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DELIVERA
DIAGNOSING DEDICATED IP
01.05.2019
TEEHEE
AKA: What you’re missing out on as an ESP Mailer
THAT OTHER SIDE OF THE STORY
WHY ISPS MANAGE DELIVERABILITY
▸Email Service Engages User for Other Revenue Activities
▸ Users Return If You Host Their Inbox
▸ Gather Data
▸ Context for Targeted Ads
▸Preventing Fraud, Scams, and Phishing
▸Experience!
▸ Postmasters and past experience
▸ Users
MOSTLY COCKTAIL FLAG SEMAPHORE. . .
HOW ISP’S COMMUNICATE
▸ Feedback Loops (sometimes)
▸ SMTP! (Simple Mail Transfer Protocol)
“It’s a lot like Grief. . . it comes in stages. . .”
ROAD TO THE INBOX
DIAGNOSING DELIVERABILITY - SAYING
EHLO
▸Connection Request from HOST
▸ We’re actually not a Mail Server! Bye!
▸ Ok ok, we’re a mail server. Are we open for
business [Server Capacity?]
▸ Do we know this Email HOST? [Recent Activity?]
▸ Do we know this Domain?
▸ Do we know this IP? IP’s Neighbors?
▸ Grey or Black List?
▸EHLO - Hi!
▸ Valid Host Name Format? [Email Server]
▸ Do you TLS? (Everyone should now)
EMAIL HOST
HOST DOMAIN
IP
IP NEIGHBORS
SERVER CAPACITY
HOST NAME FORMAT
CONNECTION
SECURITY
ISP Considers
ROAD TO THE INBOX
DIAGNOSING DELIVERABILITY - PAPERS
PLEASE
▸MAIL FROM - This is the Sender!
▸ FROM Domain & Sub Domain Reputation
▸ Reverse Domain Look-Up (RDNS)
▸ FROM address reputation?
▸ Return Path check? (Where do bounces go)
▸ Different vs. FROM? (sign of bulk mailing)
▸ SPF Certified?
▸RCPT TO *
▸ Real Recipient?
▸ Filtering rules? (e.g. admin, trap)
▸ Recipient vs. Sender (user blocked?)
FROM (SUB) DOMAIN
RDNS
FROM ADDRESS
RETURN PATH
SPF
TO ADDRESS VALID?
TO IS A SPAM TRAP?
TO VS. FROM
REPUTATION
ISP FILTERS
ISP Considers
ROAD TO THE INBOX
DIAGNOSING DELIVERABILITY -
ALRIGHT, WHAT’CHOO GOT?
▸DATA!
▸ Content (including Subject) Reputation
▸ Spammy Content Filter
▸ Content Ratios
▸ Virus & Phishing Checks
▸ DKIM / DMARC Valid
▸ URL’s in the Body (links, images, etc)
▸ IP’s attached to URL's
▸ Scored Filters (e.g. Spam Assassin)
▸250 OK - Game ON!
▸ User’s Turn to Judge
CONTENT
FINGERPRINTS
DKIM
DMARC
URL’S IN BODY
SCORED FILTERS
USERS (MEH)
LIKE FINDING A BRUNCH SPOT IN LA
VIGILANCE & TIMING MATTERS
▸Monitor the &%$#!@ SMTP Logs & Metrics together
▸Catch every instance of bad responses AND the context
▸Ignoring a later content event pollutes the reputation of
everything up to the Mail Server
WHAT DO THEY WANT FROM ME?!
WHAT IS GOOD EMAIL TO AN ISP?
▸User to user, personal email (Communication, sharing)
▸Transactional Emails (PW Recovery, Reservations, Receipts)
▸Content Email (Newsletters, Listings, Informational)
▸* Political Emails (Exempted from CAN SPAM)
▸Brand / Partner (e.g. Google & McAfee)
▸ISP’s Parent / Sister Company / Sub Division
“Sustainable email strategies share qualities
with unblockable email”
DIVE! DIVE! DIVE!
IN CASE OF EMERGENCY. . .
▸ Change Send Rate (including Pausing)
▸ Change a Reputation Source (in this order)
▸ Template / Content / Offer
▸ Domain Reputation (friendly from, from, subdomain)
▸ User Selection / Audience Segments
▸ IP Address (including finding a new IP Block)
▸ Change Reputation Driving Metrics
▸ Engaging Content
▸ Request User Actions - “Expect our mails, Pull from Spam Box, Add to Address Book!”
▸ Have a Conversation
▸ Shared Reputation - RETREAT To the ESP’s!
BYE!
QUESTION? COMMENTS?
