Suped

Summary

A DKIM permerror, particularly a 'bad signature' indication exclusively on Yahoo Mail, points to a fundamental failure in the email's cryptographic signature verification. This issue frequently arises not from a generalized DKIM setup problem, but from Yahoo Mail's notably stringent and sensitive validation process. Unlike other email providers, Yahoo's robust parsers are highly attuned to even minor alterations, non-standard formatting, or subtle discrepancies in an email's headers or body after the DKIM signature has been applied. Common culprits include modifications introduced by intermediate servers, such as email forwarding services or mailing lists, which invalidate the original signature without re-signing. Furthermore, Yahoo's strictness extends to precise canonicalization, meaning variations in line endings, extra whitespace, or header order can lead to rejection. Errors within the DKIM DNS TXT record itself, like incorrect public keys, are also more likely to be caught by Yahoo's detailed checks. Ultimately, this 'bad sig' often signifies that the message content or headers do not cryptographically match the original signature, an issue Yahoo is uniquely positioned to detect and enforce due to its advanced DMARC policies.

Key findings

  • Yahoo's Stricter Validation: Yahoo Mail employs a significantly more sensitive and stringent DKIM validation process compared to many other email providers. Its parsers are designed to detect even minor alterations, non-standard formatting, or subtle discrepancies that less strict services might overlook.
  • Post-Signing Content Alteration: The most frequent cause for a DKIM 'permerror (bad sig)' exclusively on Yahoo is modifications made to the email's headers or body by an intermediate server, such as an email forwarding service or a mailing list, after the initial DKIM signature has been applied, without subsequent re-signing.
  • Canonicalization and Formatting Sensitivity: Yahoo is particularly strict about canonicalization, meaning variations in line endings, extra whitespace, or the precise order of headers can invalidate a DKIM signature, even if the primary content remains untouched.
  • DNS Record Precision Matters: Subtle errors within the DKIM DNS TXT record itself, such as an incorrectly copied public key or extraneous characters, are more likely to be flagged by Yahoo's stringent parser than by other, more forgiving mail services.
  • DMARC Enforcement Impact: As a strong enforcer of DMARC policies, Yahoo Mail's strictness means that a failed DKIM signature-even due to minor alterations-often results in the email being rejected or sent to the spam folder for non-alignment with DMARC requirements.

Key considerations

  • Examine Intermediate Servers: Investigate whether email forwarding services or mailing lists are altering email headers or body content after the original DKIM signature has been applied. Yahoo's stringent validation will detect these post-signing modifications, invalidating the signature.
  • Verify DNS Records: Meticulously check your DKIM DNS TXT record for any subtle errors, such as incorrectly copied public keys, extraneous characters, or incorrect spacing, as Yahoo's parser is highly sensitive to these imperfections. Also, ensure DNS TTLs are at least 300 seconds, ideally around 3600 seconds, especially after changes.
  • Assess Canonicalization: Ensure your email sending system's canonicalization method (e.g., relaxed/simple) for headers and body content aligns precisely with what Yahoo Mail expects. Even slight discrepancies like variations in line endings, extra whitespace, or header order can cause a 'bad sig' error.
  • Review Header Inclusion: Confirm that all headers, particularly any new or modified ones introduced by intermediate systems, are explicitly included in the DKIM signature's 'h=' tag. Yahoo's robust validation processes will fail signatures if these headers are not accounted for.
  • Gather Diagnostic Data: To aid in diagnosis, collect and compare exact mail headers, including authentication results, from messages received on both Yahoo Mail and other services like Gmail. This can highlight discrepancies in how different providers process the email.

What email marketers say

9 marketer opinions

When a DKIM permerror, specifically a 'bad signature' status, appears exclusively for emails sent to Yahoo Mail, it signals a particular challenge with Yahoo's highly stringent authentication protocols. Unlike many other email providers, Yahoo's systems, underpinned by robust DMARC enforcement, are engineered to detect even the slightest alterations or formatting deviations in an email after its DKIM signature has been applied. This heightened sensitivity often means issues arise from changes introduced by intermediary services like forwarding systems or mailing lists, which inadvertently invalidate the original signature without re-signing the message. Furthermore, Yahoo's validation is notoriously strict about canonicalization, where variations in elements such as line endings, whitespace, or header order can lead to a rejected signature. Even subtle imperfections in the DKIM DNS TXT record itself, or headers not explicitly covered by the signature, are more readily identified and flagged by Yahoo, resulting in delivery failures.

