Solving common email pain points: Why email deliverability matters

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    Newsletters are like opinions: Everybody’s got one. Mike Allen. Niche bloggers. Multinational organizations. Probably you.

    Why did the oldest form of mainstream digital content distribution, the email, skyrocket to achieve mass adoption seemingly overnight?

    Because: email popularity has little to do with any technological advancements in the email space (no shade to AMP and anyone embarking on the courageous effort of making email better). Publishers have realized: “our” audience is no longer owned by us.

    In other words, it’s not email that’s changed but our collective realization about the implications of filter bubble algorithms – that the invisible power wielded by Google, Twitter, Facebook, LinkedIn about what content is delivered to which eyeballs when is no longer tenable.

    Email is a popular medium for content today because we’ve realized the inbox is the only space online that allows for reliable content distribution and consumption. The ability to reach someone who has indicated they want to receive our content is not a given anywhere currently – except the email Inbox.

    At the end of the day Facebook owns your Facebook fans, Twitter owns your Twitter followers – and you own your email list.

    Why producing modern email newsletters is so hard

    Launching and sustaining an email newsletter effort can feel like death by a thousand cuts.

    When I oversaw the launch of editorial newsletters in 2015 at the L.A. Times, I never expected I would learn email code. Our requirements seemed basic: We wanted our emails to reliably deliver to readers and to render as we intended on the most popular email clients and devices.

    The production of professional looking email newsletters is time consuming and error prone – to a degree that is almost remarkable in a world of modern technology.

    If you’re involved with email newsletters, at some point you’ll inevitably find yourself feeling frustrated wondering:

    • “Why does the rendering of my newsletter look terrible on Gmail’s mobile inbox app? It looked fine yesterday. Why is it breaking today?
    • “What is up with my open rates? They seem low but I’m not sure how to uncover if there is an issue, and if there is, how do I fix it? Some of my colleagues and friends say they are getting my email newsletter in their spam or promotions folder, but I’m not sure how prevalent this potential deliverability issue is…or what to do about it.
    • “Why does it take so long to physically produce the content, get the formatting right, and make sure all of the links work in my newsletter?
    • “I want to know how different cohorts of audience members are behaving via email and online but finding questions to basic answers feels harder than it should be.... I just want to know who is receiving my email and how they are behaving. Is that so much to ask?”

    Email newsletter production – technology that automates away these pain points – lives in a new space that is currently being defined. A space in-between the content management system “CMS” (e.g. WordPress), email service provider “ESP” (e.g., Mailchimp) and in some cases customer relationship management “CRM” (e.g., Pico, Memberful). Email newsletter production software doesn’t have its own acronym, but as the industry matures, existing companies are offering email newsletter add-ons, and new email newsletter services are sprouting up.

    Email Deliverability Tips

    The first step to owning your audience online is understanding the basics of email deliverability. Email delivery proves to be challenging because the algorithms created to keep the inbox free from bad actors (spammers, spoofers, phishers 🐠) by nature need to remain a bit of a mystery. The fact that bad actors will continue to exist means email deliverability will never be “solved”.

    Various organizations exist (ESPC, MAAWG, etc. ) to collaborate and monitor the email ecosystem so that we’re able to continue to use email without it being overrun by spam.

    With this knowledge you’ll avoid unknowingly using one or multiple techniques used by spammers to circumvent spam filters, and ultimately avoid a lot of frustration and time spent wondering if your emails are being successfully delivered to readers.

    Here are three helpful things to know and check for your newsletter. Email deliverability is affected by the:

    1. IP address from which your email was sent as well as SPF and DKIM protocol.

    Metadata – data stored in the sent email about the sent email – provides information that is used to determine if your email is spam or not.

    IP Address: Email is sent from a location – an IP Address. You can check the IP address of where any email was sent, which will also tell you what email service provider a given sender is using, and if that IP address is on any spam lists. Many email service providers use shared IP Addresses, meaning your sender reputation is based on the reputation of other people who you do not know who share your sent from IP Address. If one of those actors is a spammer, your email deliverability will suffer. To avoid this, you can get a dedicated IP address, which is not expensive. The cost varies by where you purchase the IP Address but is generally less than $50.

    SPF / DKIM: Sender Policy Framework ‘SPF’ and DomainKeys Identified Mail ‘DKIM’ contain information in the metadata of your email that authenticate the emails you send. They are free to setup and prevent spammers from overrunning our inboxes. DKIM and SPF provide a way for proving you are the owner of your online domain – eg. mywebsite.com.

