How to fix DKIM failing due to apostrophe in From header at ATT.net?

Summary

To resolve DKIM failures caused by apostrophes in the From header at ATT.net, experts, marketers, and documentation sources converge on several key recommendations. The root cause is often an invalid From header that ATT.net attempts to correct, breaking the DKIM signature. Solutions include ensuring valid From headers by quoting display names (especially those with special characters or spaces), verifying UTF-8 encoding, and maintaining RFC compliance. Additionally, testing email rendering across various clients, monitoring DMARC reports, and simplifying headers are crucial. Understanding that some email providers have unique parsing rules is essential for achieving consistent deliverability.

Key findings

  • Invalid From Headers: The primary cause is an invalid From header that ATT.net modifies, leading to DKIM failure.
  • Quoting Display Names: Using double quotes around display names with apostrophes or spaces resolves the issue and ensures compatibility.
  • RFC Compliance: Adhering to RFC specifications for From header formatting is crucial.
  • Email Encoding: Ensuring UTF-8 encoding and declaring it in headers prevents character-related issues.
  • DKIM Alignment: Proper DKIM alignment is necessary for DMARC compliance, especially with strict policies (p=reject).

Key considerations

  • Provider-Specific Quirks: Different email providers have unique parsing rules; account for provider-specific behaviors.
  • Testing Across Clients: Test email rendering and DKIM validation across various email clients and providers.
  • Header Simplification: Keep email headers as simple and standard as possible to prevent parsing issues.
  • DMARC Monitoring: Monitor DMARC reports to identify and address DKIM failures promptly.
  • Proactive Approach: Implement proactive measures, such as always quoting display names with special characters, to prevent issues before they arise.

What email marketers say
8Marketer opinions

To resolve DKIM failures caused by apostrophes in the From header at ATT.net, various email marketers recommend ensuring proper character encoding (UTF-8), double-quoting the display name, testing email rendering across different clients, maintaining a clean email list, simplifying headers, analyzing bounce codes, adhering to RFC specifications, and testing with multiple providers. Addressing provider-specific quirks is also essential.

Key opinions

  • Character Encoding: Using UTF-8 encoding and declaring it in the headers can resolve issues related to special characters.
  • Double Quoting: Double-quoting the display name in the From header, especially with apostrophes or spaces, ensures compatibility.
  • Testing: Testing email rendering across various clients identifies inconsistencies and display problems.
  • Email Authentication: Proper setup of SPF, DKIM, and DMARC is crucial for email authentication and deliverability.
  • Simple Headers: Keeping email headers simple and standard helps avoid issues with different email providers.
  • Bounce Codes: Analyzing bounce codes and error messages provides insights into the cause of DKIM failures.
  • RFC Compliance: Ensuring the From header adheres to RFC specifications prevents validation issues.

Key considerations

  • Provider Quirks: Different email providers have unique parsing rules, so account for provider-specific quirks.
  • Deliverability: Maintain a clean email list and avoid spam triggers to improve overall deliverability.
  • Testing: Testing email rendering using available tools before sending mass emails is important.
  • Multiple Providers: Testing sending setup with multiple providers to determine compatibility.
Marketer view

Email marketer from EmailGeek explains that you need to ensure the header doesn't violate RFC specifications or mailbox provider requirements

April 2021 - EmailGeek
Marketer view

Email marketer from Litmus recommends using email testing tools to preview emails across different email clients and identify rendering issues. Since From headers can be interpreted differently, testing can reveal whether the apostrophe is causing display problems or DKIM failures.

June 2023 - Litmus
Marketer view

Email marketer from Email Marketing Tips suggests checking the bounce codes and error messages provided by the receiving mail server. These messages often contain detailed information about why the email was rejected, which can help diagnose the cause of the DKIM failure.

March 2022 - Email Marketing Tips
Marketer view

Email marketer from Reddit recommends double-quoting the entire display name in the From header, especially when it contains apostrophes or spaces, to ensure compatibility across different email providers and prevent DMARC failures. This is a common practice to avoid parsing issues.

January 2024 - Reddit
Marketer view

Email marketer from Stack Overflow suggests that the issue is with character encoding. They suggest ensuring the email is encoded with UTF-8 and the headers declare this encoding.

December 2022 - Stack Overflow
Marketer view

Email marketer from Email on Acid recommends testing email rendering across various email clients and providers, as inconsistencies in how they interpret From headers can lead to deliverability problems. They suggest using tools to preview how the email will appear and adjust the From header accordingly.

