Read Time: 5 min

Inbox Nightmares: Webinar Recording + Q&A


As if 2020 hasn’t been scary enough, email marketers are facing new trends and a changing marketing landscape that threaten to overwhelm even the best laid plans. Dark Mode, deliverability, changing customer expectations, holidays unlike years past… There’s a lot keeping us up at night.

That’s why we invited Helen and Milton, two of our friends from Oracle, to talk through some of the scariest topics in email marketing.

Didn’t have a chance to watch the webinar live? Don’t worry. You can access the full recording at any time, check out the slides, and read the Q&A below.


A big thank you to everyone who chimed in during the webinar with a question! Here’s a recap of our answers to the most popular questions, along with our take on some of the questions we didn’t get to during the live webinar.

Can we override Dark Mode styles using CSS?

Jason: For some email clients, you can use custom CSS to create a better experience for subscribers viewing in Dark Mode. Our Ultimate Guide to Dark Mode for Email Marketers goes over all of the techniques you need to know. Just be aware that not all email clients support custom CSS for Dark Mode, so it won’t work everywhere.

Does Gmail Annotations make sense for B2B audiences?

Milton: I think it all depends on how many gmail users you have in your audience. If Gmail is greater than 15-20%, I think it’s worth it and makes sense. Also, if you are doing a lot of offers, then that also makes sense to use this feature.

My biggest fear is sending to the wrong list! What are your best practices for those dreaded “oops” emails?

Helen: Be honest, stay true to your brand voice, and get it out ASAP. Oops emails often have great response rates, perhaps because it humanizes the organization.

Jason: I agree with Helen. We actually published a guide called How to Recover From Email Marketing Mistakes with even more advice, including guidance on whether or not you actually need to send an apology email. Worth checking out.

Is it safe to ignore devices and operating systems more than about 5 years old?

Jason: Generally speaking, yes. But it does depend on your audience. Some industries—especially heavily regulated ones like government, finance, and healthcare—tend to have much longer upgrade cycles, so they could very easily be using older devices and operating systems. As always, the best way to determine which email clients and devices you should pay attention to is by looking at your own email analytics to see what your subscribers actually use.

Can you talk about emails going to the junk folder because of low subscriber engagement?

Helen: If an email platform sees very little engagement from recipients, they conclude that people don’t want what you’re sending.

Milton: Each domain has its own algorithm in terms of what is categorized as junk/spam but for the most part, if a domain is seeing low engagement from an IP address, that domain will sometimes ask the user if they’d like to unsubscribe (Gmail for example) and users either are unsubscribing or spamming it. Always monitor your domains by adding a tracking pixel to your emails and target engaged users within the past year.

What do you recommend when you start seeing an increase in hard bounces for a specific domain?

Helen: Are they addresses that you’ve sent to in the past, and they have engaged and now suddenly they are hard bouncing? Check out the domain – is it a small company that maybe doesn’t exist anymore? Reach out to them, if possible – or have a deliverability consultant reach out – maybe they made a change or purged their old data to delete obsolete inboxes. Ultimately, there’s not much to do about a hard bounce, but it might satisfy your curiosity to get those kinds of answers.

Milton: Mark any hard bounces as undeliverable or remove from list. This usually means that the domain may not exist or the user’s email has been removed.

How long should I wait before I stop sending to unresponsive subscribers?

Helen: I agree that 12-13 months is good. For most of the year I’d suggest even tighter – 6-9 months, but with holidays coming up you can open your recency data window to 13 months to catch people who last engaged last holiday season. Remember to treat your recency segments differently – if they haven’t opened in 8 months, don’t send them daily emails like you would someone who opened last week.

Milton: 1 year is the average, but it depends on the business and peak seasons for that business. On the call, we also mentioned using brick and mortar data to incorporate into your engaged audience. If they have purchased but haven’t clicked/opened, they may still be into the brand. You can also look to target them in other channels as some folks prefer SMS/push.