Marek Loder Customer Success Sending email on behalf of your users 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

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

1. Discuss when sending on behalf of your users may be helpful, or required 2. Explore strategies to send email on behalf of users and the pros and cons of each approach 3. Identify which sending method (or combination of methods) is right for your business What we’re going to cover today?

Why send email on behalf of users?

When it makes sense • Helpdesks • CRMs • Email Service Providers • Web agencies • Other B2B applications

Invisible “sending” This looks right… End Recipient

More obvious “sending” This doesn’t look quite right… End Recipient ?

Why does this matter? • Avoid confusion in email communication • Protect overall brand and reputation • Ensure optimal deliverability

The 3 methods we’ll cover

Whitelist & Blacklist SPF 1

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Domain Keys Identified Mail DKIM

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1 Fully-aligned and Authenticated Customer Domain

Authenticated Customer Domain DKIM SPF DMARC

Looking good! This looks right… End Recipient

What’s required? • DKIM: Your customers will need to add a DKIM TXT record to their DNS. • SPF: Depending on provider, you’ll either need to have your customers add an SPF record, or designate a custom Return- Path. • DMARC SPF alignment requires that the From address domain match the Return-Path domain, so allowing Custom Return-Path is required for full DMARC alignment

Putting the pieces together Add Your Domain Add Custom Return-Path

Putting the pieces together cont.

The Pros • The email recipient (your customers’ customer) will receive email from your customers domain • Recipients never see “via” or “on behalf of” tags for senders • Reputation is tied to your customer’s domain • Enables full DMARC alignment • Maximizes opportunity for reliable delivery

The Downsides • Requires development work to allow customers to add their domain and expose DNS entry values. • Customers need to have access to their DNS and ability/comfort to make changes (many employees rarely touch DNS entries so this may be a challenge) • Requires you to build out a comprehensive communication plan to help your customers understand the authentication process

2 Verified “From” Address

Verified “From” Address DKIM SPF DMARC

Yuck This doesn’t look quite right… End Recipient

Putting the pieces together Add From Email Add From Name Add Reply To Address Verification Confirmation Address Verification Email

The Pros • Quick & Easy • Confirmation email sent to the From address to verify and approve ESP for sending with that address • From address is your customer’s address • No additional setup or DNS records required

The Downsides • Deliverability suffers (without optional authentication) • DKIM signature domain does not match From domain • via or on behalf of note in email clients • SPF/Return-Path domain does not match From domain • Can fail DMARC • What happens if policy for DMARC is set to quarantine or reject?

3 Custom “From” Name

Custom “From” Name DKIM SPF Return-Path DMARC

What’s required • Verify your own domain using a DKIM record • (Optional) Set up a custom return-path for full DMARC alignment and improved deliverability

The Pros • Your customers do not need to verify addresses by email or modify their DNS records • Emails will have great deliverability with DKIM and Return-Path authentication set up • From name can be set to match your customer • Reply-To address can be set to be your customer’s address, so that they can receive replies

The Downsides • Your customer’s domain and addresses are not used • Can cause mistrust with the recipient if they check the actual sending address • Your own domain’s sending reputation can be affected by any bad actors • If there is an issue with your domain reputation, it would affect all of your customers’ sending

Bringing it together: How to choose which method is right for you?

Which option is right for you? • It depends on your priorities and the priorities of your customers • Start simple and expand over time • Clearly communicate advantages/disadvantages to your users for available options • Provide fallback (i.e. authenticate your domain, or default to custom “from name” • Beware of the consequences of taking shortcuts - don’t mask these risks from your customers • If you must take a shortcut, do it responsibly - send from your authenticated domain with a variable “From Name”

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