Oops-Proofing Your Emails Like a Pro

Email mistakes happen; when they do, they’re often more than just a typo. A broken CTA, a missing subject line, or an email sent to the wrong list can cost clicks, conversions, and trust. We’ve all been there. That’s why we kicked off the year with a webinar dedicated to dodging disaster, building better QA processes, and bouncing back when things go sideways.

This session brings together a powerhouse panel of email nerds who’ve seen it all (and survived to tell the tale). Below is the transcript, lightly edited for clarity and flow.

Emily Santos: Hey everyone, welcome to our first webinar of the year! We're starting strong with a topic every email marketer knows too well: mistakes, and how to avoid turning a small slip into a full-blown “oops.”

Joining me today is a stellar crew of email pros:

• Matt Helbig, Integrated Marketing Manager at RGE and Beefree, and our go-to expert on what not to do in email.
• Mary Shoemaker, Director of Marketing at Sherry Hill Programs, here to share what happens when email errors hit at scale and how to recover.
• Bettina Specht, Product Marketing Lead at Beefree, who lives and breathes the QA tools and workflows that help catch mistakes before they go live.

And I’m Emily, your friendly Creative Overthinker at RGE and Beefree. I’ll be your host, guide, and professional button-hoverer for the next hour.

We’re diving into the most common email blunders, how to build stronger QA processes, what to do when things go wrong, and why a well-timed apology might actually boost your open rate. Stick around and bring your own horror stories for the Q&A at the end.

Let's start with a game called "Would You Rather."

Would you rather send an email with a broken CTA or send an email with a typo in the subject line?

Mary Shoemaker: This is easy. I would take the embarrassing typo because here's my thought: That embarrassing typo will make them open the email. And obviously, a broken CTA—that's just about as bad as it gets in my book.

Matt Helbig: You could try to play it off as intentional. However, a thousand people clicking on a 404 link keeps me up at night.

Bettina Specht: Yeah, I'm with you. Someone said in the chat, "No, CTA, no party." I take the typo as well.

Emily Santos: Most people will prefer their embarrassing typo.

Would you rather accidentally send a draft version of an email or send an email to the wrong list? This one is tough.

Matt Helbig: I'm going with the wrong list. It's still the right message, just a surprise list. Will there be some bonus clicks out of curiosity?

Emily Santos: Yeah, this one's about 50/50. More people prefer to send a draft version of an email.

Would you rather have your boss catch your mistake first or have a customer call you out on Twitter?

Mary Shoemaker: This one's easy for me. Have your boss catch your mistake first. If your boss is good, and you're a team, right? You can manage that together.

Matt Helbig: All press is good, but I'd rather my boss catch it—ideally before it hits the inboxes of 100,000 people and a Reddit thread follows.

Bettina Specht: Hopefully, a boss will catch it before you hit the send button.

Emily Santos: This one was easy for most people. The majority would prefer their boss to catch the mistake.

If you've had one, what was your biggest email face-palm moment? Matt, do you have one that you'd like to share?

Matt Helbig: Oh, I've got one. I allegedly sent an empty subject line to a million people. It did end up being our most engaged email, so you never know. I've learned from my mistakes. Please do not put anything in the ESP or tool until it's final.

Bettina Specht: I was working on a newsletter while our team was developing a website. They mentioned we could use more testimonials, so I wanted to help. I was focused on the newsletter, so I added a note at the beginning: "If you'd like to receive a coupon, just reply to this email with a few nice sentences about why you love our tool."

I remember joking that if we got a dozen responses, we'd be lucky to extract some good quotes from them. I didn't give it much thought, so I hit send. To my surprise, we received one reply, then two, then three—and soon hundreds.

What happened next was that I ended up giving away a ridiculous number of discount coupons! We got a lot of great testimonials, but it still wasn't that great.

Mary Shoemaker: My biggest mistake was sending the wrong email to a list of about 80,000 people. The email reminded everyone to book their Santa visit, which wasn't relevant since it was January. I managed to recover from the situation, and I’ll explain how to handle such errors, but it certainly wasn’t an ideal experience.

Matt Helbig: We all make mistakes, but the biggest risk is losing trust. Frequent errors like broken links or incorrect lists can damage your credibility and lead to lost conversions. It's important to double-check everything before sending emails, as mistakes can result in financial loss and increased anxiety.

Minor errors can accumulate and undermine brand trust over time. Establishing a solid process to minimize these mistakes is crucial since you only have limited opportunities each year.

Mary Shoemaker: I agree with all that. And it's like your career. If email is your career and you're messing up all the time, that's tough to sleep at night.

