Summary
Proofpoint, as an intermediary email security solution, can significantly affect email authentication for organizational Outlook domains. It alters the email path, potentially leading to SPF, DKIM, and DMARC validation failures because the receiving server sees Proofpoint's IP address instead of the original sender's. To mitigate these issues, organizations should configure Exchange Online Connectors to recognize Proofpoint's IPs as trusted sources, implement ARC (Authenticated Received Chain) to preserve authentication results across multiple hops, and enable Enhanced Filtering for Connectors. Regular monitoring of email logs and careful analysis of email headers are also essential. Additionally, proper management of bypass lists, correct configuration of internal domains, and the use of TLS encryption contribute to a more secure and reliable email system. Verifying DMARC settings is also a crucial step to maintain email authentication integrity.
Key findings
- SPF/DKIM Failures: Proofpoint can cause SPF and DKIM failures as its IP address may not match the sender's records.
- Header Alteration: Proofpoint's filtering can flag legitimate emails or alter headers, triggering spam filters.
- IP Address Discrepancy: EOP sees Proofpoint's IP instead of the original sender's, affecting authentication checks.
- Authentication Result Stripping: Proofpoint might strip or alter headers essential for SPF, DKIM, and DMARC validation.
- ARC Importance: ARC is critical for preserving authentication results across multiple email hops.
Key considerations
- Connector Configuration: Properly configure Exchange Online Connectors for Proofpoint.
- SPF Record Updates: Ensure SPF records include Proofpoint's IPs or use ARC.
- Header Analysis: Analyze email headers to understand Proofpoint's impact.
- Log Monitoring: Regularly monitor email logs for authentication failures and misconfigurations.
- Bypass List Management: Carefully manage bypass lists to prevent security vulnerabilities.
- Internal Domain Setup: Configure internal domains correctly for proper authentication.
- TLS Encryption: Use TLS encryption to secure email communications.
- DMARC Verification: Regularly verify DMARC settings
What email marketers say
10 marketer opinions
Proofpoint, as a third-party email security solution, impacts email authentication for organizational Outlook domains by altering email paths and potentially causing SPF, DKIM, and DMARC validation failures. This is because Proofpoint's IP addresses may not match the sender's SPF records. Mitigation strategies include configuring Exchange Online Connectors to recognize Proofpoint's IPs, implementing ARC to preserve authentication results, carefully analyzing email headers, monitoring email logs, managing bypass lists judiciously, configuring internal domains correctly, and using TLS encryption. Proper configuration and monitoring are crucial to maintaining email deliverability and security.
Key opinions
- SPF Failures: Proofpoint can cause SPF failures because its IP addresses may not match the sender's SPF records.
- Header Alteration: Proofpoint's filtering might flag legitimate emails or alter headers, triggering spam filters.
- Authentication Results: It's crucial to ensure Proofpoint is configured to properly forward authentication results to Exchange Online.
- Inbound Connectors: Configuring Exchange Online Connectors to recognize Proofpoint's IPs as trusted sources is essential.
- Email Log Insights: Email logs provide insights into authentication failures, spam filtering, and potential misconfigurations.
Key considerations
- SPF Records: Organizations should ensure their SPF records include Proofpoint's IPs or use mechanisms like ARC.
- ARC Implementation: Implementing ARC helps preserve authentication results across multiple hops.
- Header Analysis: Carefully analyze email headers to understand the email's path and modifications made by Proofpoint.
- Log Monitoring: Regularly monitor email logs to identify and address authentication issues proactively.
- Bypass List Management: Manage bypass lists carefully to avoid introducing security vulnerabilities.
- Internal Domain Configuration: Correctly configure internal domains to ensure internal emails are properly authenticated.
- TLS Encryption: Use TLS encryption to secure email communications and protect data integrity.
Marketer view
Email marketer from Security Forums emphasizes the importance of regularly monitoring email logs when using Proofpoint. They explain that logs can provide valuable insights into email authentication failures, spam filtering issues, and potential misconfigurations. Proactive monitoring allows organizations to quickly identify and address any problems that may arise.
19 Mar 2024 - Security Forums
Marketer view
Email marketer from Super User suggests carefully analyzing email headers when using Proofpoint. They recommend examining the `Received:` headers to understand the email's path and identify any modifications made by Proofpoint. This analysis can help pinpoint issues with SPF, DKIM, or DMARC validation and ensure proper configuration.
25 Dec 2023 - Super User
What the experts say
1 expert opinions
ProofPoint's filtering process can disrupt SPF and DKIM records, as the IP address making the final delivery might not align with the sender's SPF record. It is crucial to verify DMARC settings to maintain email authentication integrity.
Key opinions
- SPF/DKIM Impact: ProofPoint filtering can affect SPF and DKIM records.
- IP Mismatch: The final delivery IP may not match the sender's SPF record.
Key considerations
- DMARC Verification: Check DMARC settings to ensure email authentication.
Expert view
Expert from Word to the Wise explains that when ProofPoint filters email it can affect SPF and DKIM records. A receiving server checks the SPF record of the sending domain, and if the email is routed through Proofpoint, the IP address making the final delivery might not match the IPs listed in the sender's SPF record. She suggests that it is best practice to also check DMARC settings if this happens.
28 Nov 2024 - Word to the Wise
What the documentation says
6 technical articles
Proofpoint, acting as an intermediary for inbound email, can impact email authentication in organizational Outlook domains. EOP sees Proofpoint's IP instead of the original sender's, potentially affecting spam filtering. Proper configuration of connectors, especially Enhanced Filtering, helps Exchange Online identify the original sender. ARC (Authenticated Received Chain) preserves authentication results through multiple hops, mitigating authentication failures. Configuring inbound connectors to recognize Proofpoint's IPs is crucial to avoid SPF/DKIM failures.
Key findings
- EOP IP Address: EOP may see Proofpoint's IP instead of the original sender's, affecting spam filtering.
- Authentication Impact: Proofpoint's intermediary role can impact SPF, DKIM, and DMARC validation.
- ARC Preservation: ARC preserves authentication results when email is processed by intermediaries like Proofpoint.
Key considerations
- Connector Configuration: Configure connectors correctly to ensure accurate sender identification.
- Enhanced Filtering: Implement Enhanced Filtering for Connectors in Exchange Online.
- ARC Implementation: Implement ARC to mitigate authentication failures caused by third-party security solutions.
- Inbound Connectors: Configure inbound connectors to recognize Proofpoint's IPs as trusted.
Technical article
Documentation from Proofpoint Support explains configuring inbound connectors to ensure mail flow and authentication is handled correctly. It mentions the importance of setting up connectors that recognize Proofpoint's IPs as trusted to avoid SPF or DKIM failures on legitimate emails.
28 Jul 2022 - Proofpoint Support
Technical article
Documentation from RFC Editor details the technical specifications of ARC (Authenticated Received Chain). It explains how ARC works to preserve email authentication results by creating a chain of signatures that validate the authenticity of each hop in the email's journey. This ensures that receiving servers can trust the email's authentication status, even after it has been processed by intermediaries like Proofpoint.
17 May 2023 - RFC Editor
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