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How to troubleshoot B2B email quarantine issues with new dedicated IPs and strict security settings?
Summary
Troubleshooting B2B email quarantine issues with new dedicated IPs and strict security settings requires a multi-pronged approach. It starts with verifying proper email authentication (SPF, DKIM, DMARC) and ensuring these records are correctly set up and validated, preferably tested against a domain different from your own. Building a positive IP reputation is crucial, beginning with a gradual IP warm-up process by sending small volumes of emails to highly engaged subscribers and avoiding engagement traps. Consideration must also be given to the recipient side, including adherence to bulk sender guidelines, security policies from providers like Microsoft's EOP and Cisco's ESA, and potential filtering by services like Mimecast, requiring whitelisting by the recipient’s IT department. Communicating platform changes to customers and providing clear instructions on how to whitelist the new IP or domain is important. Security awareness training for employees to prevent inadvertent whitelisting of malicious senders is essential, as is continuous monitoring of deliverability metrics and sender reputation using tools like Google Postmaster Tools. Utilizing email warming tools, exploring certifications like Return Path, and understanding DMARC specifications further contribute to improving B2B email deliverability.

Key findings

  • Email Authentication: Proper setup and validation of SPF, DKIM, and DMARC records are fundamental for email deliverability.
  • IP Warming and Reputation: Gradual IP warming and monitoring sender reputation are critical for new dedicated IPs.
  • Recipient-Side Factors: Recipient-side email security policies, including whitelisting requirements, significantly impact deliverability.
  • Communication with Customers: Informing customers about platform changes and providing whitelisting instructions reduces quarantine issues.
  • Security Awareness Training: Training employees on email security best practices prevents inadvertent whitelisting of malicious senders.
  • Monitoring and Tools: Continuous monitoring of deliverability metrics and use of email warming tools can help identify and resolve deliverability problems.

Key considerations

  • Domain Verification: Verify authentication with a domain that isn’t your own to eliminate local settings issues.
  • DMARC Policy Implementation: Start with a DMARC policy of 'p=none' and gradually transition to stricter policies like 'p=quarantine' or 'p=reject'.
  • Bulk Sender Guidelines: Adhere to bulk sender guidelines of major email providers like Gmail.
  • Whitelisting: Provide clear and concise instructions on how customers can whitelist your sending IP or domain.
  • Mimecast and Similar Services: Be prepared to work with recipient IT departments to ensure proper whitelisting within their email security configurations.
  • Engagement Traps: Avoid sending emails to addresses that could be engagement traps or unengaged users, as this can negatively impact IP reputation.
  • Email Filter Provider: If problems persist, reach out to the recipient's email filter provider support, such as Proofpoint, for specific guidance.
What email marketers say
11 marketer opinions
Troubleshooting B2B email quarantine issues with new dedicated IPs and strict security settings involves several key strategies. First, ensure proper email authentication (SPF, DKIM, DMARC) is in place and correctly configured. IP warming is crucial, starting with small email volumes to engaged subscribers and gradually increasing over time, while monitoring sender reputation. Also, consider that recipient-side configurations, such as strict spam rules or specific email provider settings (e.g., Mimecast), may require whitelisting the new IP by the recipient's IT department. Informing customers of platform changes and providing whitelisting instructions can help. Utilizing email warming tools, monitoring deliverability metrics, and exploring certifications like Return Path can further improve deliverability. A comprehensive deliverability checklist covering authentication, IP warming, list hygiene, content optimization, and continuous monitoring is essential.

Key opinions

  • Authentication: Proper email authentication (SPF, DKIM, DMARC) is essential for B2B email delivery and preventing quarantine.
  • IP Warming: Warming up new dedicated IPs gradually and monitoring sender reputation are critical steps.
  • Recipient Configuration: Recipient-side configurations (e.g., Mimecast) may require whitelisting the new IP.
  • Communication: Informing customers about platform changes and providing whitelisting instructions can prevent quarantine.
  • Tools: Email warming tools and deliverability monitoring metrics can help identify and resolve issues.

