At one time or another, everyone has sent an email that couldn’t be taken back. Whether it was an unintended company-wide email broadcasting personal business or a simple spelling error in an important communication piece, nothing can stop a career in its tracks like a major email mishap.

If your company’s email setup doesn’t allow you to retract an interoffice email, double-checking each message before hitting “send” is a must. Pay particular attention to the “To” field, where some of the most disastrous mistakes occur.

Mistaken Identity

It can easily happen. You’re emailing Bob to complain about Jane and, with Jane still on your mind, you type her name into the “To” field. If Jane is a colleague or subordinate, you’ll simply have years of awkwardness between you. If she’s your boss, you’ve probably lost your chance at that corner office.

Keeping an eye on the “To” field can help protect against mistaken identity. To be extra cautious, however, a better practice might be to avoid putting anything an email you wouldn’t want anyone else to read. Emails have a way of ending up in the wrong hands occasionally.

Accidental Group Emails

The Wall Street Journal referred to it as “the button everyone loves to hate.” Reply to All is a dangerous feature, getting professionals in trouble in a variety of ways. Often senders don’t notice the names of associates or clients in the CC field, leading information to be shared to the wrong parties.

Another group email error happens when one party replies to a distribution list. The next hour is usually filled with a flurry of emails, beginning with, “Why are you emailing me? Who are you?” and eventually escalating to, “Everyone stop hitting reply to all and the flurry of emails will stop!” In some instances, large enterprises have been forced to cut an email exchange off at the server level to stop the deluge.

Email Marketing Fail

As email marketing has evolved, there are a variety of ways a message can go astray. Numerous campaigns have kicked off with an embarrassing spelling or grammar error. At least one company—The New York Times—accidentally sent a discount offer to eight million subscribers, rather than the 300 former subscribers it was intended for, creating a backlash as loyal customers asked why they weren’t getting the same deal. In many instances of email marketing disasters, the company was hasty in its efforts, skipping the crucial step of reviewing emails before they went live.

Many businesses don’t realize email marketing campaigns can be tested just as any other marketing effort is. Through split testing, a campaign can be both strategized and analyzed, using results from the last campaign to inform the next. Emails can also be created and scheduled for a later delivery, allowing multiple team members to offer approvals before they go live.

With so many emails being sent each day, it’s easy for harried professionals to occasionally misfire. A few preemptive measures could save an employee years of repercussions.