It’s interesting to manage an email marketing software company – where our customers create and send email campaigns on a regular basis – and then watching and exploring how our team works with the spam messages that return from certain campaigns.

There is a lot to this – and with many companies, we’ve noticed that the legal department can get in the way of delivering emails that have the opportunity to not only get delivered to the inbox but also get read and have the ability to “earn the clickthrough”.  The degradation in results is stunning… like 60% LESS deliverability when legal gets involved with statements inside the emails going out.

But that’s not all.  Many marketers are settling for crappy results, and in settling for those results, they’re also justifying that it’s the “best they can get.”  How low are you willing to set the bar?  Given this state of affairs, there is a LOT of potential to kick butt with email – just call on your creativity and commitment to make a difference with the campaigns that get sent out… too few marketers are doing this, and have gotten lazy and operate by rote about how they send email campaigns (yep, I’m laying down the challenge!).

Let’s dive in…

Backing Up My Deliverability Claim – a real world example…

I want to share with you a recent trip I took down the rabbit hole on a campaign that went out that ended up getting very low deliverability and lots of spam notices.

I’m not talking about the email being reported as spam by a recipient – most recipients never saw this email.  I’m talking about the receiving mail server (MTA, which stands for Mail Transfer Agent, if you’re curious) rejecting it due to what it determined was spam content in the email.

Not all MTAs rejected it – but after being alerted to this by our spam monitoring team, I wanted to dig into it a bit to see what was causing it – and see if there were tools that could have “predicted” the poor response this email actually received.

Down the Rabbit Hole

I reached out to the account holder and started a bit of a conversation with them, and they granted me access to view the email(s) in question – turns out they were a nurturing sequence of three emails – all very similar in nature, and all attempting to sell a product.

They wanted to know what constituted the spam content.  I was curious as well – so I went in search of tools that would identify any issues in the CONTENT of the email itself.  That is very different from email deliverability tools – which primarily look at the sending server IP address, and DKIM/SPF considerations – all technical in nature – but that’s from the old school thinking that delivery is all about the sending server and not about the content.  

Modern email deliverability is not an either/or proposition.  It’s more like a both/and proposition – yes, you need sending servers with a good reputation.  And you also need good content.  That gets pretty subjective – but there are things to explore that get you in the game – and that is what we are going to look at – and contrast those results with the typical deliverability scans that most people utilize.


Well, it’ll be super interesting if you’re interested in getting real results from the emails  you send.

OK – so image #1 from the tool that I used simply looks at the words in the email (not those that are really images – these are words that are in the text of the email itself).


Image 1 – Initial Email Copy – Content Quality

In this image, you’ll see the words on the left, and the rating on the right – overall score for this content is POOR.  The tool is looking at different types of words that would fit into 1 of 4 categories: Urgency, Money, Shady, and Unnatural.

Shady Words:  In the image above, there is only one “shady” word, and that is “save.”  it’s highlighted in pink in the image.  How might you use a different term and yet communicate the same idea?  It may take some creativity – but pull out the thesaurus if you’re searching for possible replacements.

I used a different email to see what would pull up with that one, and shady words are fun ones, and rewriting can actually be a terrific challenge – yet communicate the same idea.  Here are other words that get marked as “shady”:  “get”, “great deal”, “offer”, and “save”.  Here’s one that I never would have thought about –  it caught WON (from the contraction “won’t”) – and until then, I have never considered contractions potential to be caught in a spam filter – so I share that here in case you never did either.

Unnatural:  solution – yep, that would be corporate-speak for sure!  As a business, we’re all about solutions, right?  But it’s not natural in the context of what is getting discussed here.  How could this be rewritten to communicate without using that word?  Kind of fun to play with!

Urgency:  I get it.  You want people to ACT – and in the content, there are three of them:  “ACT NOW”, “limited time”, and “buy”.

Money: “$400” (twice) and “OFFER” (all caps, for some reason the other lower case one landed in the “shady” category).

What About All The Legalese?

In looking at the email – that had two images with more words in them – and a link as a “click to call” – direct to a phone number, there was also a TON of legalese, so I thought I’d see what that does to the overall score.  Check out image 2.


Image 2: Legal copy inside of an email can be the “kiss of death” with qualifying as spam and impacting deliverability.

So I pulled just the content required by legal into the checker.  And it also got an overall score of POOR.  But exponentially worse!  Not helpful.

Not surprisingly there are no Money words in this content – but there are plenty of Shady, Urgency, and Unnatural ones.