Key opinions

  • Yahoo's Enhanced Sensitivity: Yahoo Mail's validation process is exceptionally rigorous, designed to catch minor alterations and non-standard formatting that less strict email services might overlook, leading to a rejected signature.
  • Intermediate Server Alterations: A primary cause for DKIM failure on Yahoo is modifications to email headers or body content by an intermediate server, such as a forwarding service or mailing list, after the initial DKIM signature is applied, without subsequent re-signing.
  • Canonicalization Precision Demands: Yahoo is notably strict about email canonicalization, meaning subtle changes in line endings, extra whitespace, or the exact order of headers can invalidate a DKIM signature, even if the primary content remains unchanged.
  • DNS Record Imperfections: Even subtle errors in the DKIM DNS TXT record, such as incorrectly copied public keys or extraneous characters, are more likely to be identified and cause failures by Yahoo's stringent parser.
  • Unsigned Header Inclusions: A permerror can occur when intermediate systems add or modify headers that are not explicitly included in the DKIM signature's 'h=' tag, as Yahoo's validation will detect these discrepancies.
  • DNS TTL Influence: Rapid DNS TTLs (Time To Live) for DKIM records, especially during changes, can exacerbate issues, making it crucial for TXT records to have a minimum TTL of 300 seconds, ideally around 3600 seconds.

Key considerations

  • Investigate Email Path: Thoroughly examine the email's journey for any intermediate servers-like forwarding services or mailing lists-that might modify headers or body content after the initial DKIM signature is applied.
  • Meticulously Verify DNS Record: Carefully check your DKIM DNS TXT record for any inaccuracies, including public key correctness, extraneous characters, or incorrect spacing, as Yahoo's parser is highly sensitive.
  • Adjust DNS TTLs: Ensure that your DKIM DNS TXT record's Time To Live (TTL) is set to at least 300 seconds, preferably around 3600 seconds, especially after making any changes to the record.
  • Align Canonicalization Settings: Confirm that your email sending system's canonicalization method for headers and body content, such as 'relaxed' or 'simple', is perfectly aligned with Yahoo Mail's expectations to prevent subtle formatting issues from invalidating the signature.
  • Confirm Header Inclusion in Signature: Verify that all headers, particularly any new or modified ones introduced by intermediate systems, are explicitly listed in the DKIM signature's 'h=' tag.
  • Leverage Mail Headers for Debugging: Collect and compare exact mail headers, including authentication results, from messages delivered to both Yahoo and other providers like Gmail to identify specific discrepancies and aid in diagnosis.

Marketer view

Email marketer from Email Geeks explains that fast TTLs (Time To Live) for DNS records, especially when changing things, can aggravate DNS provider issues leading to DKIM failures, and recommends checking that DKIM TXT record TTLs are at least 300 seconds, ideally around 3600 seconds.

19 Nov 2023 - Email Geeks

Marketer view

Email marketer from Email Geeks suggests sharing exact mail headers, including authentication results, from both Yahoo and Gmail to help diagnose the DKIM issue.

18 Apr 2023 - Email Geeks

What the experts say

2 expert opinions

A DKIM 'permerror' with a 'bad signature' status, particularly when it appears only on Yahoo Mail, indicates that the email's cryptographic signature cannot be successfully verified. Fundamentally, this means the message was either altered after being signed by your Mail Transfer Agent (MTA) or signed incorrectly. While this issue is not exclusive to Yahoo, their stringent validation processes are highly effective at detecting even subtle discrepancies. This precision often highlights problems such as modifications to email headers or body content during transit, an incorrect signing key being used, or a mismatch between the published public key and the one used for signing, all of which invalidate the email's original integrity.

Key opinions

  • Post-Signing Alteration: The most common reason for a DKIM 'bad signature' is that the email's content or headers were modified during transit after the initial DKIM signature was applied.
  • Incorrect Signing Configuration: The sending Mail Transfer Agent (MTA) may be using an incorrect private key or an improper method for signing messages, leading to a signature that fails validation.
  • DNS Key Mismatch: A 'permerror' can result from a discrepancy between the public DKIM key published in the Domain Name System (DNS) and the private key used by the sending server for signing.
  • Yahoo's Enhanced Detection: Yahoo Mail's authentication systems are notably more stringent and sensitive, often pinpointing subtle signature validation failures or transit alterations that other email services might overlook.
  • Diagnostic Discrepancy: The observation that the DKIM 'bad sig' appears only on Yahoo Mail, while passing on services like Gmail or Hotmail, strongly suggests the root cause lies in how Yahoo processes or validates the email, or a nuanced issue that only their strictness exposes.

Key considerations

  • Identify Transit Alterations: Thoroughly examine the email's route for any intermediate systems, such as forwarding services or mailing lists, that might modify headers or body content after DKIM signing.
  • Confirm DKIM Key Synchronization: Verify that the private key used by your sending Mail Transfer Agent (MTA) for signing precisely matches the public key published in your domain's DNS TXT record.
  • Scrutinize DNS Record for Precision: Meticulously review your DKIM DNS TXT record for any inaccuracies, including typos, extraneous characters, or incorrect key values that could cause validation failures.
  • Evaluate Recent Infrastructure Changes: Investigate any recent modifications to your mail servers, DKIM keys, or DNS configurations that may have inadvertently caused the 'bad signature' errors on Yahoo.
  • Compare Authentication Results: Send test emails to major providers like Gmail, Hotmail, and Yahoo Mail, then analyze the authentication results from each to identify specific differences that Yahoo is flagging.

