Why are DKIM validations failing intermittently with Office365?

Summary

Intermittent DKIM validation failures in Office 365 can be attributed to a multitude of factors ranging from DNS inconsistencies and misconfigurations to email body modifications and underlying infrastructure issues. Specifically, having differing DKIM keys across DNS servers, delays in DNS propagation, or incorrect DKIM signing settings within Office 365 are frequent causes. Furthermore, alterations to the email body during transit and issues with SPF/DMARC alignment can indirectly lead to DKIM failures. Problems with character encoding, outdated DNS setups, conflicting CNAME records, key rotation issues, and problematic server hops also contribute to this issue. Enabling DKIM may unearth pre-existing sending infrastructure problems. The DNS record should be audited for typos, and it is essential to investigate transit issues between hops.

Key findings

  • DNS Configuration: DNS record inconsistencies, propagation delays, and multiple DNS servers with differing DKIM keys cause validation failures.
  • Office 365 Settings: Incorrect DKIM signing policies within Office 365 lead to intermittent failures.
  • Email Modification: Email content alteration during transit by middle servers corrupts DKIM signatures.
  • SPF/DMARC: Misconfigured SPF and DMARC policies can indirectly cause DKIM failures.
  • Encoding Issues: Character encoding problems within the email body corrupt DKIM signatures.
  • Outdated DNS: Outdated DNS setups fail to update DKIM records automatically.
  • CNAME Conflicts: Conflicting CNAME records for the same host cause DKIM validation problems.
  • Key Rotation: Issues with key rotation necessitate verifying the current key's validity.
  • Server Hops: Investigating server hops can identify problematic intermediaries.
  • Infrastructure Issues: Enabling DKIM can reveal underlying problems within the email sending infrastructure.
  • Human Error: Simple human errors such as typos in DNS records can be the main reason for failure.

Key considerations

  • Synchronize DNS: Ensure DKIM records are consistent and fully propagated across all DNS servers.
  • Verify O365 Settings: Double-check DKIM signing policies within Office 365 for correct domains and users.
  • Audit Mail Flow: Investigate mail flow for content-altering intermediaries.
  • Align SPF/DMARC: Ensure SPF and DMARC policies align with DKIM settings.
  • Test Encoding: Regularly test emails for encoding-related problems.
  • Automate DNS Updates: Implement automated DKIM DNS updates.
  • Review CNAME Records: Verify no conflicting CNAME records exist.
  • Maintain Keys: Regularly rotate and update DKIM keys.
  • Track Server Hops: Implement tools to track and analyze server hops.
  • Audit DNS Records: Ensure all DNS records are validated and error free.
  • Address Underlying Issues: Evaluate sending infrastructure for pre-existing problems.

What email marketers say
7Marketer opinions

Intermittent DKIM validation failures with Office 365 can stem from various sources. DNS propagation delays or misconfigurations in SPF alignment, DMARC policies, or DNS settings can lead to DKIM failures. Email content issues like character encoding problems can corrupt signatures. Outdated DNS setups, conflicting CNAME records, key rotation issues, and problems in email server hops can also contribute to these intermittent failures.

Key opinions

  • DNS Propagation: DNS propagation delays often cause intermittent DKIM issues, so verifying records with online tools is essential.
  • SPF/DMARC: SPF alignment and DMARC policies can indirectly affect DKIM validation; misconfigurations can lead to failures.
  • Character Encoding: Problems with character encoding in email content can corrupt DKIM signatures, causing validation failures.
  • Outdated DNS: Old DNS setups might not automatically update DKIM records, requiring configuration verification.
  • CNAME Conflicts: Other CNAME records for the same host can conflict and cause DKIM validation to fail.
  • Key Rotation: Issues related to key rotation should be investigated by verifying that the key is up to date.
  • Server Hops: Analyzing the email's server hops can help identify points of failure in DKIM validation.

Key considerations

  • Monitor DNS: Continuously monitor DNS records for correct propagation and configuration to prevent intermittent issues.
  • Review Policies: Regularly review SPF and DMARC policies to ensure they align with DKIM settings and prevent unexpected failures.
  • Test Emails: Regularly test emails with different character sets and content to identify encoding-related problems.
  • Automate DNS Updates: Ensure DNS updates for DKIM are automated to prevent issues from outdated records.
  • Check CNAMEs: Verify that there are no conflicting CNAME records set for the same host as your DKIM record.
  • Update Keys: Always ensure that DKIM keys are up-to-date and properly rotated to maintain email authentication.
  • Analyse Server Hops: Implement tools to track and analyze server hops to identify any intermediaries causing DKIM validation failures.
Marketer view

Email marketer from StackExchange suggests that one way to find the issue is to investigate all the server hops that the mail passes through.

November 2021 - StackExchange
Marketer view

Email marketer from StackExchange responds that there could be issues relating to key rotation so you should verify the key is up to date.

April 2022 - StackExchange
Marketer view

Email marketer from SparkPost explains that problems with character encoding or unsupported characters in the email body can cause DKIM verification to fail, as it corrupts the signature. Always test email sending to diagnose this issue.