Starting with unnatural – there are three:  “Warranty” and “home” (twice).

Urgency includes “click here”, “ONLY”, “only” (twice), and “immediately”.

Shady Words:  Those marked “Shady” had the most (which makes me laugh as this is written by lawyers), and they are: “Limited”, “please” (twice), “not intended” (twice), “life” (twice), “open”, “medical”, “avoid” (three times), and “All”.

Where Will This Email End Up?

OK – so next, I sent a test send – to see where this email landed – and it landed in (drum roll)… in my SPAM folder.  Our domain email uses Google’s GSuite, and I will note now that Google gmail delivers over 60% of all email – so it’s likely that a good number of these emails went into the recipient’s spam folders (where they were not seen at all).

What are the options for correcting or changing this campaign to make it more effective?

First, we could try to change the problematic words and increase the score of the email content.  To do this, I replaced the flagged words with other synonyms… a bit of rewriting, and now it gets a score of GREAT.  (see image 3).


Image 3: Revised Email Copy.

But, will this bring it out of the spam folder?  That’s what I checked next – just using this text – not including the legalese text (since I’ve not cleaned that up – and that is more problematic given it was written by legal – so for this test, I’m going to exclude it entirely).

Results from Testing New Content

I cloned the email and put in the new content that got the overall score of “Great” – and did a test send.  Went into Spam folder.  BUMMER… but I also noticed that the alt tags for the images had more spammy content in them.  So I removed that content with non-spammy yet same meaning – similar to how I changed the copy.

Then I did another send. Into the Spam folder.  Darn it!

So – I remembered what we discovered several years ago, and have taught to thousands of marketers, there are THREE factors that determine deliverability:

    • Sending server IP reputation
    • Email copy/content
    • From email address

So, I went in and changed the “from email” to my email address (which has a good sender reputation), and From text.  Sent again (to a different Google Workspace hosted email address), and… drum roll… it landed in the INBOX!  Not the updates or promotions tab, but the primary inbox!!

One Final Note on Deliverability Tools…

Those tools that test for deliverability – but mostly look at the technical details like sending IP Address reputation?  I ran through those tests also. They all gave the ORIGINAL email flying colors and said it was just fine.  So bear that in mind when selecting which tools you pay attention to – because even though they passed with flying colors – that email went into the SPAM folder (at least in Gmail/Google Workspace, which delivers 60% of all domain based email, remember?).  Just a word of caution on this.

When I originally looked at the content and shared that it got a POOR score – the response from our customer was that it tested just fine in the tools they were using.  Which is why I bring this up… and what had me run through what I outlined above.  For me, it’s all about TESTING, and observing – it’s how we’ve built fundamental best practices around email marketing – because we look at the data, and then start exploring creative options, to see what works.

Most email marketers are running as fast as they can to get the campaigns out the door – no time to do this sort of due diligence – I totally understand that as well.  But… If spending a bit of time checking this and applying a little creativity to the email copy can have 60% more of your recipients actually SEE your email, how many more clicks might you get?  Would that be worth it??  Could you double your clickthroughs?  Triple?  Of course it all depends on what the click goes to and how compelling it is to click… but it sure is worth considering!

The benefit of tackling this and challenging your copywriting skills?

How about getting 60% MORE emails delivered to the inbox?  If you’re happy with the results from having MOST of your emails go into the ether (i.e. spam folder) — never to be seen by a recipient, and damaging the sending IP reputation as well as burning your from email address’ reputation – then ignore this blog post and the call to action to challenge yourself. 

If you’d like to actually see what might be possible – and not blame the medium (in this case email) – then take this on and see what you can create!  I prefer paying attention to data and always striving for better results, than settling for mediocre results and thinking it’s the best that can be accomplished.

Creativity requires thinking through the campaign

I can hear the thinking about legal and their copy.  If you need legal copy — then rethink how you use email.  Take the user to a landing page – and put your legalese on the landing page — keep your email doing it’s job – and stop trying to have email do everything — it DOES cost you, and potentially A LOT.  I’m sure there are other great options as well — but that’s one that could be accomplished pretty easily.

Could your email campaigns be improved?

This brings me to my last question for you.  Are you happy with your email results?  Or are you merely resigned that you’re getting the best you can from email since there’s so much in the inbox you’re competing with (which is a cop out for any serious marketer)?

If you aren’t getting the results you would love and/or need to get from your campaigns – and would love some analysis and creative thinking based on solid email delivery fundamentals, get in touch with us – we might be able to help!