Pterodactyl Hybrid (Disney)

IDW comics
A sheet of paper showing Iron Will appears on My Little Pony: Friendship is Magic Issue #1 page 3/Dynamic Forces cover RE. Iron Will appears alongside several other creatures on cover RI of My Little Pony: Friends Forever Issue #4. In My Little Pony: Friendship is Magic Issue #19, an alternate universe Iron Will is referred to as "Mayor Iron Will?" on a sheet of paper. In My Little Pony: Friends Forever Issue #10, Fluttershy helps Iron Will get in touch with his "inner pony" so he may better support his wife and son.

In Siege of the Crystal Empire, Iron Will takes part in an invasion of the Crystal Empire with Flim and Flam, Lightning Dust, and Queen Chrysalis in hopes of regaining his lost charisma. Iron Will's participation in the invasion is voluntary at first, but by Friendship is Magic Issue #36, he begins to have second thoughts in consideration of his family.

My Little Pony (mobile game)
Iron Will is a character in Gameloft's mobile game. His in-game description states, "IRON WILL IS 200% CONFIDENT THAT THIS DESCRIPTION CAPTURES IRON WILL'S UNIQUE BRAND OF ASSERTIVENESS!!!"

Merchandise
Iron Will appears on the Chaos is Magic and Season 2 posters.

Quotes

 * "That's no joke, friends. Iron Will is so confident that you will be 100% satisfied with Iron Will's assertiveness techniques, that if you are not 100% satisfied, you. Pay. Nothing. But I pity the foal who doubts Iron Will's methods."
 * — Putting Your Hoof Down


 * "Iron Will's my name, trainin' ponies is my game."
 * — Putting Your Hoof Down


 * "You were nothing but a doormat and Iron Will turned you into a lean, mean assertive machine!"
 * — Putting Your Hoof Down


 * "Iron Will's Cruise of the Princesses makes no guarantees as to the participation of actual princesses. But Iron Will learned his lesson before. Satisfaction not guaranteed. No refuuuuuuunds!"
 * — Once Upon a Zeppelin


 * "They call it "making friends", because you have to make creatures be your friends!"
 * — A Matter of Principals


 * "You're right! I did say me! Now I said I! Iron Will is losing it!"
 * — To Bertha, My Little Pony: Friendship is Magic Issue #34


 * "Iron Will is ready to bring the pain!"
 * — My Little Pony: Friendship is Magic Issue #35


 * "Iron Will is scared of nothing! But Iron Will has a family! He didn't want to overthrow the kingdom!"
 * — My Little Pony: Friendship is Magic Issue #36

List of Iron Will's assertive sayings in chronological order:
 * "Don't be shy, look 'em in the eye."
 * "When somepony tries to block, show them that you rock!"
 * "Don't be sorry! Be assertive!"
 * "Never apologize, when you can criticize."
 * "Attack the day."
 * "Treat me like a pushover, and you'll get the once over."
 * "Maybes are for babies!"
 * "You laugh at me, I wrath at you!"
 * "Cut in line, I'll take what's mine!"
 * "You apologize, I penalize!"
 * "You make me lose, I blow my fuse!"
 * "If you laugh in my face, then it's time to erase!"
 * "Put food on my head, consider yourself d—"
 * "If you're quiet, I don't buy it!"