Eugene sets out to find a role for himself in the castle and decides to be a royal guard. The Captain of the Guard, however, isn't so eager to have a former crook and rulebreaker under his command. Meanwhile, a famous artist comes to paint Rapunzel's portrait at the castle.
Tropes in this episode include:
- Book Dumb: Apparently, Eugene only went to school for three days and as such, he's woefully terrible at math.
- Boot Camp Episode: This episode deals with Eugene attempting to join the Corona Royal Guard, complete with the Captain as the Drill Sergeant Nasty and lots of Training from Hell.
- Both Sides Have a Point:
- The Captain believes in a regiment that can follow orders, obey rules and show discipline. For this reason he doesn't trust Eugene, who hates following orders and rules. Eugene realizes that the Captain has a point when a crossbow's safety catch saves his life. He preemptively turns down what he thinks is the Captain offering his job back.
- Eugene is also right in that criminals won't wait for guards to follow rules and catch them. He's good at thinking outside the box. The Captain realizes this when the real artist coming to do Rapunzel's portrait shows up, Bound and Gagged, which proves Eugene's theory.
- The Captain also gets a point (in a jerk-is-right sense) when he fires Eugene for not only neglecting to do his job, but neglecting to do it in the correct time stamp.
- Boxed Crook: Eventually, this becomes Eugene's new role in the castle. The Captain doesn't want him as a guard, and Eugene decides he doesn't want to work for the Captain. Eugene decides to instruct the royal guard in how criminals act and behave.
- Call-Back:
- Cassandra's dad doesn't want to hire Eugene because the latter is a rulebreaker and humiliated him badly during the quest to get the crown.
- Eugene mentioned in the Tangled film that crime went down overnight after the Lost Princess was found. We see him offering his services as a former criminal to help the Royal Guard catch thieves.
- Many of Rapunzel's talents and hobbies that appeared in "When Will My Life Begin?" from the first movie are referenced here, with everything she considers having in her portrait.
- Character Title: The episode is named "Fitzherbert P.I.", after Eugene.
- Defrosting Ice Queen: Cassandra becomes nicer to Eugene on seeing him make a genuine effort to become a guard. She realizes that he really wants to turn his life around, and isn't just a Gold Digger who wants to sink his claws into Princess Rapunzel.
- Desperately Looking for a Purpose in Life: Now that he's no longer a criminal, Eugene decides to figure out what he wants to do. He definitely wants to be more than Rapunzel's "almost-fiancee", but it seems his criminal skills keep him from getting a real job, and he can't just be in the castle as a stray from the gutter.
- Dirty Coward: Shorty more or less indicates he would willingly abandon women and children to a thief for money.
- Distinction Without a Difference: Big-Nose doesn't want to say that he agrees with Cassandra that Eugene's not good at anything but being a criminal, but he has independently come to the same conclusion. Then again, he may have been trying to placate Eugene because he and everyone doesn't so much care about Eugene's personal problems.
- Drill Sergeant Nasty: We see the Captain of the Guard in action as the drill instructor. However, he has a special nastiness reserved for Eugene, AKA Flynn Rider.
- Everyone Has Standards: Even though Eugene says Cassandra would be thrilled if he failed the guard training, she actually is disappointed that her father is breaking the rules to make sure Flynn Rider doesn't earn the uniform.
- Exact Words: The objective of the final obstacle course was to make it through until the whistle blows, which the Captain times with an hourglass. Just when he's about to cross the finish line, Eugene goes back to claim Shorty, coming in slightly late. The Captain brags, until Eugene blows the whistle after he and the other trainees have crossed the line. The Captain never mentioned that they had to beat the hourglass, or that he had to be the one to blow the whistle.
- Extra Digits: Corona's former King Robin the Eleventh is called that for having eleven fingers. When a thief steals his portrait and leaves a fake one, the switch is noticed because King Robin is portrayed as having only ten digits in the fake one.
- Failure Montage: Eugene's job search has him fail bakery because of Oven Logic, fail at a taxi service because he rushes to the wrong destination, and in a twist succeed at being a cobbler but get fired because he robbed his boss in the past.
