Summary
Troubleshooting email delivery issues in Microsoft 365 requires a comprehensive approach, starting with basic checks like recipient junk folders and Exchange quarantine logs. Analyzing NDRs, utilizing the Remote Connectivity Analyzer, and performing message traces are vital for identifying specific problems. Ensuring proper domain authentication through SPF, DKIM, and DMARC records is crucial, as is maintaining a good sender reputation by monitoring IP blacklists and spam complaint rates. Additionally, reviewing and adjusting Exchange Online Protection (EOP) settings and warming up new IP addresses after migration can significantly improve deliverability.
Key findings
- Initial Checks & Logging: Review recipient junk folders, Exchange inbound message audit logs, and quarantine.
- NDR Analysis: Examine NDRs for enhanced status codes and diagnostic information.
- Connectivity Tools: Use Remote Connectivity Analyzer and message trace for identifying issues.
- Domain Authentication: Correctly configure SPF, DKIM, and DMARC records.
- Sender Reputation: Monitor IP blacklists and spam complaint rates to maintain a good sender reputation.
- EOP Configuration: Review and adjust Exchange Online Protection (EOP) settings.
- Migration Considerations: Warm up new IP addresses gradually after migration.
Key considerations
- Comprehensive Approach: Employ a multi-faceted approach combining different troubleshooting techniques.
- Regular Monitoring: Continuously monitor sender reputation, authentication, and system health.
- Proactive Testing: Use diagnostic tools proactively to identify potential issues early.
- Authentication Accuracy: Ensure accurate and up-to-date DNS records for email authentication.
- Policy Balance: Balance security and deliverability when configuring EOP settings.
- Post-Migration Strategy: Implement a warming strategy after migrating to a new IP address or infrastructure.
What email marketers say
7 marketer opinions
Troubleshooting email delivery issues in Microsoft 365 involves a multi-faceted approach. Initial steps include checking recipient junk folders, Exchange inbound message audit logs, and defender quarantine logs. Assessing sender reputation and ensuring your IP address isn't blacklisted is crucial. Domain authentication using SPF, DKIM, and DMARC records is essential for verifying email authenticity. Review Exchange Online Protection (EOP) settings to avoid overly restrictive policies, and consider implementing feedback loops to monitor spam complaints from ISPs.
Key opinions
- Initial Checks: Check recipient's junk email folder and Exchange quarantine logs.
- Sender Reputation: Monitor sender reputation and ensure your IP address isn't blacklisted.
- Domain Authentication: Implement SPF, DKIM, and DMARC records for domain authentication.
- EOP Settings: Review Exchange Online Protection (EOP) settings.
- Feedback Loops: Implement feedback loops to monitor spam complaints.
Key considerations
- Comprehensive Approach: Troubleshooting requires a comprehensive approach, addressing various factors.
- Reputation Monitoring: Continuous monitoring of sender reputation is vital for maintaining deliverability.
- Authentication Importance: Proper domain authentication is critical for preventing emails from being marked as spam.
- Policy Configuration: Carefully configure EOP settings to balance security and deliverability.
- Proactive Monitoring: Proactive monitoring through feedback loops can help identify and address issues early.
Marketer view
Email marketer from Reddit explains the first step is to check the recipient's junk email folder. Sometimes, legitimate emails are mistakenly flagged as spam.
23 Oct 2024 - Reddit
Marketer view
Email marketer from Reddit shares to check if your sending IP address is blacklisted on any major blocklists. Being blacklisted can severely impact deliverability. Use online tools to check your IP reputation.
8 Dec 2023 - Reddit
What the experts say
2 expert opinions
Troubleshooting email delivery issues in Microsoft 365 involves addressing factors such as IP address changes after migration, poor IP reputation, incorrect email authentication (SPF, DKIM, DMARC), high spam complaint rates, sending to invalid email addresses, and blacklisting. Gradual IP warming, sender reputation monitoring, and correct authentication are crucial for deliverability.
Key opinions
- Migration Issues: Deliverability problems can arise after migrating to Microsoft 365 due to IP changes.
- Authentication Matters: Incorrect SPF, DKIM, and DMARC records are significant contributors to deliverability failures.
- Reputation is Key: Poor IP reputation is a major cause of email delivery issues.
- Spam Complaints Impact: High spam complaint rates negatively affect deliverability.
- Blacklisting Consequences: Being blacklisted prevents emails from reaching their destination.
Key considerations
- IP Warm-up: Gradually warm up new IP addresses to build a positive sending reputation.
- Regular Monitoring: Continuously monitor sender reputation to detect and address issues early.
- Email Validation: Ensure email addresses are valid and up-to-date to reduce bounce rates and improve reputation.
- Complaint Handling: Address spam complaints promptly to prevent further deliverability issues.
- Authentication Verification: Regularly verify that SPF, DKIM, and DMARC records are correctly configured.
Expert view
Expert from Word to the Wise explains that after migrating to Microsoft 365, deliverability issues can arise from changes in IP addresses and sending infrastructure. It's important to warm up new IP addresses gradually, monitor sender reputation, and ensure proper authentication (SPF, DKIM, DMARC) is in place to establish trust with ISPs.
1 Jul 2022 - Word to the Wise
Expert view
Expert from SpamResource details that several factors can cause delivery issues. These include poor IP reputation, incorrect authentication records (SPF, DKIM, DMARC), high spam complaint rates, sending to invalid email addresses, and being blacklisted by anti-spam organizations. Monitoring these factors is crucial for maintaining good deliverability.
16 Apr 2024 - SpamResource
What the documentation says
4 technical articles
Troubleshooting email delivery issues in Microsoft 365, according to Microsoft Learn documentation, involves analyzing Non-Delivery Reports (NDRs) for enhanced status codes and diagnostic information, utilizing the Remote Connectivity Analyzer to test mail flow and identify DNS, connectivity, or certificate issues, ensuring correct DNS record configuration (SPF, DKIM, DMARC) for authentication, and employing message trace in the Exchange admin center (EAC) to track message paths and pinpoint delays or rejections.
Key findings
- NDR Analysis: NDRs provide key details about email delivery failures.
- Connectivity Analyzer: The Remote Connectivity Analyzer can diagnose mail flow problems.
- DNS Configuration: Proper DNS settings (SPF, DKIM, DMARC) are vital for authentication.
- Message Tracing: Message trace in EAC tracks email paths for troubleshooting.
Key considerations
- NDR Examination: Thoroughly examine NDRs to understand specific delivery issues.
- Proactive Testing: Use the Remote Connectivity Analyzer to proactively test mail flow.
- DNS Verification: Regularly verify DNS records to ensure correct email authentication.
- EAC Familiarity: Become familiar with using message trace in the Exchange admin center.
Technical article
Documentation from Microsoft Learn explains that NDRs, also known as bounce messages, provide information about why an email wasn't delivered. You should Examine the enhanced status code and the diagnostic code in the NDR for specific error information to diagnose the problem.
23 May 2024 - Microsoft Learn
Technical article
Documentation from Microsoft Learn details the importance of properly configuring DNS records (SPF, DKIM, DMARC) to authenticate email and prevent spoofing. It emphasizes that incorrect DNS settings can lead to delivery failures.
17 Dec 2023 - Microsoft Learn
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