Why are emails from Microsoft accounts being rejected by Gmail, and what is the role of IPv6?

Summary

Gmail's rejection of emails from Microsoft accounts is a multifaceted issue influenced by factors such as domain/IP reputation, IPv6 misconfigurations, aggressive spam filtering, and the exploitation of default DKIM domains. Documentation highlights the importance of adhering to email standards and best practices, while experts note that Gmail treats IPv6 reputation differently and holds it to higher standards. To improve deliverability, it is crucial to monitor sender reputation, properly configure IPv6, ensure email authentication, and comply with sending policies.

Key findings

  • Reputation: Gmail rejects emails based on domain and IP reputation, often due to spam activity associated with Microsoft accounts or IP ranges.
  • IPv6: Improper IPv6 configuration and the use of shared IPv6 addresses significantly impact deliverability to Gmail due to stricter reputation checks.
  • Authentication: Lack of proper email authentication (SPF, DKIM, DMARC) results in emails being flagged as spam or rejected by Gmail.
  • Exploitation: Exploitation of default DKIM domains in G Suite and O365 contributes to deliverability problems.
  • Filtering: Gmail's aggressive spam filtering mistakenly blocks legitimate emails from Microsoft accounts.

Key considerations

  • Monitor Reputation: Regularly monitor your IP and domain reputation using tools like Google Postmaster Tools and MXToolbox.
  • Configure IPv6: Ensure proper IPv6 configuration or revert to IPv4 if deliverability issues persist with IPv6.
  • Implement Authentication: Implement and verify SPF, DKIM, and DMARC records to authenticate your emails.
  • Review Sending Practices: Review and adhere to both Gmail's and Microsoft's sending policies to avoid being flagged as spam.
  • Dedicated IP: Consider using a dedicated IP address, especially for IPv6, to improve sender reputation.
  • Address Fundamental Issues: Tools like Return Path Certification can help but will not solve fundamental sending and list management problems.

What email marketers say
9Marketer opinions

Gmail's rejection of emails from Microsoft accounts is often attributed to domain and IP reputation issues, particularly when sending via IPv6. Aggressive spam filtering, shared IP addresses, and misconfigured IPv6 setups can lead to deliverability problems. Ensuring proper email authentication (SPF, DKIM, DMARC), monitoring sender reputation, and adhering to Gmail's and Microsoft's sending policies are crucial for improving email delivery rates. Google Postmaster Tools and MXToolbox can aid in diagnosing and resolving these issues.

Key opinions

  • Reputation: Gmail rejects emails from Microsoft accounts due to low domain or IP reputation, often linked to spam activity.
  • IPv6 Issues: Improperly configured IPv6 settings and shared IPv6 addresses can negatively impact deliverability to Gmail.
  • Spam Filtering: Gmail's aggressive spam filters may mistakenly block legitimate emails from Microsoft accounts.
  • Authentication: Lack of proper email authentication (SPF, DKIM, DMARC) can lead to email rejection by Gmail.

Key considerations

  • Check Blocked Status: Verify if your Outlook.com account or IP address is blocked by Gmail.
  • Authentication Setup: Implement and verify SPF, DKIM, and DMARC records to authenticate your emails.
  • Monitor Reputation: Regularly monitor your sender reputation using tools like Google Postmaster Tools and MXToolbox.
  • IPv6 Configuration: Ensure proper configuration of IPv6 settings, or consider using IPv4 if IPv6 deliverability is problematic.
  • Dedicated IP: Using a dedicated IP address, especially for IPv6, can improve deliverability.
  • Review Policies: Comply with both Gmail's and Microsoft's sending policies to avoid being flagged as spam.
Marketer view

Marketer from Email Geeks shares information about Google (Gmail) rejecting email from Microsoft accounts due to a "domain reputation issue." The issue was specific to Microsoft sending to Gmail via IPv6, with Google detecting these emails as spam to protect their end users. Both Google and Microsoft have acknowledged the issue, and the sender she worked with is now able to deliver to Gmail.

