Troubleshooting problems with email deliverability is typically the responsibility of your IT department. Email deliverability problems can have a variety of causes and require complex, multi-step solutions.
As a senior leader in your organization, you might not have a ton of transparency into the root cause of the issue and whether or not your IT team has the skills to resolve it.
This article walks through the questions to ask IT about email deliverability in order to gauge whether your people have the necessary knowledge and skills on board including:
Before we get into the questions to ask your IT folks and red flags to watch out for, let's cover some basics.
Email is one of the primary modes of communication for associations, along with your website, community, etc. Associations often need to send large numbers of emails, both internally and externally, to communicate with members about all kinds of projects and events.
Being able to describe your value proposition to your constituents (donors, members, etc.) is super important. Ensuring that your communication hits their inbox is paramount to executing strategies for the organization.
If your emails aren’t being delivered properly, that’s more than a nuisance. It can be a huge obstacle to the success of your initiatives, events, and ultimately your member engagement.
Not tracking and responding to unsubscribes, bounces, and other unfavorable responses can surely create email deliverability ordeals that can plummet your metrics as well as the authenticity, reliability, and size of your contact lists.
But what happens when you get marked as spam or stuck in a spam trap? Enter an organization’s worst nightmare: the blacklist, aka a black hole that you may never climb back out of.
A blacklist is a collection of IP addresses of email senders that have been flagged by one or more spam filters in email service providers (ESP's) like Apple Mail, Gmail, and Outlook. These senders are believed to email out malicious, unwanted, or suspiciously “spammy” content. Spam filters respond by blocking these IPs entirely or routing their emails to the garbage can: the spam/junk folder.
Problem is, legit senders sometimes get incorrectly blacklisted because they haven’t properly set up their email domain records (which we’ll describe in a minute) to identify their organization as a valid sender. So instead of your emails landing in recipients’ inbox, they could get stuffed away as spam, likely never to see the light of day again.
Regardless, getting blacklisted is NOT something to take lightly. During the dreadful (and potentially permanent) time you’re scarlet-letter branded and shunned to the “naughty list”, you risk:
Long story, short: you need the right technology and settings in place to protect yourself and your brand from the dangers of poor email deliverability, list hygiene, and domain reputation.
So, what should you ask your IT team to quickly figure out what the problem is and if it’s being solved? Here are the high-level questions to ask IT about email deliverability when your association is having trouble with your delivery and sending reputation:
It’s important to ask your IT staff if they fully understand the rules and methods for authentication of your domain in order to ensure your emails are being delivered properly.
On a high level, there are three authentication methods that should be set up to ensure email deliverability.
A tool like Google’s Messageheader helps you determine if these records have been set up properly. You can grab header text from an email that’s previously gone to spam and analyze it.
There are nuances that can have major effects as well when you dig deeper into these email records. For example, using a tilde instead of a hyphen for an SPF record affects how valid senders are authenticated. As a CEO, you probably won’t get to that level of detail, but you should be able to ask your IT folks, “why is this done in this format” and receive an acceptable response.
A number of tools exist today that can help you analyze the emails you send to see if you’ve been blacklisted.
These tools are designed to sniff out potential spam violating criteria and unsolicited bulk email per CAN-SPAM Act and similar regulations.
A few of the monitoring tools we recommend include:
However, keep in mind that there’s another layer of complexity at play here. Some email systems use AI and advanced algorithms that may mark emails as spam even when everything is “set up correctly.”
Again, there are just so many nuances and restrictions when it comes to checking email validity, especially for these organizations that are leveraging email automation instead of using all IP addresses for the human, everyday stuff.
For example, at Cimatri, we rely on automation to determine the importance of emails sent to us, so sometimes recipients are required to indicate that the organization and domain they’re receiving from is valid. We use our personal emails for that.
Your IT department should have a comprehensive list of any application or tools used by all departments that send email. This could include software used by a wide range of departments, from marketing to accounting. It’ll likely be a long list if it’s truly complete.
Many applications rely on email, and it’s important to understand how they’re being used and include them in this master list.
Email applications often track and display metrics on spam issues, bounces, unsubscribes, and click engagements so you can measure whether your email efforts are producing the desired result. It’s important to understand what metrics are available and that someone is keeping an eye on those metrics.
For example, if you’re sending emails through WordPress, the system may or may not be sending these communications through an authenticated address. Your email metrics should give you this insight so you can correct the issue to ensure deliverability.
Your email lists should only be made up of subscribers who have physically signed up for your newsletter and/or email campaigns. If they unsubscribe, you should have processes in place to automatically remove the email address from your list.
Double opt-in (also called confirmed opt-in) is the email permission standard today. This requires the subscriber to click on an email confirmation link to verify their email address and subscription to your email list.
You also want to perform regular list hygiene or list management practices. This entails removing hard and soft bounces, bad or fake emails, and inactive or unresponsive addresses from your email list.
If you’re not regularly cleaning out your lists, you could be penalized. You can also easily email a spam trap on accident and get automatically marked as spam.
Or you can get physically marked as spam by actual users who have unsubscribed but are still receiving your email communications. All of these situations can put your IP address and email domain on that dreadful blacklist.
Bonus Tip - While this isn’t a list hygiene best practice, make sure you’re also responding to email list preferences requests (e.g. frequency or type of email) to keep your email contacts happy and engaged!
Is any staff member or department using an internal mail server? If so, is it on a dedicated IP or shared IP address? Shared IP addresses are public configurations that affect both the entity using it and anyone else sharing that service.
Make sure your IT department understands how shared and dedicated IP addresses work, the systems your organization uses, and how to set up the records accordingly to ensure deliverability. It’s also important for IT to understand how everyone is connecting with members and vendors, both in and out of the office.
Your IT team should be able to outline the risks associated with your organization’s email decisions and provide mitigation steps to your marketing teams and whoever else may be managing and cleaning your lists or, shudder to think, sending mass emails. And, as always, be sure that the email content you’re sending organization-wide is relevant to the receiver to avoid spam issues.
There are tools that allow you to test if records are properly set up prior to sending those emails. Be sure your IT team has checked these tools and run tests to determine the reliability and validity of emails being delivered through different systems.
Here are some warning signs that should raise the caution tape.
If any of these ring true, then it could indicate some communication and alignment issues within your IT division, or that you simply need to engage an email deliverability expert to get the clarity and remedies you need right away.
Basically, if your IT team can’t provide a consistent answer as to why email deliverability isn’t working for your organization and a clear remedy with a timeline, it’s time to engage outside help.
If your domain has been blacklisted, you’ll need outside professional help because getting it resolved, if at all possible, typically requires a significant amount of time, technical know-how, and direct communication with the database(s) that have blacklisted your IP address to verify that you’re indeed not sending spam.
The remedy won’t happen overnight, but regardless, you’ll want to gather information from specialists on the solutions available to you based on your specific situation.
Seeking outside expertise is critical when you’re caught in this situation because a specialist will be able to succinctly tell those databases what they need to hear in order to fully authenticate your domain and remove your blacklists as quickly as feasible.
If you need help getting your email deliverability questions answered and issues resolved in a timely manner, get in touch with us here.