How do I fix Apple Mail DMARC failure when sending from Gmail with a non-Gmail domain?

Summary

DMARC failures when sending emails from Apple Mail, using a Gmail account with a non-Gmail domain, are often due to authentication mismatches and misconfigurations. Experts, marketers, and documentation sources agree that properly setting up SPF and DKIM records for your domain is crucial. A key problem is when Gmail rewrites the message or when Apple Mail uses the personal Gmail account settings instead of the Google Workspace account settings for the domain. The 'From' address must align with the authenticated sending domain, or the email infrastructure used must be authorized by the domain's owners. Additionally, understanding DMARC basics, configuring Gmail to send with a custom 'From' address, and ensuring Apple Mail uses the correct outgoing SMTP server are vital steps to resolve this issue and prevent email spoofing.

Key findings

  • Authentication Mismatch: Sending from Gmail with a non-Gmail 'From' address causes DMARC failures due to authentication mismatches.
  • SPF & DKIM Configuration: Properly configured SPF and DKIM records for your domain in Google Workspace are essential.
  • Gmail Rewriting: Gmail can rewrite messages, leading to DMARC failures, even when a different 'From' address is set.
  • Apple Mail Settings: Incorrect Apple Mail settings, such as using a personal Gmail account instead of the Workspace account, contribute to failures.
  • Correct Server Usage: Apple Mail needs to use the correct outgoing SMTP server, configured with the right credentials, for the custom domain.

Key considerations

  • Align 'From' Address: Align the 'From' address with the authenticated sending domain or use a domain authorized to send email through Gmail.
  • Use Domain's SMTP Server: Consider using your domain's SMTP server directly with proper SPF/DKIM setup to avoid Gmail's rewriting issues.
  • Configure SPF Record: Add Google's SPF record to authorize sending emails on behalf of your domain to prevent them from being marked as spam.
  • Monitor DMARC Reports: Pay attention to DMARC reports to track authentication failures and adjust configurations accordingly.
  • Understand DMARC Policy: Familiarize yourself with DMARC policies and how email receivers should handle messages failing authentication checks.

What email marketers say
11Marketer opinions

When sending emails from Apple Mail using a Gmail account with a 'From' address of a non-Gmail domain, DMARC failures often occur due to authentication mismatches. Several solutions address this issue: ensuring correct SMTP server and credential configuration within Apple Mail; properly setting up SPF and DKIM records for the domain in Google Workspace; matching the 'From' address with the Gmail account or authorized domain; and utilizing the domain's mail server directly instead of Gmail's SMTP relay. Correctly configuring 'Send mail as' settings in Gmail/Google Workspace and understanding DMARC basics are also critical.

Key opinions

  • SMTP Configuration: Incorrect SMTP server settings in Apple Mail can cause authentication issues.
  • SPF/DKIM Records: Properly configured SPF and DKIM records are essential for DMARC compliance.
  • From Address: The 'From' address must align with the sending Gmail account or authorized domain.
  • Google Workspace Setup: Correctly configuring 'Send mail as' settings in Google Workspace is crucial.
  • DMARC Basics: A foundational understanding of DMARC principles is necessary for troubleshooting.

Key considerations

  • Account Credentials: Verify that the Apple Mail account is set up with the correct Google Workspace credentials.
  • Authentication Alignment: Ensure the domain used in the 'From' address is authenticated through SPF and DKIM.
  • Gmail SMTP Relay: Consider the implications of using Gmail's SMTP relay and potential DMARC issues.
  • Domain Mail Server: Explore the option of sending emails directly from your domain's mail server.
  • Testing: After making changes, thoroughly test email sending to confirm DMARC compliance.
Marketer view

Email marketer from SparkPost details understanding the basics of DMARC is vital to ensure your email is not marked as spam and they recommend ensuring you set this up or configure your settings correctly.

January 2022 - SparkPost
Marketer view

Email marketer from Mailhardener responds that when using Gmail's SMTP relay to send emails with a different From: address, DMARC failures are likely. To resolve this, configure your domain's SPF and DKIM records correctly and ensure that the From: address aligns with the authenticated sending domain.

August 2023 - Mailhardener
Marketer view

Email marketer from Reddit answers that the problem is often caused by the user trying to send emails with a 'From' address that doesn't match the Gmail account. The recommended solution involves correctly configuring the 'Send mail as' setting in Gmail or Google Workspace to use the desired domain.

