Don’t Take A Chance On Going To Email Jail

March 28, 2017 10:09:27 AM | By Matt Benati

If your marketing automation system indicates your emails went through, then it’s time to focus on engagement and open rates, right? Focus on writing subject lines that get clicked, email previews that generate opens, and creating content and offers that your prospects won’t be able to resist.

But what if your emails aren’t actually being delivered? Deliverability is a hidden issue often controlled behind the scenes by spam filters, your sender reputation, the content and timing of your email, and the different algorithms deployed by major email service providers like Google, Microsoft, etc.

Whether you know for certain that you have deliverability issues, or you just want to make sure you’re checking all the right boxes, here are some secrets to increasing email deliverability rates:

Don’t Get Flagged As A Graymail Sender

Even if people have opted in to receiving your messages, if they never open them, you could be flagged as a graymail sender.

Graymail is email a person opted in to receive, but doesn’t really want. They may have given you permission to email them because they wanted a juicy piece of gated content or a special offer. But, if they never open any of your future mailings, their Internet Service Provider (ISP) will notice. The result? Your future emails wind up quarantined. Never actually delivered!

Your graymail recipients won’t see your emails any more, and what’s more, servers tag senders of graymail. This means that even brand new subscribers who are on the same server will block your emails. You can avoid graymail penalties by establishing proper timing and frequency of your emails.

Optimize Send Times

Because user engagement directly affects your deliverability long-term, it’s important to send your campaigns at times when your recipients will open, click and engage with your content.

You can accomplish this in a number of ways that all have varying degrees of success:

  • Testing and optimizing the send time for particular segments, personas or audiences as a whole.
  • Capturing time zone or zip code information and using this to segment your lists to deliver at a specified time within the contact’s time zone. Some automation systems do this automatically; for example, HubSpot has a “Smart Time zone Sending” feature to adjust sends based on time zones.
  • Using software that customizes the send time for each individual.

With the first point, it’s all about trial and error; carefully analyzing your email marketing statistics and systematically determining the best send times for each segment.

If you have an audience that spans multiple time zones, the second point is a great step toward optimizing your send times. However, it’s important to understand that there is no silver bullet or “one” best time to send email to your audience. Some contacts may begin work at 8:00am while others have been up and checking emails since 5:00am. Additionally, capturing accurate time zones can be tricky as VPNs and proxy servers may be located in different parts of the country (or world!) from where your recipients are actually working.

Using software that customizes the send time for each individual is often the most effective as it:

  • Increases overall engagement, which will help with long term deliverability
  • Decreases bad unsubscribes
  • Throttles emails so that it doesn’t trip corporate SPAM systems
  • Keeps contacts engaged
  • Empowers you to pause and restart campaigns if something is wrong with the email. For example a bad link, broken image, wrong webinar date or an out of stock sale item that is being promoted. With traditional batch and blast methodologies, the email has already gone out to the ENTIRE audience so there is no way to limit the impact.

Determine Optimal Email Frequency

The frequency with which you send emails can be equally important. Some people will read whatever you send them on a particular subject, and some people only want to read about it once a month. If you’re constantly sending out new content, the latter group will tune you out and you’ll be at risk for a graymail penalty. Even the most loyal customer can experience brand fatigue at some point if you’re not paying attention to their buying patterns and engagement with your email messages. Using artificial intelligence, brands can track and analyze these habits to determine optimal email frequency.


Email server authentication is a large and complicated topic, so we will not go in depth here. Suffice it to say, authentication is a critically important part of email marketing that many accidently overlook as it can be quite intimidating to configure correctly and often involves IT support. The authentication process verifies a server’s identity, giving receiving servers assurance that the message is coming from a reputable source.

Ensure that you limit complicating factors like different reply-to domains and properly configuring your DKIM records will help with long-term deliverability.

Promptly Address Manual Unsubscribe Requests

Rather than clicking ‘unsubscribe,’ some recipients simply reply to your emails requesting that you remove them from your email list. When left unchecked, these recipients will stop opening your emails, or, worst case scenario, leave unflattering online reviews that damage your brand’s reputation. Since a decline in open rates can result in graymail penalties and affect future deliverability, it’s important to monitor your campaign reply emails and promptly act to remove unsubscribes from your email lists.

Keep Your Database Fresh By Removing Expired Email Addresses

With as many as 30% of people changing jobs annually, database decay in an unavoidable fact of life. If you continually send to expired email addresses, you’ll receive hard bounces and your sender reputation can be negatively impacted. According to Oracle, “high hard bounce (invalid) rates are the fastest way to trigger filtering and blocking on your new IP.” To keep your database fresh, continually monitor your campaign reply emails to identify changes in contact information.

Don’t Ignore Valuable Left-The-Company Emails

When a person leaves the company, their email address often expires after a certain amount of time. Prior to this expiration, many organizations set up Left The Company (LTC) auto-replies to let senders know of the change and provide them with the new primary contact’s information. If you’re not monitoring your campaign reply emails, you may not know about a LTC and will continue unknowingly sending to an expired email address. Over time, this can affect your sender reputation and result in all your emails to an organization being blocked or quarantined.

Stay On Top Of Sender Verification Requests

Many organizations employ a Sender Verification process when receiving emails from a new sender. These require you, the sender, to do something prior to your message being delivered. If you miss the email prompt with the verification instructions, your message will never make it to the inbox. Again, monitoring your campaign reply emails is critical to seeing and acting upon these requests. Ignoring them damages your sender reputation as it appears emails are being sent from an unmonitored address.

Additional Issues That May Affect Deliverability

A few parting points on deliverability and why you may still be struggling with your messages reaching recipients:

  • You’re being flagged as spam – If you’re doing everything mentioned in this post and still getting flagged as spam, make sure you’re in compliance with anti-spam laws.
  • You’re sending attachments – Because many cyber attacks occur via attachments, understand that if you choose to send attachments, they may get filtered and blocked.
  • You’re using a shared IP address – Some email automation solutions have shared IP addresses for their users. If one user gets blacklisted, others may have deliverability issues.
  • You practice Account Based Marketing strategies – If you’re a B2B, and especially if you employ an ABM strategy, you face the added challenge of sending to multiple people within the same organization and upping your risk of being filtered. Having an ABM email delivery strategy addresses these deliverability issues and ensures your messages are getting to their intended recipient.

While email marketing is still an invaluable tool to today’s marketers, it’s important to understand the many factors that affect deliverability and specific steps you can take to ensure your messages are hitting as many inboxes as possible.

Co-authored by Mike Donnelly, CEO and Founder of Seventh Sense, and Matt Benati, CEO & Co-founder of LeadGnome.

Seventh Sense is a data mining and artificial intelligence system that helps sales and marketing professionals optimize the send time and frequency of email outreach using a collection of best-of-breed cloud and big data technologies to automate the process of gathering and analyzing data. Learn more and request a free demo at

LeadGnome is an Account Based Intelligence web service that mines reply emails to grow pipeline and increase sales velocity by generating new contacts, providing actionable sales intelligence, and enhancing existing leads. Learn more and start your free trial at

If you’relooking to up your ABM game, try LeadGnome for free and see how easy it is to start mining your emails for Account Based Intelligence today!

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