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

Ali Rodriguez


in Employee Email

Once a necessity for mass internal communications, mail merges are no longer an effective solution for personalizing employee emails. Learn how to easily personalize mass internal emails with a modern internal communications tool like ContactMonkey.

In today’s business climate, it’s safe to say no one should still be using Microsoft Word’s mail merge feature for their internal communications. Besides being tedious and slow, mail merges can cause numerous errors when you’re trying to personalize employee emails.

After having a laugh at some of the worst mail merge fails we’ve ever seen, we’ll explore a modern solution for personalizing your internal communications. ContactMonkey is an easier and faster way to create, personalize, send, and track HTML emails and internal communications in Outlook.

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The Worst Mail Merge Fails We’ve Ever Seen

Mail merge fails come in all shapes and sizes. Some instances of mail merge not working in Office 365 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”

Email personalization helps internal communicators sound more human, which helps increase engagement with your internal newsletter. Mail merges for Outlook let you personalize your email newsletters easily, so it’s no surprise that many internal communicators rely on mail merges..

But when merge fields go wrong—as they often do when you’re not using the best mail merge tool for Outlook—it has the exact opposite effect and can make your employees feel like just a number.

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:

Re: Policy Number: 647-377

Life Insured: Jack Armstrong

Dear Mrs. Armstrong

We are sorry to learn of the death of {{First Name}}. Please accept our deepest sympathy for your loss.

The beneficiary of the policy listed above is you, {{Relationship to deceased}}. Please send the following paperwork so we can pay your claim as quickly as possible.

  • A certified death certificate that shows the cause and manner of death.
    • A certified copy is a copy that has a raised seal and guarantees that it is the true copy of the original document.
  • A signed and completed death claim form.
    • Complete the W-9 section of this form with your tax identification number, which is usually your social security number. We need this information if we owe your interest on your claim.

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?

Mail Merge fail cat image

Next time you’re about to send an important mass email maybe preview your internal emails to avoid mail merge not working in Outlook?

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—caused by mail merge not working in Office 365—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 email rendering issues can still occur 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.”

Fortunately, 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, no mail merge errors.

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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 Outlook mail merge 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:

The biggest shame—had the merge fields worked—is that 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 because of a mail merge error, I just ignored it.

Mail merge fail #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 current clients about mail merge errors. They have important distribution lists to contact but the moment it’s time to mail merge for Outlook, they find mail merge not sending their emails or mail merge not working entirely.

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; this is mail merge not working in Outlook.

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—if you’re not using the best mail merge tools for Outlook.

Wouldn’t it be great if there was a tool that let you create beautiful HTML emails without having to search for HTML files? Wouldn’t it be nice if you never had to worry about mail merge not sending emails ever again?

Fixes For Most Mail Merge Fails

Even though some of your mail merge issues may be unique to your organization, the majority of mail merge fails can be avoided altogether. The way we know to send perfect mail merges every time is to use the best mail merge software for Outlook like ContactMonkey’s internal communications tool:

Fix #1: Create better internal emails with an email template builder

When designing an HTML-based internal email, you can avoid mail merge altogether by using a dedicated internal email builder.

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

Build beautiful HTML email templates featuring videos, images, surveys, custom icons, and more using our email template builder. Embed animated GIFs into your Outlook emails to grab your employees’ attention. 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:

Screenshot of sample process email created with ContactMonkey's email template builder - mobile view

With ContactMonkey’s email template builder, you can design and send great-looking, responsive HTML emails to your distribution list with ease. This simple fix makes ContactMonkey one of the best mail merge softwares for Outlook.

You can even use ContactMonkey to create your own distribution lists easily using our List Management feature. Build custom distribution lists—without having to wait for IT approval—that integrate with your Human Resource Information System (HRIS) like Workday and ADP, as well as Azure Active Directory, so they’ll automatically update as employee join and leave your organization.

Needless to say, ContactMonkey removes the frustration of mail merges in Outlook and gives you more control over your internal communications creation, sending, and tracking.

See ContactMonkey in action

Fix #2: Test Your merge fields to catch any errors

Using ContactMonkey, you can easily test your merge fields to make sure they work as intended.

With our “Send Test” 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: Supercharge your email sends from Outlook

ContactMonkey integrates with Office 365 and Outlook to allow you to send emails in the background. Never worry about Outlook interrupting your workflow or crashing while sending.

One of the biggest impediments for mass emails in Outlook is its sending limits. Outlook limits users to just 10,000 emails per day, and limits recipients for a single email to just 500 people. If you work at an organization with more than 1000 employees, these limits can seriously impede your internal communications.

Fortunately, ContactMonkey can solve this problem. With our Email at Scale feature, you will no longer be restricted by Outlook sending limits. Send more than 10,000 emails per day, and 16 times faster than sending with Outlook alone.

Emails employees want to open

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 instances of mail merge not working in Office 365—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; and what’s worse, it could have all been avoided by simply using a proper mail merge email software.

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:

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