Matt Helbig: That's why I love some guardrails. Build a system that catches you before you mess up. Or at least give you a heads-up before you hit send.

Bettina Specht: The stress and fear that builds up within yourself and the team once you've made mistakes are scary. Hitting that send button already is scary, and it gets so much more scary once you've made a mistake. Rebuilding that confidence is tricky.

That MailChimp button was the worst! For those who don't know, it featured a GIF that appeared when you hovered over the send button, asking, "Are you sure you want to send this?" As you hovered, a monkey's finger would start to drip sweat. I always thought hitting the send button was scary enough without that added anxiety!

Matt Helbig: That's why I schedule all my emails. I don't hit send right away. It's always a schedule.

Bettina Specht: Fortunately, many mistakes can be avoided—or at least the risk of making mistakes can be reduced—if you have the right tools and processes.

Now, let's explore the topic of quality assurance (QA) further. First, I want to hear from you: What is your current QA process? Are you just winging it, have a robust QA process, or are you somewhere in between?

The number one rule for avoiding mistakes is always to get a second pair of eyes.

Your brain tends to automatically correct errors, causing you to read what you intended to say rather than what you wrote. Therefore, having another pair of eyes—maybe even two or three—review your work is always a great idea.

The review and approval process is challenging, so the more cooks in the kitchen, the wilder it usually gets.

Mary Shoemaker: I prefer to keep the review process small, involving someone from my team and an outsider who hasn't seen the material before. Sometimes, getting feedback from a friend in accounting who can read your email can provide a valuable broader perspective.

Matt Helbig: This can be a tricky step for me, especially when I'm sending a last-minute, late-night email and no one else is around. It's easy to think, "It's probably fine; we can just skip it." However, having someone on call or nearby to double-check is helpful. Getting that second set of eyes is important.

Bettina Specht: The success of this process hinges on how organized you are in collecting feedback. Feedback from multiple channels—like Slack, replies to test emails, and colleagues shouting edits from across the office—can become quite scattered. While these comments may be intended to be helpful, they often lead to mistakes and can cause you to overlook important feedback.

When considering reviews, it's important to consider who should be involved in the process. Ensure you are not limiting your feedback sources and are clear about how the review process will work. Centralizing feedback in one place is beneficial, and several tools can assist.

If your team already uses project management software for other aspects of your work, consider building upon that foundation.

Alternatively, various tools designed to streamline review and approval are available if you want to focus specifically on the email review process. Some examples include Litmus and Proofjump, which are specifically tailored for email.

At Beefree, we also put a lot of thought into this process. If you're using Beefree, you have access to tools that allow you to collect feedback, leave comments directly on the designs, and gather approvals all in one place. This way, all your input is organized and actionable.

If you have scattered feedback, you sometimes have competing feedback or folks pointing out stuff you've already changed. That, again, adds complexity and additional loops to the process, and it's just frustrating for everyone involved. If that is something you see happen frequently, that is likely a sign that your team and the question of who needs to approve is so big that looking into a tool that helps you consolidate it could make your life easier.

Because we talked a bit about collecting feedback, what should you check for? We'll dive into that because using a pre-send checklist to bring organization and structure into your QA process is always a great idea. Then, you're winging it a little less, and you're more likely to catch those mistakes.

We've put together some things you should check or look out for. First, let's start with what you should check to make sure you're making a great first impression in the inbox. There are a couple of things. First, do you have your subject line and preview text set up?

So don't be like Matt and send a blank subject line to a million people. Second, make sure your "from name" is set up correctly. Sometimes, you may be sending from a person or your brand name, so you should double-check that.

The reply-to address is often overlooked. Make sure that your reply-to email is set up correctly and works because people tend to hit the reply button. If they have feedback or something to tell you, they often don't go through your usual support channels. If your reply doesn't work, you're losing that chance for a conversation.

Matt Helbig: It's important to check how your subject line and preview text appear on an iPhone or other devices, especially if you have a longer subject line. Make sure they aren't cut off in a way that makes them unclear.

Don't make the same mistake I did—triple-check your subject line and preview text. View it from a reader's perspective rather than someone who has seen it multiple times and might assume it still makes sense.

Bettina Specht: Then, this one is more about your content. So, first of all, of course, check for typos. There are plenty of tools out there that can help you. Someone mentioned Grammarly, but it is important to be thoughtful about proofreading and taking the time to do it. So you can catch those typos before they make it to the inbox.