April 2024 - SparkPost
Marketer view

Email marketer from Reddit responds that old DNS setups might be failing to automatically update the DKIM records, and suggests checking the setup process to ensure that it is automated correctly.

September 2021 - Reddit
Marketer view

Email marketer from EasyDMARC shares that issues with SPF alignment can sometimes indirectly cause DKIM failures. While DKIM itself might be configured correctly, DMARC policies can lead to failure if SPF records are misconfigured.

May 2022 - EasyDMARC
Marketer view

Email marketer from StackExchange suggests ensuring there are no other CNAME records set for the same host, as this can cause problems.

August 2023 - StackExchange
Marketer view

Email marketer from ValMail explains that DNS propagation delays can result in intermittent DKIM validation failures. It is important to verify DNS records using online tools and ensure that the correct DKIM TXT record is published and fully propagated.

May 2024 - ValMail

What the experts say
5Expert opinions

Intermittent DKIM failures in Office 365 can stem from a combination of DNS issues, message modification in transit, and underlying sending infrastructure problems. DNS inconsistencies, such as having servers with different DKIM keys or general DNS propagation delays, are frequent culprits. Modifications to the email body during transit can invalidate the DKIM signature. Enabling DKIM can expose previously unnoticed issues within the sending setup. While the 'n' tag in a DKIM CNAME record isn't directly related to validation, DNS record problems such as typos or propagation issues are major contributors to DKIM problems.

Key opinions

  • DNS Inconsistencies: Having multiple DNS servers with differing DKIM keys is a common cause of intermittent failures.
  • Message Modification: Alterations to the email body during transit can invalidate the DKIM signature.
  • Underlying Issues: Enabling DKIM can reveal pre-existing problems in sending practices or infrastructure.
  • DNS Records: DNS Record issues and propagation problems are major contributors to DKIM problems.
  • CNAME 'n' Tag: The 'n' tag in a DKIM CNAME record is for human-readable notes and does not affect validation.

Key considerations

  • Check DNS Servers: Ensure all DNS servers have the same, valid DKIM key and that changes are fully propagated.
  • Investigate Transit: Examine the email path for any intermediaries that might be modifying the message content.
  • Review Infrastructure: Assess the sending infrastructure for underlying issues that DKIM might expose.
  • Audit DNS Records: Audit and check your DNS records, ensure there are no typos and there are no propagation issues.
Expert view

Expert from Spam Resource explains that a very common cause of DKIM problems are DNS record problems. These include: not waiting long enough after the DNS change, typo's in the records or DNS servers having issues.

June 2024 - Spam Resource
Expert view

Expert from Email Geeks explains that the 'n' tag in a DKIM CNAME record is for human-readable notes and is not used in the validation process.

March 2023 - Email Geeks
Expert view

Expert from Email Geeks shares that if DKIM validation fails for only some emails, the issue is more likely related to the mail body being modified in transit, rather than the DKIM key itself.

June 2021 - Email Geeks
Expert view

Expert from Email Geeks explains that failing close to 50% of DKIM validation often indicates a DNS issue, such as having two DNS servers, one with a valid key and one without.

September 2022 - Email Geeks
Expert view

Expert from Word to the Wise explains that sometimes enabling DKIM can expose existing issues with your sending practices or infrastructure, leading to increased visibility of failures that were previously masked. These can include inconsistent DNS records or email content manipulation.

May 2021 - Word to the Wise

What the documentation says
3Technical articles

According to Microsoft documentation, intermittent DKIM validation failures in Office 365 can arise from three primary issues: inconsistencies or delays in DNS record propagation, incorrect configuration of DKIM signing settings within Office 365, and alteration of email content during transit. Ensuring DNS records are fully propagated and consistent across servers, verifying the correct DKIM signing policy is enabled for the relevant domains and users, and investigating potential mail flow issues or third-party programs altering email content are crucial for resolving these failures.

Key findings

  • DNS Issues: Inconsistent DNS records or propagation delays lead to intermittent DKIM failures.
  • Misconfiguration: Incorrect DKIM signing settings within Office 365 cause validation problems.
  • Content Alteration: Email content modifications in transit by middle servers invalidate DKIM signatures.

Key considerations

  • Verify DNS: Ensure DKIM records are fully propagated across all DNS servers.
  • Check Settings: Double-check the DKIM signing policy and enable it for correct domains and users.
  • Investigate Mail Flow: Investigate potential mail flow issues or third-party programs altering email content.
Technical article

Documentation from Microsoft Docs explains that intermittent DKIM failures can occur if there are inconsistencies or propagation delays in your DNS records. Ensure that your DKIM records have fully propagated across all DNS servers.

July 2022 - Microsoft Docs
Technical article

Documentation from Microsoft Docs shares that one common cause of intermittent failures is incorrect configuration of the DKIM signing settings within Office 365. Double-check the signing policy and ensure it is enabled for the correct domains and users.

July 2022 - Microsoft Docs
Technical article

Documentation from Microsoft Docs explains that DKIM failures happen intermittently if email content is altered in transit by a middle server. This alteration invalidates the DKIM signature, so it is necessary to investigate any potential mail flow issues, or ensure that email is not being altered by third-party programs.

September 2024 - Microsoft Docs