Tis the season to be prepared

It’s pumpkin spice season! Can you feel the chill in the air? Me, neither -- today’s projected high temperature is 77 degrees (F) here in my adopted hometown of Chicago. Nonetheless, now is when savvy email marketers should be preparing for deliverability success ahead of the upcoming holiday season. The fourth quarter of the year is a big one for email senders, especially retailers. Success involves planning, and planning starts now. (Or a month ago, if you're really ahead of the game.)

Every year I get called upon to provide guidance to senders for that holiday season. You’d think, by now, that perhaps I could just link to a past year’s blog post and be done with it. And sometimes I do -- it hopefully wasn’t bad advice then and it’s not suddenly bad advice now. But keep in mind that deliverability is an evolving landscape, and the problems faced do shift a bit from year to year. Thus, I think it’s good to have this discussion annually.

So without further ado, here are my top five tips for Holiday Deliverability Readiness in 2021:

Review all of your email technical settings. Test and make sure everything’s working properly. Feedback loops are in place and properly receiving and processing complaints. All email messages are signed with DKIM. You’ve finally implemented DMARC to block the bad guys out and confirmed that everything "aligns" to ensure that you won't cause your own DMARC failures. Review your configuration with your email platform manager or deliverability team and make sure every possible technical bit is pointed in the right direction. This is the easy stuff. Look for missed settings or misconfigurations and fix them now, before the big send days ahead.
Make sure you have enough IP addresses if you’re sending large volumes of email messages. Ask ten different people and you’ll get ten different answers, but MY opinion on the matter is that you probably shouldn’t send any more than about two million email messages per day from a single IP address. Yes, you CAN send more than that-- it’ll probably work just fine. It’ll be a lot slower than you want, though. It’s going to take more than an hour to send eight million email messages.
Don’t add new IP addresses into the mix late, if you can help it. If it’s November 15th and you just realized that you need more IP addresses to handle your send volume for Cyber Monday, it’s too late. You really should have been warming those IP addresses a month or two ahead of that date. Holiday email season is a bad time to warm new IP addresses, because almost all marketers have cranked up those marketing efforts, the ISPs are dealing with very high volumes of mail, and they’re possibly struggling to keep up with it all. Spam filters are on a hair trigger. It’s not the best time to wind up the new thing and see what happens.
Don’t dig too deep into your database. So many folks send more mail during this time -- but the smart ones do so very strategically. Emailing more often or emailing new content is one thing, but digging out lists of people you haven’t touched in ten years is going to cause a deliverability disaster. Sending unwanted mail is going to get you blocked -- and that blocking is going to hurt you more than ever, because of the timing and season. Don't test the limits to see what you can get away with. You'll regret it.
It’s in your best interest to not have to ask for favors. The folks at Yahoo, Comcast, Microsoft, and all of those ISPs that have postmaster pages and unblock forms, the number of requests for help they get during this period is elevated. Nobody’s paying to provide them additional staff to deal with those extra requests, either. So it’s going to take longer for them to get back to people, and it’s possible that some requests for help could even fall through the cracks. And keep in mind that these teams are not staffed around the clock, and are likely going to be closed on various holidays. The more you can handle yourself -- the more issues you can prevent ahead of time, without having to wait for assistance from an ISP, the better off you are going to be.
Bonus tip! Especially be cautious when it comes to sending to Microsoft subscribers. Microsoft is the quickest to block, and the most likely to deny your request for unblocking. (In particular, minimize volume spikes -- they often seem to think that unexpected spikes in volume must mean that a sending IP address is suddenly spewing botnet spam.) For more help with Microsoft deliverability, check out my recent “Why does Microsoft hate you?” post, the Microsoft OLC Deliverability Guide, and the list of Microsoft OLC domains, useful if you want to segment by ISP to help improve deliverability success. Don't be afraid to reach out to your friendly neighborhood deliverability consultant to talk Microsoft strategy in more detail. It can be a tough challenge; better not to go it alone.

As always, I hope all of this guidance helps and that you have a holiday season free of deliverability challenges. Good luck!