Spell-checkers have come a long way since a West Coast beach boy with an FBI record invented the first prototype at MIT in the 1960s. Nowadays, the technology is not only ubiquitous in all word processors, quietly creating more error-free writing around the world, it also exists online, where it can point out mistakes in real time while we write emails or post on social media.

But while spell-checkers’ ability to catch slipups and understand context has evolved tremendously, most of these programs still struggle to identify homophones, those pesky words that sound the same but carry different meanings and, often, different spellings.

Ensure/Insure
It seems strange that in order to ensure my son can receive medical treatment, I need to insure him with the healthcare company on the day of his birth.

Every day/Everyday
Just because the office attire is everyday wear doesn’t mean you should wear the same clothes every day.

Formerly/Formally
Formerly a Buddhist monk clothed only in a tunic, he was confused by the need to dress formally, in a shirt and tie, for work.

Guerilla/Gorilla
The paramilitary forces had a new tactic; they were going to use actual gorillas as foot soldiers in their guerilla warfare.

Led/Lead,
He led them through the dangerous forest of giant spiders with only a headlamp and a lead pipe. As the lead scout, he needed to be brave and fearless even though he felt incredibly frightened.

One/Won
She won the costumed thumb war competition by one measly point.

Pedal/Peddle
If you want to peddle stolen goods to innocent people, you’d better be prepared to pedal your bike as fast as you can away from the town when you’re done.

Pore/Pour
If you pore over your schoolbooks with the same discipline that you apply to gaming, I won’t be forced to pour this macaroni over your head.

Premier/Premiere
The premier of Switzerland eagerly awaited the premiere of the new production of the Sound of Music. The woman cast as Maria was the country’s premier actress.

Principle/Principal
School principals should be people of principle. Their behavior and attitude should, in principle, be an example to all students.

Reign/Rein
Take the reins and lead the horse as if you’re ruling a kingdom and your reign has lasted five decades.

Weather/Whether
Who cares about the weather? We’re going to have a good time regardless of whether it’s raining, snowing, or glowing.


Credit: Grammerly

Interesting.
What about "In other" and "In order"