- Foreshadowing: Eugene fails bakery because of Oven Logic and it foreshadows how he eventually loses a later job as a palace guard. As per his dungeon duty, he's supposed to make one round every five minutes. When he makes two rounds in a row to have a ten-minute-break, the dungeon inmate under his watch takes advantage of this to escape. Apparently, math was the real enemy.
- Gratuitous Italian: A plot point. The impersonator painter uses this when coming to the palace, but Eugene catches on because the Italian is "atrocious". The actual painter speaks fluent English, and his accent is lighter.
- Hidden Depths:
- Eugene speaks fluent Italian. That's when he gets suspicious of the impersonator painter who messes up his subject-verb tense. The Captain is surprised upon hearing this.
- Queen Arianna's royal portrait indicates she has many talents and interests, even if so in a clumsy way.
- I Don't Pay You to Think: Captain directly tells Eugene this after he's given dungeon duty and he questions the assignment.
- King Bob the Nth: Subverted. Robin XI is known as such because he had eleven fingers.
- Let Us Never Speak of This Again: A variant; when each realizes that the other has a point, the Captain and Eugene tell the person or horse nearest to them to never mention it.
- Literal-Minded: Feldspar the Cobbler's response after he finds out Eugene was the one who stole a crate of his boots in the past:Eugene: Does this mean I'm getting the boot?
Feldspar: No! It means you're getting fired! - The Load: Shorty does nothing except follow Eugene around like some sort of human dog, thinking the boot camp was the men's room, not pay attention to what's going on, and gets pushed in the water.
- Moving the Goalposts: Eugene lampshades that the Captain is doing this with regards to his training. Cassandra tells Eugene to outwit her father at doing it. When Eugene does succeed, the Captain decides to assign him to dungeon duty—which is one of the thankless jobs.
- Not With the Safety On, You Won't: As part of crossbow wielding procedure, the safety must always be on. This is what saves Eugene when he got cornered by the art crook who stole the crossbow. But after Eugene takes it back, his finger slipped and the dart went off.
- Old Shame: Queen Arianna's opinion of her royal portrait. Unlike all the other portraits, she has hers covered in a tarp and shoved into a dark forgotten room of the castle.
- Oven Logic: Eugene reasons that if a pie bakes in one hour at 300 degrees, then 600 degrees will do the same in half the time. Cue burnt pie.
- Pet the Dog: Cassandra tells Eugene that as a rulebreaker he knows how to outwit someone breaking the rules. She also believes him when he realizes that the "painter" that came to do Rapunzel's painting was an impostor.
- Police Are Useless: It's shown the guards suffer from this problem because they use predictable tactics which allow criminals to slip by easily. The Captain of The Guard attempts to correct this problem by having Eugene enlighten others on how to think like a thief to catch one.
- Reassigned to Antarctica: The Captain gives Eugene dungeon duty because it's grim task that is so idiot-proof and isn't convinced that a former criminal has what it takes to be a part of Corona's elite.
- Rule of Three: Eugene's first attempt at a job has him take an old lady home, but it's the wrong house. The second attempt has Eugene bake a pie, but he followed Oven Logic. In the third job, Eugene is actually successful at it, but he gets fired because he robbed the guy a year prior.
- Screw the Rules, I Make Them!: The captain can make and break the rules simply because he can, and does so to make sure Eugene washes out and doesn't make it. However, Eugene decides to beat the captain at his own game.
- Shout-Out: A subtle one to Sofia the First. The first job Eugene attempts is being a baker's assistant. King Roland the Second temporarily became a baker in "The Baker King". One of the other jobs he tries his hand at is being a cobbler. That used to be Queen Miranda's job before she married King Roland.
- Stylistic Suck: The impersonator does a terrible portrait of Rapunzel. Even Eugene can't find anything nice to say about it. This clues him in that the painter isn't the real one.
- Training from Hell: Naturally, the Royal Guard are Corona's elite, so this is to be expected, but the Captain really had it out for Eugene with the training he put him through.
- Xanatos Gambit: The Captain's plan for Eugene to prevent him from becoming a Royal Guard: The captain can sabotage his training, and if Eugene washes out, he doesn't make it. If Eugene passes, then he gets an undesirable, yet idiot-proof assignment so that he can't possibly be a liability to the guard. It's a win-win for the Captain.
