Your holiday email plan is boring and hurting people: AKA Silent Night, Holy Cow, it’s BFCM

The holiday email discourse gets dusty when you’ve been in the game a while, but If you haven’t already locked down your holiday sending strategy, the clock is ticking. 

Every year, the same chorus pipes up like carolers in perfect harmony: 

 “Warm your IPs early!” “Segment!” “Send more, sell more!”  

All fine advice, but also about as fresh as fruitcake. 

This year, I’m giving “best practices” a heavy side-eye and advocating for strategic heresy: deliverability-safe, emotionally intelligent alternatives to the same tired holiday playbook. 

Less repetition. More randomness. Better results. 

Here are six against-the-grain guidelines to help you sleigh the inbox, even if you’re just starting now. In November. You clearly have a rebellious streak, so don’t stop now: 

When everyone’s shouting in the inbox, your “exclusive” offer becomes a whisper in a war zone. 

The instinct to blast more emails “because it’s Q4” often backfires, especially when mailbox providers and your mutual customers are already overwhelmed by Christmas-adjacent chaos. 

Contrarian Move: Instead of joining the fray, pull back on volume during the noisiest days (Black Friday/Cyber Monday) and ho-ho-home in on your highest-performing segments. 

Sending targeted offers to people most likely to convert beats generic campaigns sprayed like flocking across your entire database. 

Those “Would you like to opt out of holiday emails?” campaigns may seem compassionate, until they hit someone who was barely holding it together that day. 

Even a kind “we know the holidays can be hard” can unintentionally join the long list of things that make them harder. 

Contrarian Move: Bake consent and user controls into your year-round strategy, not just when the sugar cookies hit the fan. Asking subscribers about their preferences during signup or immediately after means you’re thinking proactively, rather than reactively, in the middle of a sentimental inbox crisis. If you can suppress chronically unengaged users without making them take a “does this make you sad?” quiz just to boost your bottom line, you give people space to opt in or out quietly, without touching on trauma. 

Everyone else is queued up for 9 a.m. EST on Black Friday. 

 So what if you just…don’t?  

Contrarian Move: Even mailbox providers have finite resources; sending at an unpopular time can prevent capacity delays, and help your brand stand alone, rather than amongst the crowd of coupons.  

Try off-peak timing like early morning drops, Sunday night sends, or even midnight messages for your insomnia-ridden deal-hunters (we see you, new parents and third-shift warriors). 

Think deep discounts, limited-run merch, or super secret landing pages buried in these offbeat sends. 

It might not drive immediate opens, but once subscribers know your emails occasionally contain hidden gems, they’ll start checking more often. They might even spread the word, building buzz around your list and nudging new signups and conversions along the way. 

Fandom energy, made festive. 

If your infrastructure has been skating by all year, Q4 is when the cracks start to show. 

Gmail, Yahoo, and Microsoft have tightened enforcement on authentication and engagement thresholds, and holiday sending is like shining Rudolph’s nose on all your bad habits. 

• Audit everything ASAP. 

• Look at last year’s results to see what’s worth replicating, and what should be avoided. 

• Check your SPF/DKIM/DMARC alignment. 

• Validate your From: domain and make sure you can receive replies (Microsoft says!) 

• Monitor complaint and delivery trends daily, not just on Cyber Monday. 

If you’re sending via Mailgun’s API, don’t wait until Black Friday to discover your payloads are a mess. 

Here’s your pre-holiday checklist: 

✅ Make sure List-Unsubscribe headers are present and RFC 8058-compliant 

 ✅ Monitor your API error responses — 401s, 403s, 550s (especially from Microsoft) 

 ✅ Revisit segmentation logic if you’re using metadata or tags 

 ✅ Sign with the correct domain and confirm it’s aligned properly 

Because nothing says “happy holidays” like debugging a 403 at 4:03 Christmas morning. 

The rumor mill says mailbox providers crank up the scrutiny during the holidays. 

Let’s be clear: The filters don’t change as much as the sending patterns do. In reality, it’s less “crackdown” and more “capacity issue”. Like a stretchy waistband after five (dozen) holiday cookies, the filtering system is still doing its job, you’re just giving it a whole lot more to work with. 

Contrarian Move: Volume is less important than value! This isn’t a numbers game, you’re in a content competition now. Better senders are a bigger threat than aggressive spam filters.  

Mailbox providers reward strong infrastructure and good behavior, and shoppers reward relevance. Either way, the lazy brands lose. 

(Or: The Best Time to Experiment Was Last Month) 

Trying out a new brand voice? 

Revamping your design? 

Formulating a new emoji-only subject line format? 

Once the holiday noise hits, inboxes are chaotic neutral at best, and experimentation becomes a high-risk gamble with low visibility. 

Test your spooky ideas in September. Lock in what works before Halloween. If you haven’t tested it by now, the best gift you can give your subscribers is restraint. 

Once November hits, stick to proven performers and keep the chaos in the mall, not your deliverability metrics. You’ll give thanks for the stability!  

Tired Advice vs. Fresh Moves 

Holiday success doesn’t come from yelling louder. 

It comes from sending like you mean it — with care, intention, and a dash of rebellion. 

This year, don’t follow the crowd; outsmart it.  

And for the love of all that is holly and jolly…make your messages as appealing to open as the biggest box under the tree. 

Author: Alison Gootee