Matt Helbig: I've learned the importance of checking text in images. Sometimes, I read through the body text and proofread it carefully, only to overlook a mistake in an image. For example, we incorrectly spelled "San Francisco" in a prominent hero image, and that error went unnoticed.

If you're working with translations or similar tasks, it's crucial to have a native speaker review the content. Translations can sometimes be tricky, and having an expert double-check can help avoid issues.

Bettina Specht: We've discussed the importance of links in emails. Broken or missing links are among the most common mistakes that seriously hurt your email campaign's performance. It's crucial to take the time to check these links thoroughly.

Additionally, ensure that you have proper tracking to accurately assess your campaign's success. I want to highlight a pro tip: sending an email can be daunting because you can't take it back after sending it. The same goes for broken links; once an email is sent with them, it's challenging to rectify the situation.

However, some ESPs allow you to change links after sending an email. For instance, if you use the built-in link tracking feature of certain ESPs, they can swap out the link redirects in the backend. An example is Salesforce Marketing Cloud, which offers this capability.

Matt Helbig: Anyone who uses link wrapping can usually change that out.

Bettina Specht: Check with your ESP. If you're unfamiliar with something, refer to their support documentation; it could be helpful in the future. Also, make sure that your unsubscribe link is included and positioned correctly.

Additionally, double-check your dynamic content. If you're using dynamic personalization, be cautious to avoid awkward instances like including the wrong content in your email body or subject line. Test the content, and remember to test the fallback options as well.

Matt Helbig: I've encountered problems where a link was dynamically pulled in, but the first part of the URL was already present. This led to issues like the URL doubling up, which resulted in broken links or missing dynamic content, causing the email to either fail to send or send out empty.

It's important to establish well-tested fallbacks to ensure that at least something is being sent rather than sending out something completely broken.

Bettina Specht: This third part focuses on your design. What key elements should you check in your design?

First and foremost, ensure that your design aligns with your brand. Are you using the correct colors? Things could go off track if you're part of a larger team. Verify compliance with branding guidelines and check how your email appears across different clients and devices.

If a significant portion of your audience uses Outlook, especially in a B2B context, or if many are likely to open emails on mobile, it's crucial to test your emails in those environments to ensure they look great. We'll discuss some tools for this later.

Make sure all your images have alt text for accessibility reasons. Additionally, pay attention to their size. We recommend keeping images under one megabyte, ideally under 500 kilobytes, to ensure they load quickly and create a positive impression in the inbox.

Lastly, don't overlook the overall size of your HTML file. Keep it below 102 kilobytes. Gmail has a specific limitation; it clips emails exceeding 102 kilobytes, and you don't want your message to get cut off. Therefore, be sure to check the file size.

Matt Helbig: I use TinyPNG for images and Ezgif for GIFs. Make sure the email is loading quickly, and check it even on a mobile device, like off of Wi-Fi, to see what that experience is like.

Mary Shoemaker: Don't forget dark mode. Things look different in dark mode, which should always be part of the check. Sometimes, colors look nice, but then you put them in dark mode, and they're pretty terrible, or logos get lost, and things like that.

Matt Helbig: Many people are starting to use large language models (LLMs), like ChatGPT, to generate alt text based on images. This means there are fewer excuses for not including it.

Additionally, it's helpful to check the contrast and other accessibility aspects on different platforms to ensure that recipients can read your email before you hit send.

Bettina Specht: The list of tasks can be lengthy. While you can always check everything manually, this can become challenging if you're sending numerous emails. Fortunately, various tools can help automate aspects of the QA process and perform checks for you.

We discussed email previews, and there's also a conversation happening in the chat about how to view your email in dark mode or across different clients. You see a screenshot from Inbox Monster on the screen, but Email on Acid, Litmus, and other similar tools allow you to preview your emails without sending them to countless inboxes.

Let these tools handle the testing so you don't have to. For instance, one notable tool I want to highlight is Beefree Smart Check, which helps identify various mistakes. For example, it can point out if you've forgotten to include alt text for accessibility, if you've missed a link in a call-to-action (CTA), and it also flags any images that may be too large or GIFs over the recommended 500-kilobyte limit. These features are built into Smart Check and Beefree, so I recommend checking them out.

These tools can assist in catching errors once the email is built, but effective QA can begin much earlier. If you establish the proper guardrails from the start, especially in helping your team stay on brand, you can prevent errors during the email creation. This way, fewer issues must be addressed during the review stage.

Strong email design systems are an excellent way to keep your team on track. As teams grow and more people get involved in creating campaigns, often, individuals who may not be email design experts, brands face challenges in maintaining brand consistency. Implementing brand guardrails can help in this regard.