August 2024 - Email Geeks
Marketer view

Email marketer from Google Support explains that Gmail might reject emails if the sender is blocked or marked as spam. They advise checking the blocked senders list and ensuring that the sender isn't inadvertently marked as spam.

November 2023 - Google Support
Marketer view

Email marketer from Microsoft Support Forum responds that Gmail may reject emails from Outlook.com if the IP address or domain has a low reputation due to spam activity. They suggest checking if the Outlook.com account is blocked and reviewing Microsoft's policies to ensure compliance.

March 2021 - Microsoft Support Forum
Marketer view

Email marketer from StackExchange explains Gmail's spam filters may mark emails from Microsoft accounts as spam due to shared IP addresses and domain reputation. They suggest ensuring proper email authentication (SPF, DKIM, DMARC) is in place, and to monitor sender reputation.

March 2025 - StackExchange
Marketer view

Email marketer from Mailjet shares tips on improving email deliverability to Gmail, including using a dedicated IP address (especially for IPv6), monitoring sender reputation, and implementing proper authentication protocols. They recommend regularly checking Google Postmaster Tools for insights.

March 2021 - Mailjet
Marketer view

Email marketer from SparkPost Blog shares that IPv6 can introduce deliverability challenges if not properly configured. They highlight that many older email systems aren't fully compatible with IPv6, and poor IPv6 reputation can negatively impact delivery rates to Gmail.

October 2023 - SparkPost Blog
Marketer view

Email marketer from DNSQueries advises users to check their SPF (Sender Policy Framework) records to ensure that Microsoft's sending servers are authorized to send email on behalf of their domain. Incorrect or missing SPF records can lead to emails being rejected by Gmail.

May 2023 - DNSQueries
Marketer view

Email marketer from MXToolbox explains that poor IP reputation can cause email delivery problems. They recommend using their tools to check IP reputation against various blacklists and implementing email authentication protocols like SPF, DKIM, and DMARC.

December 2023 - MXToolbox
Marketer view

Email marketer from Reddit shares that Gmail's aggressive spam filtering can sometimes mistakenly block legitimate emails from Microsoft accounts. This is often due to shared IP addresses used by Microsoft, which can be affected by the behavior of other users. They recommend checking spam folders and contacting Gmail support.

June 2022 - Reddit

What the experts say
5Expert opinions

Experts indicate that Gmail's rejection of emails from Microsoft accounts, particularly those sent over IPv6, is often due to reputation differences between IPv4 and IPv6, infrastructure reputation issues, and the exploitation of default DKIM domains. Gmail holds IPv6 mail to higher standards, and Microsoft's IP ranges may suffer from a bad reputation due to spam. While tools like Return Path certification can assist with deliverability, fundamental sending practices must be addressed first.

Key opinions

  • IPv6 Reputation: Gmail treats IPv6 reputation differently than IPv4 reputation, requiring careful configuration and monitoring.
  • Infrastructure Reputation: Delivery problems from Microsoft or Google, and not elsewhere, often indicate an infrastructure reputation issue.
  • DKIM Exploitation: Exploitation of default DKIM domains in G Suite and O365 contributes to deliverability problems.
  • Higher Standards: Google holds mail over IPv6 to higher standards, contributing to potential rejection.

Key considerations

  • IPv6 Configuration: Carefully configure and monitor IPv6 settings to maintain a good reputation.
  • Address Sending Practices: Ensure proper email authentication, content quality, and list hygiene.
  • Avoid DKIM Exploitation: Do not exploit default DKIM domains to avoid damaging your own domain reputation.
  • Infrastructure Review: Review and improve your email infrastructure to maintain a positive sending reputation.
Expert view

Expert from Spamresource explains that Gmail treats IPv6 reputation differently than IPv4 reputation. Sending from a shared IPv6 address or with poor IPv6 setup can negatively impact deliverability to Gmail. While not impossible, sending email to Gmail over IPv6 requires careful configuration and monitoring.

