How to Not Send an Embarrassing Email By Mistake

The lightning-fast speed of email, online messaging, and social media helps make life efficient and productive—but it also sets you up for some seriously mortifying mishaps.

how-to-not-send-an-embarassing-email-by-mistakeiStock/brianajacksonReview this email checklist before you hit “send.” These four rules may save you from major regret or an epic office freakout.

1. Read through the reply line
When the inbox becomes flooded with messages, especially when we’re on deadline, it’s natural to respond quickly. However, sometimes hitting “Reply All” accidentally can change the course of your day in minutes. It’s always important to read your email and scan all names listed on the thread before releasing a message into cyberspace. This includes Tos, CCs, and the hidden BCCs. Make sure you’re aware of all subjects receiving the message to eliminate any surprises.

2. Create a rough draft
Sometimes the cleverest people are also the worst spellers. If this includes you, don’t underestimate the value of spellcheck software or grammar apps on your computer. It’s much easier to proofread your work and correct errors before actively exchanging emails than drafting another message apologizing for your goof.

3. Don’t get caught in the drama
Sometimes we can think more clearly when we write down our feelings, but when an email exchange with your name attached is at risk of being read by the wrong person or interpreted incorrectly, it might be time to step away from the keyboard and go have a live conversation. If you have a problem with a coworker, client, or friend, address the issue with the subject directly instead of starting an email chain that could escalate hostilities. (Avoid these annoying email habits while you’re at it.)

4. Use settings as protection
If you ignored the first three rules, this piece of advice could bail you out. If your fingers worked quicker than your brain, there are some setting adjustments to help you delay or delete a message, but you are up against the clock. “Because emails get delivered by copying your message to your recipient’s server, deleting anything on your end doesn’t really solve the problem,” according to the site Lifehacker. “Once the copy gets to them, there is very little you can do.” Here’s a way around that: If you use Gmail, set a time delay that will allow you to undo a message as needed. Go to your Gmail settings, then to the Labs section, and enable “Undo Send.”

Popular Videos

Originally Published in Reader's Digest

Hope Daniels
Hope Daniels is a contributor to's Lifestyle section, where she writes about life’s gifts and slips. From the depths of personal routine habits to a hilarious look at social blunders her articles have also appeared on partner sites, the, family and Her work in parenting and pop-culture has also been published on and ScaryMommy. She earned her BA in Journalism from Indiana University.