October 2022 - Reddit
Marketer view

Email marketer from StackOverflow responds to ensure you configure SPF records for all domains you use to send email and that you are using the domain of the account set up in Apple Mail to send emails.

August 2024 - StackOverflow
Marketer view

Email marketer from Email Geeks explains to ensure the workspace account is correctly set up in Apple Mail and the correct SMTP server and credentials actually work and if Apple Mail has a problem sending emails via the accounts SMTP server, it asks to use a different server.

January 2025 - Email Geeks
Marketer view

Email marketer from Email Geeks shares that the outbound for the account had defaulted to Gmail and to fix it, toggle the drop down to the right outbound account for the email address.

December 2021 - Email Geeks
Marketer view

Email marketer from MXToolbox explains that DMARC relies on both SPF and DKIM for authentication. Ensure your SPF record is correctly configured to authorize Gmail to send emails on behalf of your domain.

March 2023 - MXToolbox
Marketer view

Email marketer from Litmus answers that ensuring both SPF and DKIM records are properly set up for your domain and also that the domain in the 'From' header matches what you are authenticating with is vital to ensure your emails are not marked as spam.

September 2022 - Litmus
Marketer view

Email marketer from StackExchange shares that when using Gmail SMTP servers to send emails, if the email isn't correctly authenticated with SPF/DKIM for the domain in the 'From:' address, it's likely to trigger a DMARC failure. One workaround includes configuring Google Workspace to send as the domain or sending directly from the domain's mail server.

June 2024 - StackExchange
Marketer view

Email marketer from EmailOnAcid explains that to resolve DMARC issues, setting up DKIM (DomainKeys Identified Mail) is crucial. DKIM adds a digital signature to your outgoing emails, which verifies that the email was sent and authorized by the owner of the domain and gives clear steps on how to do this.

February 2022 - EmailOnAcid
Marketer view

Email marketer from Super User Forum shares that ensuring both SPF and DKIM records are properly set up for your domain in Google Workspace is essential and failing to do this will most likely result in emails failing the DMARC test.

September 2023 - Super User Forum

What the experts say
7Expert opinions

DMARC failures when using Apple Mail to send from a Gmail account with a non-Gmail domain often stem from misconfigurations and authentication issues. Sending mail from Gmail with a different 'From' address can trigger DMARC failures because Gmail might rewrite the message, causing authentication discrepancies. A key issue is the need to use mail infrastructure owned or approved by the domain in the 'From' address. Apple Mail, being a mail client, requires a properly configured outbound server to sign with the correct DKIM. The Google Workspace account associated with the domain may not be set up to sign with DKIM, and Apple Mail might be configured to use a personal Gmail account instead of the Workspace account. Ensuring SPF and DKIM records are correctly configured and aligning the 'From' address with a domain authorized to send email through Gmail or using your own domain's SMTP server are vital steps for resolving this.

Key opinions

  • DMARC Failure Causes: Sending from Gmail with a non-Gmail domain in the 'From' header can cause DMARC to fail.
  • Infrastructure Ownership: You must use mail infrastructure approved by the owners of the domain in the 'From' address.
  • DKIM Configuration: The Google Workspace account may not be configured to sign with DKIM.
  • Apple Mail Configuration: Apple Mail might be configured to use a personal Gmail account instead of the Workspace account.
  • Outbound Server Configuration: Apple Mail needs a properly configured outbound server to sign with the correct DKIM.

Key considerations

  • SPF and DKIM Records: Ensure your domain's SPF and DKIM records are correctly configured.
  • From Address Alignment: Align the 'From' address with a domain authorized to send email through Gmail.
  • Own SMTP Server: Consider using your own domain's SMTP server with proper SPF/DKIM setup.
  • Apple Mail Settings: Verify that Apple Mail is using the correct outgoing SMTP server for your custom domain.
  • Account Selection: Ensure you're sending through the correct account in apple mail and not sending from a seperate Gmail that is rewriting your outbound emails.
Expert view

Expert from Email Geeks shares that Apple Mail is a mail client, not a mail server, and needs an outbound server to send mail and the outbound server isn’t configured to sign with cooalliance.com DKIM.

September 2024 - Email Geeks
Expert view

Expert from Email Geeks shares that one cannot use a cooalliance.com email address unless they are using mail infrastructure owned or approved by the owners of cooalliance.com to send mail.

