Internal Communications

The Worst Mail Merge Fails (and How to Fix Them)


By Ali Rodriguez


From the bad, to the ugly, to the downright embarrassing: we’ve compiled a list of some of the worst mail merge fails we’ve ever seen. Why? Because it’s hilarious.  But also because it helps show why getting mail merges right is so important.

If you’re using Microsoft Word to send a mail merge or a personalized employee newsletter with Outlook, it can sometimes be the stuff of nightmares. You just know that mail merge fails are coming.

Let’s have a laugh at some of the worst mail merge fails we’ve ever seen. But don’t worry, we’ll also explore how to fix them with ContactMonkey: an all-in-one internal communications tool that let’s you create, send, and track HTML email in Outlook and Gmail. Book a free demo to see how to send mail merges the smart way.

Why not use a modern internal comms tool today?

Start a 14-day trial. No credit card necessary. Zero risk.

Try Now

The Worst Mail Merge Fails We’ve Seen

Mail merge fails come in all shapes and sizes. Some fails have minor consequences, but others can have monster consequences. Make sure you’re sending out your best content by using a dedicated internal email tool.

Mail merge fail #1: “Dear {First_Name}, we’re sorry for your loss”

We’ve talked about personalization for years and we will never stop. Personalization helps internal communicators sound more human, thus increasing engagement with your internal newsletter. It’s a no-brainer: the best mail merge software let’s you personalize your email newsletters easily.

But when merge fields go wrong, it has the exact opposite effect and can make your employees feel like just a number.

The worst case of a mail merge gone bad

When tragedy strikes, there’s at least the comforting reassurance that our insurance company has our back. But what happens when their heartfelt letter regarding life insurance messes up every single merge field in the letter? The result is something like this:

mail merge fail

Luckily, most of us in the internal communications field won’t really have to deal with life or death situations, but important information like a change in leadership or an update in the benefits package deserves thorough attention. The last thing you want is to send out leadership communications riddled with errors!

Mail merge fail #2: sending a cat picture instead of a meeting invite

Don’t you hate it when you’re trying to send a meeting invite and accidentally send the cutest picture of a cat?

Next time you’re about to send an important mass email maybe preview your internal emails?

Mail merge fail #3:  visuals are great…broken images aren’t

Great visuals can take a boring email and make it compelling, increasing employee engagement and click-through rates, but broken images actually cause the opposite effect: they impact your credibility and lower the likelihood of your employees ever opening one of your emails again.

As Outlook users know, even if you’ve done everything correctly, Outlook will mess up your HTML, responsive templates because Outlook wasn’t really built to be responsive.

Take this comment on a Litmus’ forum about responsive emails breaking in Outlook: “There’s no way, to my knowledge, of stopping this. Outlook doesn’t use HTML as a rendering engine, instead creates a mail merge in Word. So HTML gets altered when used in Outlook.”

This might sound ominous, but there’s an easy fix. With ContactMonkey’s email template builder, you can create and send responsive HTML emails within Outlook featuring your company newsletter ideas. No fuss, no problems.

Let us show you the power of ContactMonkey.

We can make your life much easier. Let us help you now.

Book Demo

Mail merge fail #4:  personalization gone wrong for every merge tag

Mail Merging with personalized merge fields is amazing when it works. Being able to make hundreds or thousands of emails sound like you personally wrote them is a technological blessing. However, when it goes wrong like in the example below, you just assume that whoever sent it doesn’t care about you at all.

This is an actual email I received not too long ago:

mail merge fields

The biggest shame is that, if the merge fields would have worked, I would have probably taken an action. The email is perfectly written and they do seem to have something to offer. However, since, the email was all messed up, I just ignored it.

Mail Merge #5: Spending 4 Hours Trying to Send an Outlook Mail Merge


The example above is one that we’ve encountered many times in our conversations with our now clients. They have important distribution lists to contact but the moment it’s time to mail merge, they’ve now entered an inescapable, messy maze.

One user in a Microsoft forum showed how frustrating it can get: “300 person Mail merge took 15 minutes to run … is that normal?”

No, it isn’t.

Mail Merge Fail #6: Having to Leave Your Inbox

You’re sending a mail merge from your email address; why should you have to leave your inbox? Keeping track of your HTML files across different platforms can be a pain. You can easily lose track of your created mail merges, adding even more time to this already lengthy process.

Wouldn’t it be great if there was a tool that let you create beautiful HTML emails without having to search for HTML files?

Fixes For Most Mail Merge Fails

Even though some of your mail merge issues may be unique to you, the good news is that the majority of mail merge fails can be avoided altogether. The best way we know to send perfect mail merges every time is to use ContactMonkey’s mail merge functions:

Fix #1: Email Template Builder

Remember how painful it was to send a somewhat nice-looking newsletter or a simple email message to a distribution list using word mail merge?

With ContactMonkey’s drag-and-drop email template builder, which you can access from your menu in Outlook, you and your team can create perfect emails without any developer or design skills:

email template builder - mail merge fails

Build beautiful HTML email templates, featuring videos, images, animated GIFs, surveys, custom icons, and more using our email template builder. You can easily include regular pulse surveys in your employee emails using ContactMonkey’s employee pulse survey tool.

You can rest assured knowing that your HTML emails will appear perfectly across all devices using our Preview option:

With ContactMonkey’s email template builder, you can design and send great-looking, responsive HTML emails to your distribution list with ease. Don’t use distribution lists? Easily learn how to create a distribution list in Outlook in seconds.

Fix #2: Test Your Merge Fields

With your ContactMonkey Internal Comms tool you can easily test your merge fields to make sure they work as intended.

With our “validation report” you can instantly see from within Outlook how your inserted merge fields are performing. If everything is working right, your fields will appear green and if there’s anything broken, the merge tag will be highlighted as red, allowing to fix the entry value before hitting send.

Once everything looks right you can hit our preview button to make sure your mass email or internal newsletter looks as intended.

Fix #3: Send from Outlook

Our Mail Merge feature built for Office 365 sends emails in the background so you never have to worry about Outlook interrupting your workflow or crashing while sending:

merge fields for personalized emails

By leveraging the power of the Office 365 cloud, once you hit send, your mail merge sends in the cloud, and you can go back to work with the certainty that your emails will look awesome. Just make sure your emails don’t exceed the Outlook email limit.

Before, even selecting your recipients and preparing your contact lists could take you ages. Now with the simple click of a mouse you can select your distribution lists or simply upload a CSV—all without leaving Outlook!

Test ContactMonkey right now. You will love it!

Start a free 14-day trial. No credit card is necessary.

Try Now

Mail Merge, the Smart Way

Although some of these Outlook mail merge fails aren’t your fault, the fact that there are better ways to do things should at least get your attention.

All joking aside though, some of these mail merge failures, if repeated, can have a big impact on your career and your credibility. As you very well know, a bad first impression can last forever.

ContactMonkey is all about giving you the power of HTML emails without any of the headaches. Our email template builder is powerful resource for boosting your email sending game.

Learn how to use an internal communications software to send better emails and get rid of your mail merge pains. Set up a free ContactMonkey demo and we’ll help you out right away:

Want to improve your internal communications and employee engagement massively?