BEWILDERED WILDEBEEST
NOISES?

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Scott Shou on e-mail deliverability at the MailCon 2019

  • 2. TEEHEE AKA: What you’re missing out on as an ESP Mailer
  • 3. THAT OTHER SIDE OF THE STORY WHY ISPS MANAGE DELIVERABILITY ▸Email Service Engages User for Other Revenue Activities ▸ Users Return If You Host Their Inbox ▸ Gather Data ▸ Context for Targeted Ads ▸Preventing Fraud, Scams, and Phishing ▸Experience! ▸ Postmasters and past experience ▸ Users
  • 4. MOSTLY COCKTAIL FLAG SEMAPHORE. . . HOW ISP’S COMMUNICATE ▸ Feedback Loops (sometimes) ▸ SMTP! (Simple Mail Transfer Protocol) “It’s a lot like Grief. . . it comes in stages. . .”
  • 5. ROAD TO THE INBOX DIAGNOSING DELIVERABILITY - SAYING EHLO ▸Connection Request from HOST ▸ We’re actually not a Mail Server! Bye! ▸ Ok ok, we’re a mail server. Are we open for business [Server Capacity?] ▸ Do we know this Email HOST? [Recent Activity?] ▸ Do we know this Domain? ▸ Do we know this IP? IP’s Neighbors? ▸ Grey or Black List? ▸EHLO - Hi! ▸ Valid Host Name Format? [Email Server] ▸ Do you TLS? (Everyone should now) EMAIL HOST HOST DOMAIN IP IP NEIGHBORS SERVER CAPACITY HOST NAME FORMAT CONNECTION SECURITY ISP Considers
  • 6. ROAD TO THE INBOX DIAGNOSING DELIVERABILITY - PAPERS PLEASE ▸MAIL FROM - This is the Sender! ▸ FROM Domain & Sub Domain Reputation ▸ Reverse Domain Look-Up (RDNS) ▸ FROM address reputation? ▸ Return Path check? (Where do bounces go) ▸ Different vs. FROM? (sign of bulk mailing) ▸ SPF Certified? ▸RCPT TO * ▸ Real Recipient? ▸ Filtering rules? (e.g. admin, trap) ▸ Recipient vs. Sender (user blocked?) FROM (SUB) DOMAIN RDNS FROM ADDRESS RETURN PATH SPF TO ADDRESS VALID? TO IS A SPAM TRAP? TO VS. FROM REPUTATION ISP FILTERS ISP Considers
  • 7. ROAD TO THE INBOX DIAGNOSING DELIVERABILITY - ALRIGHT, WHAT’CHOO GOT? ▸DATA! ▸ Content (including Subject) Reputation ▸ Spammy Content Filter ▸ Content Ratios ▸ Virus & Phishing Checks ▸ DKIM / DMARC Valid ▸ URL’s in the Body (links, images, etc) ▸ IP’s attached to URL's ▸ Scored Filters (e.g. Spam Assassin) ▸250 OK - Game ON! ▸ User’s Turn to Judge CONTENT FINGERPRINTS DKIM DMARC URL’S IN BODY SCORED FILTERS USERS (MEH)
  • 8. LIKE FINDING A BRUNCH SPOT IN LA VIGILANCE & TIMING MATTERS ▸Monitor the &%$#!@ SMTP Logs & Metrics together ▸Catch every instance of bad responses AND the context ▸Ignoring a later content event pollutes the reputation of everything up to the Mail Server
  • 9. WHAT DO THEY WANT FROM ME?! WHAT IS GOOD EMAIL TO AN ISP? ▸User to user, personal email (Communication, sharing) ▸Transactional Emails (PW Recovery, Reservations, Receipts) ▸Content Email (Newsletters, Listings, Informational) ▸* Political Emails (Exempted from CAN SPAM) ▸Brand / Partner (e.g. Google & McAfee) ▸ISP’s Parent / Sister Company / Sub Division “Sustainable email strategies share qualities with unblockable email”
  • 10. DIVE! DIVE! DIVE! IN CASE OF EMERGENCY. . . ▸ Change Send Rate (including Pausing) ▸ Change a Reputation Source (in this order) ▸ Template / Content / Offer ▸ Domain Reputation (friendly from, from, subdomain) ▸ User Selection / Audience Segments ▸ IP Address (including finding a new IP Block) ▸ Change Reputation Driving Metrics ▸ Engaging Content ▸ Request User Actions - “Expect our mails, Pull from Spam Box, Add to Address Book!” ▸ Have a Conversation ▸ Shared Reputation - RETREAT To the ESP’s!