March 2024 - Email Geeks
Expert view

Expert from Email Geeks explains that it seems like Apple Mail is configured to send it from the user's personal Gmail account, not the Workspace account where the domain is configured and when connecting to Gmail to send from a mail client, Gmail overwrites the mail from with the Gmail user account credentials.

May 2024 - Email Geeks
Expert view

Expert from Spam Resource explains that if you send from a Gmail account (even if you set the 'From:' to a different address), Gmail will likely rewrite the message in a way that can cause DMARC failures. Using your own domain's SMTP server with proper SPF/DKIM setup is crucial to avoid this.

September 2021 - Spam Resource
Expert view

Expert from Email Geeks explains that sending mail from Gmail but using a non-Gmail domain in the From: header will cause DMARC to fail, as DMARC sees it as incorrect.

September 2024 - Email Geeks
Expert view

Expert from Email Geeks explains that the Google Workspace account may not be configured to sign with DKIM and questions if the user is trying to relay out through a Gmail account rather than the Workspace account.

August 2024 - Email Geeks
Expert view

Expert from Word to the Wise suggests that when experiencing DMARC failures while sending from Gmail with a non-Gmail domain, it's essential to ensure that your domain's SPF and DKIM records are correctly configured. It is crucial to align the 'From:' address with a domain authorized to send email through Gmail's servers. Also, verify that Apple Mail is using the correct outgoing SMTP server for your custom domain.

March 2022 - Word to the Wise

What the documentation says
5Technical articles

Documentation regarding DMARC failure when using Apple Mail and Gmail with a non-Gmail domain highlights several key points: Adding Google's SPF record to your domain is crucial to authorize Google to send emails on your behalf and prevent them from being marked as spam. DMARC, an email authentication protocol, enables domain owners to specify how email receivers should handle messages failing authentication checks (SPF and DKIM), combating spoofing and phishing. Apple Support details how to change outgoing mail server (SMTP) settings in Mail on Mac, emphasizing the need for the correct server from your email provider. DMARC, as per RFC 7489, builds upon SPF and DKIM to give domain owners tools against unauthorized email use. Google Workspace Admin Help provides steps to configure Gmail for sending emails with a custom 'From' address, requiring verification and permission to send on behalf of the domain.

Key findings

  • SPF Record Importance: Adding Google's SPF record is essential to authorize sending emails on behalf of your domain.
  • DMARC Protocol: DMARC allows domain owners to specify how to handle messages failing SPF and DKIM checks.
  • SMTP Settings: Using the correct outgoing mail server (SMTP) settings in Apple Mail is critical.
  • Custom 'From' Address Configuration: Google Workspace Admin Help provides steps to configure Gmail with custom 'From' addresses.
  • DMARC Evolution: DMARC builds upon SPF and DKIM technologies for email domain protection.

Key considerations

  • Email Spoofing: Implement SPF records to prevent email spoofing.
  • Authentication Failure Handling: Define how email receivers should handle authentication failures using DMARC.
  • Outgoing Mail Server: Use the correct SMTP server provided by your email service provider in Apple Mail.
  • Unauthorized Email Use: Utilize DMARC to protect against unauthorized use of your email addresses.
  • Domain Verification: Ensure you have permission and verify your custom 'From' address in Gmail.
Technical article

Documentation from Apple Support details the steps to change the outgoing mail server (SMTP) settings in Mail on Mac. It highlights the importance of using the correct server provided by your email service provider for sending mail.

October 2024 - Apple Support
Technical article

Documentation from Google Workspace Admin Help provides the steps to configure Gmail to send emails using a custom 'From' address. This involves adding the email address and verifying it, ensuring that you have permission to send emails on behalf of the domain.

January 2023 - Google Workspace Admin Help
Technical article

Documentation from Google Workspace Admin Help explains that to prevent email spoofing, add Google's SPF record to your domain. This authorizes Google to send email on behalf of your domain, helping to prevent messages from being marked as spam.

January 2022 - Google Workspace Admin Help
Technical article

Documentation from RFC Editor (RFC 7489) explains that DMARC builds on SPF and DKIM technologies to provide email domain owners with a mechanism to reduce the threat of unauthorized use of their email addresses.

February 2022 - RFC Editor
Technical article

Documentation from DMARC.org explains that DMARC (Domain-based Message Authentication, Reporting & Conformance) is an email authentication protocol that allows domain owners to specify how email receivers should handle messages that fail authentication checks (SPF and DKIM). This helps prevent email spoofing and phishing attacks.

October 2024 - DMARC.org