Where does your eMail really go? by Chris Wheeler @ChrisAWheeler

Originally posted at the Email Experience Blog (EEC) here and at the Bronto blog here.

The internet was designed to be a free exchange of information wherein anyone, upon a loose framework mainly having to do with networking and rendering capabilities, could join, share and digest what they wanted. Email was developed as a predecessor to the internet.  Again, one in which, as long as you had the most basic SMTP compliancy between networks, messages would be handed off between point A to B.

Today, email has turned into a monumentally powerful marketing tool and communication channel that still rivals the internet and other upcoming social networks, regardless of which side of the “email is dying” debate you fall under. With email marketing, forward to a friend, sharing links, email filters and forwarders, along with major ISPs providing outsourcing solutions (like Google Apps), the audit trail of an email is sometimes all but impossible to decipher without CSI level forensic header analysis.

But, you don’t care about all this.

What should you care about?

When you place an order to have something delivered with the USPS, UPS or FedEx, that item almost never leaves that company’s chain of custody.  Meaning, if you dropped it off with FedEx, the recipient will most likely receive it with FedEx.  Again, there are exceptions, but the vast majority of the time this is the rule.  When you send an email out, though, it may be going to a Yahoo! domain address, then forwarded on to a Gmail domain address and finally rendered in Outlook 2007.  What can you do to ensure that your mail has the highest rate of making it to its final destination regardless of the cyber hops in the middle?

1. Ask your recipient up front if their email address is still, indeed, the right one to be using. I check over 8 different email accounts on a normal day, and with inbox email aggregators with dynamic collection addresses (such as OtherInbox), I probably have several hundred email addresses (with OtherInBox I can use disposable email addresses) that will get to me somehow.  However, the email address to sign up with your service when I was a fresh college grad and using my Alumni account may no longer be at the top of my list.  So, I appreciate it when companies I do business with ask me if that’s still the one I should have on my account.  If it is, I click through on a prompt when I login.  If not, it takes 2 seconds to change.  I don’t get asked this every time I login, but perhaps, every 6 months or so to ensure the email address is fresh.  Guess what?  My Alumni account is forwarded to my Yahoo! account.  So, I changed it to have my Yahoo! account receive the email directly (and thus avoid any errant filtering on the part of my school).

2. Authenticate outbound email. Period.
DKIM was designed not to break when making multiple hops in an email’s path to the final destination.  Unfortunately SPF will because of the technical nature of email headers, but with DKIM enabled mail, if it comes through at Gmail verified and then is forwarded on to AOL, the DKIM signature stays intact and the message has a higher likelihood of being delivered.

3. Here’s the bad part.  Just like you as a sender pushing mail out to a recipient, when email is forwarded to another domain by the recipient domain, the reputation and deliverability of that mail falls back on the ISP doing the forwarding.  For instance, I run my own domain hosted through Gmail.  When you send an email there, it gets forwarded to Yahoo! which is what I consider my central email nervous system.  But, sometimes, email from Gmail gets bulked at Yahoo! because of Gmail’s reputation.  This means I don’t get my mail.  What can you do about it?  Gently remind your subscribers to check their spam folders for mail that may have accidentally fallen prey to a filter somewhere.  In my case, I’ll get email that randomly gets bulked (as opposed to breaking any obvious best sending practices) and have made it a habit to check my spam folder often.

4. Check your content in multiple web clients. Oftentimes, an email sent to a Comcast domain looks fantastic, but when forwarded to an AOL accounts, looks horrible.  Now, like in #3, a lot of this is out of your control if the actual content is changed en route by the ISP.  But, if you ensure that your content looks good in the different clients, you increase your chances that when an ISP doesn’t reach in and play with the HTML when it’s being forwarded along, it will look fine in the end email inbox.

5. Have unique identifiers or parameters in your unsubscribe links tying an email address back to a particular sender. This way, your email software will understand the “fingerprint” in the unsubscribe link and know for which address an unsubscribe was logged, regardless of which email account the unsubscribe click actually comes from.  For instance, if I unsubscribe from my Yahoo! address on an email that was sent to me originally at a Gmail account but was forwarded on, you could end up shooting yourself in the proverbial foot.  I could have any wanted email to my Yahoo! account stop but the Gmail email continue.  Recipients will oftentimes setup multiple email addresses for one account (such as Amazon.com allowing you to have different customer accounts based on the unique email address and password combination – your significant and you could both use thesmiths@smiths.com but have different passwords to your own accounts), or across multiple accounts you as an ESP or single sender support (wherein I may shop at 3 different stores your ESP hosts email for), so directly tying that recipient’s unsubscribed email address to their preferences (and not the one that happened to actually do the unsubscribing) is key.

This is pretty technical stuff, folks.  But, in order to stay on top of the original intent of email being free flowing and having as few barriers as possible, you must be cognizant of the challenges in your path.  Reach out to your technical team to ensure you’ve got these points covered.  And remember, an email address is easily disposable.  We, as marketers, tend to see them as having high stickiness.  But, recipients can come and go with fluidity and tracking them along the way with their permission (ultimately their keeping you informed of their moves) keeps you in touch with your customers.

Chris Wheeler
Director of Deliverability
Bronto Software

Takeaway: Sending an eMail is like dressing your child up to go out on a cold winter day. Make sure you’ve buttoned it up right so that it arrives in much the same condition it went out as.

Meet the author:

Chris Wheeler

Chris Wheeler

Chris Wheeler is leading the charge to ensure his ESP's customers and staff are well-informed about email marketing practices and technology as well as being the face of deliverability externally. Previously, he created the internal deliverability program at Amazon.com alongside program managing the operations of the email team and was at an ESP leading a team of deliverability consultants. Besides being a frequent contributor on Deliverability.com, Chris is a part of many email industry forums, both business and technical.

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