Expert view

Expert from Email Geeks responds by asking diagnostic questions, including whether there were DNS issues, recent changes to DKIM keys or mailservers, and if the same message passed on other services like Gmail or Hotmail.

6 Feb 2025 - Email Geeks

Expert view

Expert from Word to the Wise explains that a DKIM 'bad signature' or 'permerror' typically indicates that the message was altered in transit after being signed, or that incorrect signing practices were used by the sending Mail Transfer Agent (MTA). This can happen if headers or content are modified, the wrong key is used for signing, or there's a mismatch between the published DNS key and the signing key. While the observation of this error only on Yahoo Mail is not specifically addressed by the source, these general reasons are the root cause of such DKIM validation failures.

8 Aug 2024 - Word to the Wise

What the documentation says

5 technical articles

A DKIM 'permerror' indicating a 'bad signature' specifically with Yahoo Mail signifies a failure in verifying the email's cryptographic integrity, meaning the received message content or headers do not match what was originally signed. While the underlying issue is a failure to maintain the email's integrity, Yahoo Mail's verification process is exceptionally rigorous, often exposing subtle discrepancies that other mail providers might overlook. These discrepancies frequently stem from alterations occurring post-signing, incorrect DKIM record configurations, or strict adherence to canonicalization rules where even minor formatting variations can invalidate the signature. This issue, though not exclusive to Yahoo, is often brought to light by their meticulous validation and robust DMARC enforcement, which are highly effective at identifying authentication failures.

Key findings

  • Cryptographic Integrity Failure: A 'bad sig' fundamentally means the email's cryptographic signature verification failed, indicating that the signed content (headers or body) does not match the received content, implying an alteration or incorrect signing.
  • Yahoo's Enhanced Scrutiny: Yahoo Mail employs an exceptionally rigorous validation process, consistently identifying subtle alterations, configuration errors, or formatting discrepancies that other, less stringent mail services might overlook.
  • Post-Signing Modifications: A common reason for a DKIM 'permerror (bad sig)' is modifications made to email content or headers by intermediate servers, such as forwarding services, after the DKIM signature has been applied, without subsequent re-signing.
  • Precise DNS Record Requirements: Incorrectly configured DKIM DNS records, including public keys with extra characters or typos, are more readily flagged by Yahoo's precise parsers, leading to a permanent failure.
  • Canonicalization Sensitivity: Yahoo Mail is highly sensitive to the canonicalization method specified in the DKIM signature. Even minor variations in whitespace, line endings, or header order can invalidate a signature that otherwise appears correct.

Key considerations

  • Verify DNS Record Accuracy: Meticulously check your DKIM DNS TXT record for any errors, including incorrect public keys, extraneous characters, or formatting issues, as Yahoo's parser is highly sensitive to these details.
  • Inspect for Transit Alterations: Identify any intermediate servers, such as email forwarding services or mailing lists, that might modify email headers or body content after the initial DKIM signature has been applied. These post-signing changes often trigger a 'bad sig' error on Yahoo.
  • Align Canonicalization Methods: Ensure your email sending system's canonicalization method (e.g., relaxed/simple for headers and body) is properly configured and compatible with Yahoo Mail's strict expectations regarding whitespace, line endings, and header order.
  • Compare Signed vs. Received Content: Utilize raw email source analysis to identify differences between the content originally signed and the content received by Yahoo. This helps pinpoint where alterations or discrepancies are occurring.
  • Test with DKIM Validators: Use online DKIM validation tools to get detailed reports on your DKIM signature. These tools can often reveal subtle issues related to key mismatches or canonicalization that Yahoo's stringent checks are detecting.

Technical article

Documentation from Postmark explains that a DKIM permerror (bad sig) often occurs when the email content or headers are altered after the DKIM signature is applied, or if there's a mismatch between the public key in the DNS record and the private key used for signing. These issues can be more apparent with stricter DMARC policies or stricter parsers like Yahoo's, which meticulously validate signatures.

12 Jul 2023 - Postmark

Technical article

Documentation from SendGrid explains that a DKIM permerror (bad sig) can be caused by an incorrectly configured DKIM record in DNS, such as a copied/pasted key with extra characters, or by modifications to the email message's headers or body by an intermediate server before it reaches the recipient, which invalidates the original signature. Yahoo's stringent validation often highlights these issues.

29 Oct 2021 - SendGrid

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