Key considerations

  • DMARC Policy: Start with a DMARC policy of 'p=none' and gradually move to 'p=quarantine' or 'p=reject' as confidence increases.
  • Whitelist Instructions: Provide clear instructions to customers on how to whitelist the new IP or domain.
  • External Source Issues: Be aware that sending from an authenticated domain from an external source can still cause issues with some providers.
  • Dedicated IPs: Ensure dedicated IPs for internal communication are whitelisted to avoid spam filters.
  • Certification: Explore Return Path Certification to enhance sender reputation.
Marketer view
Email marketer from Stack Overflow responds that some B2B email providers, like Mimecast, have strict configurations that may block emails even if properly authenticated. Contact the recipient's IT department or email administrator to ensure the new IP address is whitelisted within their organization's email security settings.
19 May 2022 - Stack Overflow
Marketer view
Email marketer from Gmass shares that using their platform's warm-up tools and features can help increase the sending reputation. This involves sending small volumes initially to engaged recipients to improve the domain's credibility with major email providers.
5 Apr 2024 - Gmass
What the experts say
4 expert opinions
Troubleshooting B2B email quarantine issues with new dedicated IPs and strict security settings requires a multi-faceted approach. Primarily, verifying the correct setup and authentication of emails using SPF, DKIM, and DMARC is critical, potentially using a business domain different from your own for testing. A new IP's reputation is crucial, avoid engagement traps, use good list hygiene and warm up IP address by sending small volumes initially to engaged recipients to build a positive reputation. While some providers (like Gmail) necessitate IP warmup, others might not be as sensitive. For those, contacting their support (like Proofpoint) can provide tailored insights.

Key opinions

  • Authentication: Verify SPF, DKIM, and DMARC records are correctly configured and authenticated, as incorrect setups are a major cause of quarantine issues.
  • IP Reputation: New dedicated IP addresses require building a positive reputation to avoid being flagged as spam.
  • Warming up: IP warmup helps establish a positive reputation more quickly by sending small volumes of emails to highly engaged users.
  • Filter Provider: Different filter providers may have varying requirements; some necessitate IP warmup, while others need direct communication for troubleshooting.

Key considerations

  • Domain Verification: Verify authentication with a domain that isn’t your own to eliminate local settings issues.
  • Engagement Traps: Avoid sending to engagement traps or unengaged users, as this can quickly damage the IP's reputation.
  • Support Contact: Consider reaching out to the recipient's email filter provider support (e.g., Proofpoint) for specific guidance.
  • Monitoring Tools: Monitor IP reputation using tools like Google Postmaster Tools.
Expert view
Expert from Email Geeks asks if the customer is using DMARC policy and if the messages are correctly authenticated. She also suggests verifying with a business domain that isn’t the sender's, as mailing to own domains adds complexity. She then notes that if the filter provider is Gmail, warmup is necessary, but potentially shorter than a new domain/IP combo.
23 Nov 2024 - Email Geeks
Expert view
Expert from Email Geeks suggests reaching out to Proofpoint customer support to inquire about potential issues, though she doesn't believe warmup is a significant factor with Proofpoint.
5 Dec 2023 - Email Geeks
What the documentation says
5 technical articles
Troubleshooting B2B email quarantine issues with new dedicated IPs and strict security settings requires a strong understanding of how email security systems operate. Microsoft's Exchange Online Protection (EOP), Google's Gmail, Cisco's Email Security Appliance (ESA), and Proofpoint's security solutions all rely on sender reputation, content analysis, and adherence to email authentication standards (SPF, DKIM, DMARC). New IPs must build a positive reputation before sending large volumes of emails. Furthermore, employee security awareness training is vital to prevent users from inadvertently whitelisting malicious senders or falling victim to phishing attacks.

Key findings

  • Authentication Standards: SPF, DKIM, and DMARC records must be properly configured to ensure email authentication.
  • Sender Reputation: New IP addresses must establish a positive sender reputation by adhering to best practices.
  • Bulk Sender Guidelines: Adhering to bulk sender guidelines, especially those of Gmail, is crucial for deliverability.
  • Security Awareness: Employee security awareness training is necessary to prevent inadvertent whitelisting of malicious senders.
  • Understanding RFC: Knowledge of DMARC RFC specifications is important.

Key considerations

  • Message Headers: Inspect message headers to troubleshoot quarantine issues.
  • Anti-Spam Policies: Review anti-spam policies to ensure proper configuration.
  • Unsubscribe Options: Provide easy unsubscribe options to reduce spam complaints.
  • Content Analysis: Understand how systems evaluate content to avoid triggering spam filters.
Technical article
Documentation from Proofpoint emphasizes the importance of security awareness training for employees in B2B environments. Educating users about phishing and social engineering attacks can prevent them from inadvertently whitelisting malicious senders or clicking on dangerous links that bypass security measures.
4 Dec 2024 - Proofpoint
Technical article
Documentation from Google Workspace Admin Help explains that for sending to Gmail addresses, adhere to Google's bulk sender guidelines. This includes maintaining low spam complaint rates, properly authenticating emails, and providing easy unsubscribe options. New IP addresses must build a reputation before sending large volumes.
17 Nov 2024 - Google Workspace Admin Help
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