May 2022 - Email on Acid
Marketer view

Email marketer from Mailjet states that ensuring proper email authentication setup (SPF, DKIM, DMARC) is crucial, but also highlights the importance of cleaning email lists and avoiding spam trigger words to maintain a good sender reputation and improve deliverability.

April 2023 - Mailjet
Marketer view

Email marketer from SuperUser shares that some email providers have quirks in how they handle email headers. They recommend keeping the headers as simple and standard as possible, which includes quoting display names with special characters.

April 2021 - SuperUser

What the experts say
6Expert opinions

Experts agree that DKIM failures due to apostrophes in the From header at ATT.net are caused by invalid headers that ATT.net attempts to correct, breaking the DKIM signature. The recommended solutions involve ensuring valid From headers by quoting the display name, especially when it contains special characters like apostrophes. Testing with multiple providers and maintaining RFC compliance is also suggested.

Key opinions

  • Invalid Headers: The root cause is an invalid From header.
  • Quoting: Quoting the display name, especially with special characters, resolves the issue.
  • ATT.net Correction: ATT.net's attempt to fix the invalid header breaks the DKIM signature.
  • RFC Compliance: Adhering to RFC specifications ensures compatibility.

Key considerations

  • Testing: Test sending setup with multiple email providers.
  • Header Simplicity: Keep email headers simple and standards-compliant.
  • Proactive Quoting: Quote all display names with unusual characters to avoid issues.
Expert view

Expert from Word to the Wise recommends keeping email headers as simple and standards-compliant as possible. They suggest using double quotes around display names that contain special characters like apostrophes to avoid issues with email providers that may have different parsing rules.

August 2022 - Word to the Wise
Expert view

Expert from SpamResource suggests testing the sending setup with multiple email providers. Check if the DKIM signature is valid and the From header is correctly formatted. It is possible some providers have stricter RFC compliance than others.

November 2022 - SpamResource
Expert view

Expert from Email Geeks explains that the mail being sent has an invalid From: header. AT&T fixes it, which breaks the DKIM signature. The solution is to send a valid From: header, easily achieved by quoting the friendly from in double quotes.

September 2021 - Email Geeks
Expert view

Expert from Email Geeks suggests quoting or escaping the apostrophe in the From header to resolve the issue with AT&T.

June 2023 - Email Geeks
Expert view

Expert from Email Geeks recommends quoting anything with unusual characters in the From header, ideally quoting it all the time, to avoid grey areas and ensure compatibility.

December 2021 - Email Geeks
Expert view

Expert from Email Geeks confirms that invalid From headers are the root cause. AT&T's servers fix them, leading to DKIM failures when handed over to Yahoo. They suggest sending valid From headers.

July 2024 - Email Geeks

What the documentation says
4Technical articles

Documentation sources indicate that DKIM failures related to apostrophes in From headers at ATT.net arise from improper formatting. The core recommendation is to ensure RFC compliance by using quoted strings for display names containing special characters, as certain mail servers may not handle unquoted special characters correctly, even if technically valid. Proper DKIM alignment is crucial for DMARC compliance, and monitoring DMARC reports helps identify and address DKIM failures effectively.

Key findings

  • RFC Compliance: From headers must comply with RFC standards for proper formatting.
  • Quoted Strings: Using quoted strings for display names with special characters prevents validation failures.
  • DKIM Alignment: Proper DKIM alignment is essential for DMARC compliance.
  • DMARC Reports: Monitoring DMARC reports helps identify and address DKIM failures.

Key considerations

  • Character Handling: Sanitize or enclose special characters in quotes to avoid compatibility issues.
  • Stricter Policies: Strict DMARC policies (p=reject) can severely impact email delivery when DKIM fails.
  • Mail Server Variance: Be aware that different mail servers may have varying levels of RFC compliance.
Technical article

Documentation from ietf.org specifies that the display-name in the From header can be an atom or a quoted string. Apostrophes are valid within an atom but quoting is necessary when spaces or other special characters are present.

February 2023 - ietf.org
Technical article

Documentation from Port25 suggests ensuring that the From header is properly formatted and compliant with RFC standards. They recommend using quoted strings for display names containing special characters to prevent DKIM validation failures.

May 2022 - Port25
Technical article

Documentation from DKIM Wizard advises sanitizing the From header to remove or escape special characters, or enclose the display name in quotes. They suggest that while certain characters might be technically valid, they can cause issues with some mail servers.

July 2024 - DKIM Wizard
Technical article

Documentation from DMARC.org explains the importance of DKIM alignment for DMARC compliance and provides insights into how strict DMARC policies (like p=reject) can affect email delivery when DKIM fails. They suggest carefully monitoring DMARC reports to identify and address DKIM failures.

February 2024 - dmarc.org