August 2024 - Spamresource
Expert view

Expert from Word to the Wise explains that Return Path certification (now Validity) can help improve deliverability to Gmail and other providers, but doesn't solve fundamental sending issues. It acts more like a 'fast pass' once other deliverability issues (authentication, content, list hygiene) are properly addressed.

September 2023 - Word to the Wise
Expert view

Expert from Email Geeks suggests that the problem is made worse by people who exploit default DKIM domains/subdomains in G Suite and O365 to avoid damaging their own domain reputation while sending unwanted emails.

May 2022 - Email Geeks
Expert view

Expert from Email Geeks states that Google holds mail over IPv6 to higher standards and that Microsoft customers have sent so much spam to Google that their IP range has a bad reputation. If delivery problems exist from Microsoft or Google and not elsewhere, it is likely an infrastructure reputation problem.

February 2024 - Email Geeks
Expert view

Expert from Email Geeks explains that sending mail to Gmail over IPv6 can lead to problems if not done correctly. He shares a link to an article he published in 2020 about this issue and notes that Google seems to treat reputation differently on IPv6 versus IPv4.

March 2024 - Email Geeks

What the documentation says
5Technical articles

Email delivery issues from Microsoft accounts to Gmail are influenced by factors detailed in various documentation sources. While RFCs outline fundamental email protocols and message formatting standards, they don't specifically address IPv6 or Gmail's filtering mechanisms. Google Postmaster Tools emphasizes the role of IP and domain reputation in spam filtering, with IPv6 misconfigurations contributing to poor reputation. Microsoft Docs suggests checking sender reputation, DNS configuration, and adhering to sending policies. The IETF documentation highlights that IPv6 implementation can affect email deliverability based on server configurations.

Key findings

  • Reputation Matters: Gmail uses IP and domain reputation to filter spam, as highlighted by Google Postmaster Tools.
  • IPv6 Impact: IPv6 misconfigurations can lead to poor IP reputation and subsequent email rejection, as noted by both Google and IETF documentation.
  • Standard Protocols: Basic email transmission and formatting standards are defined in RFCs but don't address modern filtering practices.
  • Policies and Configuration: Following Microsoft's sending policies and ensuring proper DNS configuration are crucial for deliverability, according to Microsoft Docs.

Key considerations

  • Monitor Reputation: Regularly monitor IP and domain reputation using tools like Google Postmaster Tools.
  • Configure IPv6 Correctly: Ensure proper configuration of IPv6 settings to avoid deliverability issues.
  • Adhere to Policies: Comply with both Gmail's and Microsoft's sending policies to avoid being flagged as spam.
  • Review DNS Settings: Verify and correct DNS settings to ensure proper email routing and authentication.
Technical article

Documentation from RFC Editor details the original SMTP (Simple Mail Transfer Protocol) standards, which govern how email is transmitted across the internet. It outlines basic requirements for message formatting and delivery, though it doesn't specifically address IPv6 or Gmail's filtering practices.

December 2024 - RFC Editor
Technical article

Documentation from Microsoft Docs outlines troubleshooting steps for email delivery issues from Microsoft accounts. It suggests checking sender reputation, ensuring proper DNS configuration, and following Microsoft's sending policies to avoid being flagged as spam by Gmail.

November 2023 - Microsoft Docs
Technical article

Documentation from Google Postmaster Tools shares that Gmail uses IP reputation and domain reputation to filter spam. Poor IP reputation, potentially due to IPv6 misconfigurations or shared IPs with spammers, can lead to rejection. They recommend monitoring sender reputation and following best practices.

December 2023 - Google Postmaster Tools
Technical article

Documentation from RFC Editor describes the current standard for Internet Message Format. It covers aspects like header fields and message structure, important for ensuring that emails are correctly interpreted by receiving servers like Gmail. This does not delve into IPv6 issues.

February 2024 - RFC Editor
Technical article

Documentation from IETF outlines the specifications for IPv6 and its implementation within the Internet Protocol Suite. It is mentioned how IPv6 can affect email deliverability depending on server configurations.

February 2023 - IETF