📧 Postfix/ISPConfig “Critical Mail” Troubleshooting & Hardening Guide (2025 Edition)

Table of Contents

1. Introduction
2. How Mail Filtering Really Works in ISPConfig
3. Symptoms and Real-World Examples
4. Quick Fix: ISPConfig Server Whitelist
5. Root Causes & Why Whitelisting Sometimes Fails
6. Step-by-Step Troubleshooting Decision Tree
7. Best Practices for 2FA/OTP Delivery Reliability
8. Example: ISPConfig Whitelisting That Actually Works
9. Testing and Verification
10. Advanced: When and How to Tune Filters or Disable Temporarily
11. Appendix: Deeper Dives, Tools, and References

1. Introduction

This guide’s goal: Keep critical transactional, 2FA, and OTP emails from providers (OpenAI, Google, banks, Mandrill, etc.) reliably landing in your inbox—every time, no exceptions—on an ISPConfig-managed Postfix server.

2. How Mail Filtering Really Works in ISPConfig

• Postfix handles SMTP but delegates anti-spam, greylisting, virus scanning, and filtering to background services (Amavis, Rspamd, SpamAssassin, ClamAV, etc.).
• ISPConfig manages user/mail domain policies, but filter decisions are often made outside of Postfix’s own config, in anti-spam engines, not by Postfix itself.
• Whitelisting in Postfix config (main.cf, header/body checks) is not enough if you’re running Amavis, SpamAssassin, or Rspamd via ISPConfig—they may still block mail unless you whitelist via the control panel or directly in the spam filter config.

3. Symptoms and Real-World Examples

• 2FA/OTP/password reset emails missing or delayed
• Email log shows milter-reject: END-OF-MESSAGE ... 4.7.1 Try again later
• Sender uses a third-party (like Mandrill, SendGrid), not their own domain!
• Whitelisting via Postfix or SpamAssassin has no effect, but adding the domain in ISPConfig “Server Whitelist” works instantly

4. Quick Fix: ISPConfig Server Whitelist

If you do only one thing: Go to ISPConfig > Email > Server Whitelist, add the sending domain used in the actual email’s Return-Path/Envelope-From, e.g.,

• mandrillapp.com (for emails from OpenAI, many SaaS apps)
• sendgrid.net
• tm.openai.com (sometimes, but may not be enough—see below)

Why this works: Server-level whitelisting in ISPConfig tells all mail filters to always allow mail from those senders for all domains on your server. This bypasses most filter-level rejections, even if SpamAssassin or Amavis is running.

5. Root Causes & Why Whitelisting Sometimes Fails

Common reasons 2FA/OTP emails are lost or delayed:

• The sender’s domain is not what you expect. (e.g. OpenAI uses mandrillapp.com for transactional mail, not just tm.openai.com)
• Postfix’s built-in whitelisting doesn’t override anti-spam milters or greylisting.
• Filtering happens in Amavis/Rspamd/SpamAssassin, which have their own whitelists. ISPConfig’s “Server Whitelist” controls these filters directly.
• Greylisting can cause one-time delays, but shouldn’t drop mail.
• The “From:” header and the actual sending (Return-Path/Envelope-From) domain can differ. Whitelist the actual sender domain in the mail headers—use the envelope sender in logs!

6. Step-by-Step Troubleshooting Decision Tree

A. Is it just one sender (e.g., OpenAI)?

• Check the mail log for the “from” address and real sender domain:

  grep -i openai /var/log/mail.log | tail -30
  

  Look for lines like: from=<bounces+20216706...@em7877.tm.openai.com>

  • But check further up for lines like: from=<bounce-md_31165340...@mandrillapp.com>

• Whitelist that exact domain in ISPConfig’s Server Whitelist.

B. Are all 2FA/transactional mails affected?

• Repeat the above for each service.
• Don’t trust the “visible” sender—find the real Return-Path/Envelope-From domain in the logs or in the raw message source.

C. Did adding to ISPConfig Server Whitelist fix it?

• Yes: Done!

• No:

  • Check if your filter (Amavis, Rspamd, SpamAssassin) has its own whitelists and add the domain there.
  • Check greylisting settings and add domain as exception if delays persist.

D. If whitelisting doesn’t fix it:

• Is your milter/anti-spam service running? (systemctl status amavis rspamd spamassassin)
• Are you low on RAM/CPU? (free -h)
• Is DNS slow? (dig openai.com)
• Check /etc/postfix/main.cf for unused milters or disabled filters.

E. For Greylisting Delays

• Add domain to greylist whitelist in ISPConfig or /etc/postgrey/whitelist_clients.

7. Best Practices for 2FA/OTP Delivery Reliability

• Whitelist the Envelope-From domain via ISPConfig’s Server Whitelist

  • Not just the visible “From:” address!
• Add all third-party senders used by your services (mandrillapp.com, sendgrid.net, amazonses.com, etc.)
• Whitelist in Amavis/SpamAssassin/Rspamd if you run advanced filter setups
• Keep mail filters up and running at all times (set up Monit, email alerts, etc.)
• Check the mail log for each new service you use—verify the actual sender domain.
• Test with real transactional emails, not just test mails.

8. Example: ISPConfig Whitelisting That Actually Works

A. Where to add (ISPConfig 3.x):

1. Login to ISPConfig Panel
2. Go to Email > Server Whitelist

3. Add a new entry:

   • Domain: mandrillapp.com
   • (Repeat for any other third-party domains as found in logs)
4. Save and apply changes

What this does: Mail from these domains will always be accepted, regardless of filter/greylisting.

B. Finding the Correct Domain to Whitelist

Check the “Return-Path” or log lines:

• Example log entry:

  from=<bounce-md_31165340.683fcd82...@mandrillapp.com>
  

• Whitelist: mandrillapp.com

9. Testing and Verification

1. Send a real OTP/2FA/test email from the service
2. Check your inbox

3. If missing or delayed, check /var/log/mail.log and look for:

   • Temporary rejections (4xx errors)
   • Repeated attempts before success (greylisting symptom)
   • “milter-reject” or “spam” related soft bounces
4. If mail arrives immediately after whitelisting—success!
5. If not: Re-check the actual sender domain and whitelist that.

10. Advanced: When and How to Tune Filters or Disable Temporarily

• If you need to diagnose whether a milter is the culprit, comment out smtpd_milters and non_smtpd_milters in main.cf and restart postfix.
• If this makes OTPs work, your filter is misconfigured or over-aggressive.
• You can also add “trusted” entries directly to Amavis or Rspamd/SpamAssassin configs—but in most ISPConfig setups, server whitelist is the effective solution.

11. Appendix: Deeper Dives, Tools, and References

• ISPConfig Docs: Server Whitelist
• Postfix Milter
• Rspamd Whitelisting
• Mail log analysis

• Testing with Swaks:

  swaks --to your@email --from test@trusted.com --server your.mail.server
  

• MXToolbox Blacklist Check

Summary Checklist: For Every New Service

• Check the real sender domain in /var/log/mail.log
• Add that domain to ISPConfig Server Whitelist
• Test with a real email
• If still blocked/delayed, check filters and greylisting for that domain
• Monitor mail logs to verify delivery