view

Email marketer from Random Forum explains that using invalid 'To' addresses and valid 'Return-Path' addresses could be part of a distributed denial-of-service (DDoS) attack against email servers. By generating a high volume of bounce messages, spammers can overwhelm the server and disrupt its normal operation.

November 2022 - Random Forum
Marketer view

Email marketer from Email Hippo explains that spammers might send emails with invalid 'To' addresses and valid 'Return-Path' addresses to harvest valid email addresses from auto-replies and bounce messages. By monitoring the responses and bounce reports, spammers can identify active and engaged email addresses for future spam campaigns.

December 2023 - Email Hippo
Marketer view

Email marketer from Email Marketing Forum explains that the spammer may be attempting to manipulate sender reputation systems. By sending to invalid addresses and receiving bounce messages, they might try to trick the reputation system into thinking they are a legitimate sender, as they are seemingly 'cleaning' their list.

July 2023 - Email Marketing Forum
Marketer view

Email marketer from StackExchange says that a spammer might use invalid 'To' addresses to test the effectiveness of anti-spam filters and identify weaknesses. By observing how the filters react to these malformed emails, they can adapt their techniques to bypass them.

November 2021 - StackExchange
Marketer view

Email marketer from MailerCheck shares that using invalid 'To' addresses could be a method to test email verification tools and identify which addresses are valid or invalid. Spammers might use this technique to clean their lists, identify active email addresses, and improve their targeting.

July 2024 - MailerCheck
Marketer view

Email marketer from Security StackExchange suggests this could be a basic method of bounce address tagging. Where spammers uses it to track open rates based on auto generated 'out of office' replies, which they can use to identify the most active users in that domain, so they can focus their efforts.

February 2025 - Security StackExchange

What the experts say
5Expert opinions

Spammer behavior is often arbitrary, where spamware may select a from/return path from a batch of addresses or rotate through sender addresses. Distinguishing between a planned attack and poorly written spam software requires analyzing a variety of sent emails. Using invalid 'To' and valid 'Return-Path' addresses is also a common technique in list bombing, allowing spammers to test and refine their targeting. There used to be companies such as Bounce.io that would sell advertising in bounce messages - showing its possible for spammers to exploit this.

Key opinions

  • Arbitrary Spam Behavior: Spam software may randomly select from/return paths, indicating unpredictable behavior.
  • Address Rotation: Spammers may rotate through sender addresses to evade detection.
  • Software vs. Strategy: Differentiating between spammer intent and software errors requires analysis of multiple emails.
  • List Bombing: Invalid 'To' addresses used for testing and refining target lists.
  • Bounce Advertising: Bounce messages are sometimes used for advertising.

Key considerations

  • Analyze Email Variety: A decent variety of emails are needed to distinguish spammer intent from software errors.
  • Monitor Sender Reputation: Continuously monitor sender reputation to detect potential abuse.
  • Implement Robust Filters: Implement robust spam filters to identify and block malicious emails.
  • Track bounceback messages: It's possible that bounceback messages are used for advertisement.
Expert view

Expert from Email Geeks shares that spammer behavior can be arbitrary and spamware often selects a from/return path from a batch of addresses when sending spam.

May 2022 - Email Geeks
Expert view

Expert from Word to the Wise explains that using invalid 'To' and valid 'Return-Path' addresses is a technique often associated with list bombing. Spammers might use this to test a list, determining which email addresses are valid and which are not, allowing them to refine their targeting in future campaigns.

November 2021 - Word to the Wise
Expert view

Expert from Email Geeks shares how bounce.io used to sell advertising in bounce messages.

December 2023 - Email Geeks
Expert view

Expert from Email Geeks says it's difficult to distinguish between a spammer's cunning plan and poorly written spam software without a decent variety of the emails they're sending.

May 2023 - Email Geeks
Expert view

Expert from Email Geeks suggests spammers might rotate through sender addresses.

June 2022 - Email Geeks

What the documentation says
5Technical articles

Spammers exploit the use of invalid 'To' addresses with valid 'Return-Path' addresses to manipulate the SMTP envelope, hide their identity, and exploit vulnerabilities in email servers. This technique enables directory harvesting, allowing spammers to identify valid email addresses from bounce messages. Address spoofing is facilitated by creating confusion and bypassing security measures. Since invalid 'To' addresses violate email protocols, spammers create confusion to bypass security checks. This approach also circumvents standard sender verification systems, enhancing spam effectiveness by exploiting the limited scrutiny of 'To' address validity.

Key findings

  • SMTP Envelope Manipulation: Spammers manipulate 'To' and 'Return-Path' addresses within the SMTP envelope to hide their identity.
  • Directory Harvesting: Invalid 'To' addresses are used to identify valid email addresses through bounce messages.
  • Address Spoofing: The technique facilitates address spoofing, bypassing security measures.
  • Protocol Violation: Invalid 'To' addresses violate email protocols, creating confusion for security bypass.
  • Verification Bypass: Standard sender verification systems are bypassed due to less stringent checks on 'To' address validity.

Key considerations

  • Implement Robust Verification: Enforce rigorous verification of both 'From' and 'To' addresses to prevent spoofing.
  • Monitor Bounce Messages: Analyze bounce messages for suspicious patterns indicative of directory harvesting.
  • Adhere to Email Protocols: Ensure strict adherence to email protocols to prevent malformed addresses.
  • Enhance Server Security: Strengthen email server security measures to mitigate exploitation of vulnerabilities.
Technical article

Documentation from Cisco Talos shares that this practice allows for bypassing standard email sender verification systems, which are usually configured to ensure the "From" address is not spoofed, but often do not check the validity of "To" addresses to the same extent. By bypassing this check, spammers can increase effectiveness.

January 2023 - Cisco Talos
Technical article

Documentation from Microsoft explains the described technique allows for address spoofing. It shares that by using a valid return path and invalid To addresses a spammer can cause confusion and potentially bypass some security measures.

March 2021 - Microsoft
Technical article

Documentation from IETF explains that invalid "To" addresses are not compliant with email protocols. Spammers exploit this by utilizing malformed addresses to create confusion in email systems, which can then be used to bypass security checks.

July 2021 - IETF
Technical article

Documentation from Mimecast explains that the technique described could be a form of directory harvesting. By sending emails to a range of invalid addresses, spammers can identify valid email addresses when they receive bounce messages, indicating that the mailbox exists.

November 2021 - Mimecast
Technical article

Documentation from RFC Editor answers that the 'Return-Path' (MAIL FROM) and 'To' (RCPT TO) addresses are part of the SMTP envelope, which dictates how the email is delivered. Spammers might manipulate these addresses to hide their identity or to exploit vulnerabilities in email servers.

December 2024 - RFC Editor