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Marek Loder Customer Success Email Authentication What you need to know Patrick Graham Customer Success

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• Spend my days at Postmark onboarding new clients • Work out of our headquarters here in Philadelphia • Big fan of the great outdoors • Newly minted private pilot • Music and coffee aficionado. • I spend my days at Postmark troubleshooting technical problems for our customers • Work remotely from the Pacific Northwest. Marek Loder Patrick Graham

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What is Postmark? A fast & reliable transactional-only email platform for web applications Your customers expect application emails to arrive immediately, not eventually. Reaching the inbox isn’t enough

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1. What are the authentication methods and how do they work? 2. Why are they important for you? What are you going to learn?

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Image source: https://www.flickr.com/photos/eelssej_/413385838 Why do I need email authentication?

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Unauthenticated PayPal phishing email

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1. Protect Reputation 2. Protect Deliverability Email Authentication Methods SPF, DKIM, and DMARC

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Whitelist & Blacklist SPF 1

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‘From Address’: Return-Path: Who the message was sent from Where the message was sent from

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Github’s SPF Record v=spf1 ip4:192.30.252.0/22 include:_spf.google.com include:mail.zendesk.com ~all This is an SPF record Defines an IP range Google and ZenDesk mail servers Accept all mail. (Soft Fail)

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Github’s SPF Record v=spf1 ip4:192.30.252.0/22 include:_spf.google.com include:mail.zendesk.com ~all This is an SPF record Defines an IP range Accept all mail. (Soft Fail) Google and ZenDesk mail servers

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SPF Gotchas…

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Only use one SPF record v=spf1 include:_spf.google.com ~all TXT v=spf1 include:mail.zendesk.com ~all TXT v=spf1 include:_spf.google.com include:mail.zendesk.com ~all TXT SPF Gotchas

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Only 10 lookups SPF Gotchas

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2 Domain Keys Identified Mail DKIM

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1. Private key 2. Public key 3. Signature DKIM Components

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DKIM Private Key -----BEGIN RSA PRIVATE KEY----- MIICXgIBAAKBgQDWnZ5hejTvASYrXmwk/hHOsAFDri2zWYnX2KD+yKB7OG6eVqd6 L0HxcY8ds7HJrEaNtVMoic7XazqHyfhyTagPQ9z1ijdQTAhCwXpO4GOutu5tbTcN bVIgWH/hE8OnDOKuCbLn79VYfIQEu9bnOyKGreU9kuxYROv7737OhnwiEwIDAQAB AoGBAJvwbPtA86NR/2z1r7h1T3UR1+lYbuZpQcovIlPebRT7XQz5w7j5C34m2Clp vt3dqmoe/WxwLXXC+QVfUIGlQV15KmA+2+jjYwVCC0lfLsp+xZxnvOyOcCoppbv7 Lbqt9gmF/JwPOUYq3KD+iVwpKiE89Y5DBOFBmaCk6kA4IyXxAkEA9OK5xX9e9fdf MzdJamQ56oMF5CkspVfCCFI4R5zwkRE4R+1pDgYRpvxe2eHk+gEw7nsMpghh6Von begKCr+2yQJBAOBbMWF3Q+556TuAKnCgWd9ZD4BcBEboMFwwXDCaewFVM6dHHcKS wySKyHBP0QjFoP7ESrHglxC/PWqBQ0TbE/sCQBeKZAlUQTCr4v7tZaVQlTCx/7L7 MkuCsChUnwxjTczkNuDTNbIfazr+L7AKQxS1YJrMQV8El0TzYa7zC2QVIeECQQCN 9aXdQhXdw43sdEBmW1ACntvMIG0kYK6Y5pCuwFCsmzi/06PlBfAsIxSI3DgsEMC5 84I/4xgzJI674WarHuQZAkEAqrceOh0yLADMAJlztXsbh96fk//AtPn20FdW/0dE SFGvG8GqV7B99nj/O1BV6V5mfO3bzCtleAJbaptniIL56A== -----END RSA PRIVATE KEY----- Stored secretly by the sender

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DKIM Public Key google._domainkey.github.com Stored publicly in the sending domain’s DNS

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DKIM Public Key google._domainkey.github.com Selector DKIM specific subdomain Signing domain

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DKIM Public Key google._domainkey.github.com Selector DKIM specific subdomain Signing domain

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DKIM Public Key google._domainkey.github.com Selector DKIM specific subdomain Signing domain

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DKIM Public Key google._domainkey.github.com v=DKIM1\; k=rsa\; p=MIGfMA0GCSqGSIb3DQEBAQUAA4GNADCBiQKBgQCCqkSdyfFtn4S3VkICnzOvsi wAZ60Z79uN4YpwgAzrScaDmn0IfgG9I6AKklaPAzmCIOh1Rl2pB/ O9nMlEhVpvpNyauFXxhGEkqWp4PeMaoAl2j/uy8lhk1EIoEfM42Ifzm6GMymG/ c61rOuorAqQsGAdUif2HyOmJYdXi8x7zfQIDAQAB TXT

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DKIM Signature DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=wildbit.com; s=google; h=from:mime-version:date:message-id:subject:to:cc; bh=i/ep9kKrYpLMJ4OkXiiAVdd16bxlMgi4OcpDEQzV55U=; b=CgpzvIVR3mMRXmktyTXAUBFYM3MNgM77WrpGmSqy2Lyeq6aObuzcBCDgh0ZTkgw8lI A8kVodA4EpFOuc66GrJtLFBoy1MxWzUJP25WgAIPj0plbFObXlpJJKMDC0bEoXSnUZrB DVMEDhw8fyP73mgKKfGGzrfja2nE/kUv1WdfU= SMTP header

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3 Domain-based Message Authentication and Conformance DMARC

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DMARC Special DMARC subdomain _dmarc.gmail.com v=DMARC1\; p=none\; rua=mailto:[email protected] TXT

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DMARC v=DMARC1\; p=none\; rua=mailto:[email protected] _dmarc.gmail.com This is a DMARC record Reporting Policy

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DMARC v=DMARC1\; p=none\; rua=mailto:[email protected] _dmarc.gmail.com This is a DMARC record Reporting Policy

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DMARC Tool A free tool to monitor & implement DMARC dmarc.postmarkapp.com

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Checking Validity Check DKIM, SPF, and DMARC validity in Gmail

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SPF passing and DMARC SPF passing are not the same thing. DMARC SPF alignment requires that the From address domain matches the Return-Path domain DMARC - SPF alignment gotcha

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SPF Domain-based way to say what IPs are allowed to send email for you. DKIM Message-based signatures to verify your email is unmodified. DMARC Domain-based way to tell receivers how to handle authentication failures for your domain. Email Authentication Methods

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A few reasons to consider Postmark…

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Authenticate Sending Domains: DKIM & Return-Path Custom Return-Path DKIM

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Unprecedented Troubleshooting 45 days of email activity Search all your messages Detailed message events Advanced filtering

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Detailed message events, grouped by recipient Full content previews (HTML & Plain Text) Message overview

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Customer support that’s human Made the switch to @postmarkapp today. The customer service and delivery rates are awesome. Samuel Goudie “ Postmark has stellar customer service. I don't think I have ever waited more than a few minutes for a response to an email. Christopher Dundy “ Ashley Dana Marek Patrick

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DMARC Reports MailMason SpamCheck StyleMerge MailBrush Templates Mustachio Webhooks MailHandler postmarkapp.com/labs Check out our free & open source tools at…

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Part of the family. postmarkapp.com Questions? Email [email protected] @postmarkapp