Various tools allow you to set design guidelines and establish rules related to colors and typography, which can assist your team in being creative while staying within the brand's boundaries.

Brand guidelines are essential, and I encourage you to explore the options in your email creation tools that allow you to implement stricter rules around what your team can and cannot do during the email creation process. For example, we permit a content editor to update copy, but that is the only action they can take.

So, if you are scaling your email creation process to a place where you want people to create emails but want to lock their permissions to content updates and copy updates only, but don't let them go wild on colors and other parts of the design, then that is a great way to do that.

Matt Helbig: I agree that locking links and dynamic sections is important to prevent interference. This way, others can only proofread specific parts. If you don't want to grant editing permissions, you can let them view the design without any risk of changes. Sometimes, you need a junior teammate to edit the copy without altering your design.

Bettina Specht: There is always a gray zone there, right? You can lock things down completely. That is the one extreme. You can give people all the design flexibility they need if you have a skilled team.

But you can also do a lot in the middle, where you want to give folks some prebuilt content rows they can use as a starting point. So, build that design system and your permissions in a way that works for your team.

We believe that combining a strong email design system with thoughtful permissions can help you avoid mistakes even when your team grows, is decentralized, and has many people involved.

Matt Helbig: We also created this Really Good Email Design Checklist PDF with Campaign Monitor, which can help you start your pre-send checklist.

Mary Shoemaker: If you've sent an oops email, which we've all done, this is how to turn your slip-up into a strategic win while staying cool, calm, and collected.

Emily Santos: So this is a question for the chat: When you made an email, did you apologize for mistakes? Should you always apologize when there's a mistake?

Mary Shoemaker: There are mixed responses. It depends on the situation.

Let's discuss when you should send an "oops" email. Not every mistake can be addressed lightly. For instance, a lighthearted email is inappropriate if you lose millions of dollars or leak sensitive customer data. In such cases, you'll likely involve higher-ups.

When sending an apology email, consider the severity of the mistake and the tone of your brand. Some helpful resources are also available, such as a decision framework from Litmus that guides you step-by-step in making that determination.

Matt Helbig: Let's ease up on sending fake mistake emails. While one instance can be fun, sending two may come across as a marketing tactic, and people will eventually catch on. We don't recommend this strategy. I wouldn't advise this approach, as it's not the best long-term strategy.

Mary Shoemaker: Yeah. We all see right through those, right? At least those of us in this group do see right through it. It doesn't feel authentic.

Here's how to handle a mistake effectively.

First, offer a sincere apology—make sure it feels genuine, but don't overdo it. An overly elaborate apology can amplify the mistake, making it seem more significant than it is. Simple emails tend to work better. One survey found that 8% of brands experienced a more positive customer attitude when they included an apology in their emails. So, say something like, "I'm sorry" or "We're sorry we messed up." Just own it.

Next, ensure your message aligns with your brand's identity. As mentioned, your tone should match your brand's personality. If your brand is fun and playful, keep the tone lighthearted. If it's more formal, aim for a professional yet warm approach. Speak in a way that reflects your brand.

Finally, provide a solution and, if possible, a little extra incentive. That same survey indicated that emails containing an apology and a discount saw a 120% increase in purchases. That's significant, so take advantage of that opportunity if you can!

Matt Helbig: I've clicked on more apology emails than original campaign emails because I'm curious about what people apologize for. Situations like website slowdowns, cart issues, or sold-out products can be opportunities to send follow-up emails, such as offering a discount: "We know this sold out faster than we expected. Here's a discount for the next one."

Mary Shoemaker: If the mistake was minor and aligns with your brand's voice, consider incorporating humor to make your communication more engaging. When signing off, infuse your message with warmth and gratitude. A personal sign-off emphasizes that real people are behind the brand, helping to build empathy with your audience. Express appreciation and convey a sense of personality.

So, why does this approach work? It feels personal. Acknowledging a mistake makes your brand appear more human because everyone makes errors. It also sparks curiosity; customers who might have overlooked your first email will likely open the follow-up to understand what went wrong.

Addressing the error builds trust. Not ignoring the mistake, you reassure customers that you care about their experience. Additionally, the follow-up email often has a higher open rate than the original campaign, which boosts engagement.

If you're not familiar with the term, there's a brilliant German word that captures the joy people feel when witnessing others' mistakes. It's true: seeing others mess up can bring a little joy, which makes an "oops" email hard to resist.

