How to Write Terrible Emails Well?
summary
Describes how large email volumes create a profitable spam market and demonstrates building and testing spam end-to-end using Telnet/OpenSSL/Postfix to submit mail and MailSlurp and MXToolbox to receive and inspect messages. Covers using SPF, DKIM, DMARC checks and SpamAssassin scoring to measure delivery risk, with demos of forging DKIM by pairing a server private key with a published public key, exploiting MailChannels SPF misconfigurations, and evading classifiers via Unicode token substitution and selective base64 encoding.
AI-written summary · about
chapters (12)
- 0:00Introduction
- 1:03Talk goals and plan
- 3:29Telnet and SMTP basics
- 6:15Account hacking and encryption
- 9:50Postfix server setup
- 12:19SPF and DNS checks
- 14:52DKIM authentication
- 18:25Email filtering and reputation
- 22:13Email content analysis
- 26:23Receiving server rules
- 27:46Bypassing filters and tricks
- 28:50Conclusion and legal warnings
related talks
12mEMAIL!
56mEmail vs Capitalism, or, Why We Can't Have Nice Things
44mModern Email Security
42mThe not so simple mail transport protocol
24mEnd-to-End Measurements of Email Spoofing Attacks
20m"Return to Sender: Bypassing Email Spam & Malware Filters"
22mNot that Simple: Email Delivery in the 21st Century
44mSecurely Sending Email in 2024