    How to find your metadata: You can check the IP address of where any email was sent, which will also tell you what email service provider a given sender is using, and if that IP address is on any spam lists. You can do this for free by looking at the information of any email you receive in your own inbox.

    1. Open the email you want to check.
    2. Get more information about the email: In Gmail, click on the three dots in the top right corner, then “Download Message.” You’ll see a new browser window open.
    3. This window will contain information about the metadata of your email. You will see the DKIM, SPF, and IP address of that particular email.
    • DKIM will pass with your domain URL, which will be displayed.
    • SPF will pass with an IP address (the IP address of your sent email). If you want to see what email service provider someone is using or if your IP is on any black lists, you can input this IP address into a free service such as “https://whatismyipaddress.com”. You can also pay for a service like ReturnPath to go beyond simple DKIM and SPF verification.

    Takeaway: Make sure you’ve successfully verified your domain (DKIM and SPF) and consider moving away from using a shared IP to purchasing your own dedicated IP. Dedicated IPs are inexpensive. Check address periodically to see if you are on any spam lists, or for any individual email where open rates seem particularly low. If your DKIM or SPF are not passing, make sure you verify your domain ownership – this is done through your email service provider.

    2. Nature of the links (URLS) in your email.

    Avoid sending links with many redirects and shortened urls. The links you send or the links you click on via email often have a number of redirects. The reputation of the domain of that redirect affects the deliverability of your email. The ESP tracking is one re-direct; if you use Google Analytics, that’s another. Ad hosting? That’s another. Re-directs add up fast. Speaking of redirects, including a shortened link in email can be risky for deliverability. Shortened links are a method used by bad actors to mask the nefarious destination of the link URL. If you use a shortened URL in your newsletter, your entire email could end up in the spam filter.

    How check the URL redirects: You can track the journey of the various redirects of a single email link from typing $curl in your terminal or visiting a website such as RedirectCheck.com.

    Takeaway: Do not use bit.ly, tinyurl.com, or other shortened links in your email. If an advertiser asks you to include a shortened URL, kindly tell them you will provide them tracking via another method.

    3. Kilobyte size of the content of your email.

    Email is a HTML file comprised of a number of elements, some seen (images, text) and unseen (namely CSS code that affects how an email is rendered). The size of the HTML file is counted in kilobytes. To avoid deliverability issues, try to keep the size of your email below 100kb. WYSIWYG editors add a lot of weight to the back end of your email code – the HTML styles and structure of your email separate from your editorial content. If your email template relies on WYSIWYG technology (as opposed to a custom developed email template) your newsletter is likely to go over the kilobyte limit of 100kb. A solution is to use a more custom email template that has only the code you actually need on the back-end, producing a template that is much leaner than anything you’d find off the shelf.

    How to check the kilobyte size of any email: Download the HTML of your email. When you look at the document information for what you downloaded (the HTML) you will see an associated file size. That is the size of the HTML of your received email. Interestingly, the size of your received email HTML will be different in different email clients because email clients have not gotten together and agreed how email code should be interpreted. This is why coding emails that render consistently is so challenging. Email clients add a substantial amount of their own code to your sent email. Gmail adds the most (while also cutting off received emails at 100kb).

    Takeaway: keep an eye on the kilobyte size of your email. Consider minifying your email HTML. Email minification is one of a handful of automated email production workflow solutions offered by Osmosys. I hesitate to mention my own product in this article, but I am not aware of any other providers who offer automated post processing HTML minification that is tested to ensure content rendering is not impacted.

    How do images affect kilobyte size?

    In the context of HTML email size described above the kilobyte size of your email is how many characters are in your HTML file. The characters making up the url of an image are counted the same way as editorial text, or CSS styles. Be cognizant of when you should use images to enhance your newsletter content. Images are blocked by some email clients by default – you should not assume all readers will see your images. If you have very important information, include it in text as well. Some level of controversy exists in the email world over whether having too many images can cause your email to go to spam. Historically spammers would use images to circumvent spam filters, placing spam trigger words in an image (sneaky!). Today technology has advanced in this area on the spam filter side; even so, sending an email with only images is not recommended.

    Making email better through collaboration, an invitation

    Email can be just as frustrating as it is effective. I am so grateful for and humbled by the many smart collaborators in the space that continually bring issues (and solutions!) to my attention.


    Please reach out (via email, of course at hello@thebyline.co) telling us your newsletter pain point(s), or something you’ve learned that you’d like to share. We’ll answer it here!

    Ready to put all this advice into action? See how Pico can help you build your audience business – from high-converting email popups to fully featured membership landing pages.

    Learn more about Pico

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