Bettina Specht: It's important to inform your customers, customer service, and support team. Remember that the impact extends beyond just your customers; it also affects your team.

Mary Shoemaker: Absolutely. Everybody needs to be involved in the response. If you make a mistake, apologize sincerely, which will engage your audience and build your trust. Then, hopefully, it's smooth sailing.

Matt Helbig: We're all human; mistakes are part of life. What matters is how you recover from the mistake and what steps you take to avoid it in the future. That's the best course of action you can take.

Emily Santos: Thank you for the presentation, Mary Betina, and Matt. I'm going to the question box and selecting the ones that have been most upvoted.

How can we check the HTML file size?

Bettina Specht: Some ESPs have built this feature. If you can export your HTML, you can check the file's details on your laptop. Inspecting the file will allow you to see its size, which provides a good starting point.

Emily Santos: Do you have any advice for testing and queuing complex, dynamic content? We have to test and email dozens of times with different contacts to account for all the dynamic content.

Mary Shoemaker: Yeah, that's tricky. In my experience, you have to test every email. I feel better if I test, see, and review it. It takes a lot longer, but if you're sending out important messaging, I don't know that there are any shortcuts.

Matt Helbig: As you've mentioned, it can get complicated. I've tested 50 versions of an email before, which requires reviewing the various files. I suggest creating a testing document that outlines the different dynamic sections in a spreadsheet to check for each email. This way, you can review the list and ensure the data is being pulled in correctly.

Emily Santos: Are the image size recommendations for each image or the whole collection? The presentation mentioned that all your images should be under 500 kilobytes.

Bettina Specht: Larger images and many images can increase loading times, especially on mobile devices, where data use is a concern. It's best to keep individual image sizes below 500 kilobytes and GIFs ideally under one megabyte. Additionally, maintain a good balance between images and text in your emails to avoid overwhelming your recipients.

Matt Helbig: Sometimes your ESP may even reject you uploading huge images. You don't want to drop in a 5,000px image if it's like a 600px-wide email.

Emily Santos: Any AI tools to help with the QA process?

Mary Shoemaker: Yeah, that's a good question. I don't trust AI enough yet to catch everything. I'm sure it's coming, and maybe there are some good tools out there, but that makes me nervous.

Bettina Specht: We've been experimenting with some features on the Beefree side, particularly regarding our alt text capabilities.

One important aspect we focus on is helping users automatically populate alt text using the power of AI. Many people overlook this, but it's crucial for accessibility. We've been developing tools to assist users in catching any missing alt text, and AI can even generate ALT text for you, eliminating the need for manual input.

Emily Santos: Bettina, how do Smart Check and Beefree differ from our AI solution? Smart Check is entirely different and not AI-powered.

Bettina Specht: I always think of Smart Check as a tool for examining the hard facts.

If we check whether certain elements exist in the code, we can determine that by analyzing the code itself. There's no need for AI for this assessment; we can look at file sizes and image dimensions. So, we verify some of these hard facts, which are not related to AI.

Emily Santos: Do you have advice on responding to a stakeholder's question, "How could you possibly have missed that?"

Matt Helbig: Defining roles and responsibilities is crucial. Involve stakeholders in the process to ensure they're comfortable approving decisions. Create a paper trail to document changes and check-ins. This can help analyze mistakes and identify where processes may have failed to prevent future failures. That way, it's not "How did you miss this?" It's "How did we miss this?". It may be time for a team therapy session.

Mary Shoemaker: Yeah, I would agree with that. I always say to come back to them with results. This is what happened, and this is why it won't happen again.

You're more of a team than just individuals. Consider the team you're on if they're making you feel that way about a simple human mistake. We all make mistakes; it's going to happen.

Bettina Specht: Someone mentioned in the chat that capacity might be an issue and that you could feel overwhelmed while juggling many campaigns simultaneously with a tiny team.

If you're experiencing this and believe the current setup will not lead to mistakes, it's worth having another conversation with your boss. Consider discussing potential changes that could help alleviate the pressure.

Emily Santos: What is the easiest way to proof dark mode? Is there a tool for that?

Bettina Specht: The challenge with dark mode is that there isn't just one type; different email clients each have their version of dark mode. This adds a layer of complexity to an already intricate situation. Tools like Inbox Monster and Litmus are excellent options for previewing your email in dark mode across various clients, including Gmail.

If you're using Beefree, we also provide dark mode previews, although not for every inbox.

Emily Santos: Thanks to all who attended and contributed to our first webinar of the year! Special thanks to our guest Mary Shoemaker, resident speakers Betina and Matt, and our moderators! ✌️