Along with James and Meowth, Jessie reappeared in New Places... Familiar Faces!, returning to their original plan of catching Ash's Pikachu. They've also added new Pokémon to their team, with Jessie catching a Frillish sometime before meeting up with Ash and company. However, she is forced to give it and her Woobat away to Giovanni in The Dream Continues! under the pretense that she captured them for him. She also regained Wobbuffet as part of her team in the episode. In A Festival Trade! A Festival Farewell?, Jessie mentions that Pumpkaboo was the only one who remembered her birthday, which happened some time after she caught her. Jessie and James disguised themselves as Officer Jenny and Nurse Joy, respectively, while attempting to steal the Moltres Flame where a crowd of real Jennies and Joys are appearing. Interestingly, unlike when Jessie disguised as Nurse Joy previously, James does not use a mask, but their disguises for the most part appear flawless, except for their true eyes obviously being shaped differently from the real Joys and Jennies, and also because of James's blatantly fake falsetto voice. Jessie and James appeared in kimonos, with Jessie holding a goldfish in a bag while James had sweet treats in his hands. In this game, Jessie, from the alternate movie continuity, somehow got transported to Pasio while chasing a Shiny Celebi. Unlike most characters in Pokémon Masters EX, Jessie's appearance is based directly on her anime incarnation, and retains her Japanese and English voice actors.

Jessie wore a red dress for the Saffron City Contest. She wore this outfit again for the Chrysanthemum Island Contest in Spontaneous Combusken! and the Mulberry City Contest in New Plot, Odd Lot! Jessie is very close with Arbok as she has known it since it was an Ekans. Also, Jessie would do anything to protect Arbok and it would do the same for her. However, Jessie released Arbok to be with its own kind. Despite being apart, Jessie knows her relationship with Arbok will always be with her. Jessie, James, and Meowth disguised themselves as Nurse Joy, Raoul Contesta, and Mr. Sukizo, respectively, and volunteered to judge the Contest Battle between May and Drew. However, their cover was blown by Harley and his Cacturne. The trio's main mission is to steal or obtain Pokémon for Giovanni but their personal goal is to capture Ash's Pikachu. Due to this goal and a lot of coincidences, they are able to tail Ash on his journey, occasionally sending reports to their boss about rare or powerful Pokémon they discover or research that would turn a profit. In the Movie Pokémon The Movie 2000: The Power of One, Jessie's age was said to be 25 in the Japanese cut. This was, however, missing in the English dub. This age of hers is not confirmed either as, in the anime, her age has been mentioned several times, almost all of them being different.

In Pokémon the Series: Sword & Shield, Jessie's appearance remains unchanged and her magenta hair appears in a glossy style. These costumes were used again in Stealing the Conversation!, where the trio posed as Jubilife TV reporters wanting to interview Dawn. James posed as a proud father in the audience as Jessie, going by the pseudonym "Jessilynlyn", and Meowth competed in the Pokémon Ping Pong Tournament.

Jessie and James wore electric-proof suits, complete with a blue helmet with protective visors and gloves. While their armor worked, they forgot to protect their balloon and were sent blasting off. Elena Ramírez ( EP159- EP167, EP169, EP192- EP205, EP230- EP233, EP274- AG017, AG033- AG034, AG093- AG100, one scene of AG133) Jessie and James posed as auxiliary ladies from the Pokémon Battler's Association, though Wobbuffet's unannounced appearance helped Ash and his friends see through the disguises. In DP 171 Jessie lost in the contest. Princess Salvia, disguised as Dawn, gave her the ribbon for the performance she gave during their battle in the Final round.

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The trio disguised themselves as Ancient Pokémon experts. They fooled Dr. Kenzo, who took them on a guided tour through the Oreburgh Mining Museum. Jessie returned once again in Pokémon the Series: XY, following Ash to the Kalos region. In Kalos, Jessie became a Pokémon Performer, competing under the aliases Jessilee and Jessilia (Japanese: ムサヴィ Musavie). In the Japanese version of The Power of One, Jessie tells Ash and Misty, who are 10 years old, that they're 10 years too young to talk about love, and James adds that he and Jessie are five years older than that, placing them both at 25 years old.

In The Battlefield of Truth and Love!, Jessie and Wobbuffet battled James and his Mareanie. Fully confident in her own victory, she allowed Wobbuffet to act however he pleased, which he did by repeatedly using Counter and Mirror Coat against Mareanie's Spike Cannon and Sludge Bomb. However, Mareanie ultimately managed to defeat Wobbuffet with a relentless Spike Cannon barrage after James gained a newfound resolve to win, thus eliminating Jessie from the competition. Jessie and James disguised themselves as inventors with a "machine" that supposedly makes the user's Pokémon stronger, but instead, winds up as empty Poké Balls. Jessie is prone to vanity and explosive anger. She values her appearance, and she can get furious when her face or hair is damaged, such as in The Tower of Terror, Tracey Gets Bugged, Don't Touch That 'dile!, A Tail with a Twist, Maxxed Out!, A Meteoric Rise to Excellence!, One for the Goomy!, and Good Friends, Great Training!. When this happens, she may do things like beat up a Pokémon such as Meowth or her Seviper. Furthermore, Jessie goes into a violent outrage whenever someone insults her beauty by calling her old, such as in the episode The Battling Eevee Brothers when Misty calls Jessie an "old hag" (Japanese: oba-san). She shares this trait with James, who hates being referred to as an old man. She is also angered (compared to her companions, who are usually depressed when they fail at something) when missions are either failed or botched, which is a regular thing. At times, her anger is also shown to scare James and Meowth, usually when they are expecting it or if she really loses her temper. This intense anger was demonstrated in the Indigo League, Orange Islands, and part of the Johto League story arcs. However, her anger tantrums have become less frequent and eruptive over the next story arcs. In Luxray Vision!, the group reused these guard outfits to remain undetected while they stole an Old Charm. While establishing the unofficial Powerzone Gym, Jessie posed as the Gym Leader "Princess Powerzone", and wore a dress and glasses with remarkable likeness to her Seviper. James dressed up in a white suit with a pink shirt and matching pink tie and orange shades. Meowth wore a red suit with a blue bow tie and regular shades.

Jessie and James posed as members of a congratulatory committee in an attempt to steal the Rustboro City Coordinators' Pokémon.

Jessie, Meowth, and Wobbuffet posed as employees from the Pokémon Au Pair service. However, James, who was still upset from leaving his Cacnea with Gardenia in the previous episode, spoiled the scam. The trio wore trench-coats, hats, and dark glasses to remain undercover while they took a train between Snowpoint City and Lake Acuity. The trio are requested by Looker to stop Team Plasma and they steal Team Plasma's Pokémon using Yamask and Woobat. After Team Plasma is defeated they return to their mission of capturing Pikachu, but always fail. There is no official confirmation about the rank vs uniform colour meaning but it's speculated that White uniform is for B-Rank agents. Jessie bears a striking resemblance to Jessebelle and James' mother. This fact was commented on in "Holy Matrimony!"This might have been caused by the change in medium when the series switched from hand-drawn to digital animation. In Party Dancecapades!, Jessie and her team members decided to attend a dance party hosted by Monsieur Pierre. After seeing Serena and her friends go inside, Meowth noted that it would be a perfect chance to catch Pikachu. Jessie, however, decided to let go of these plans in favor of attending the dance party and decided on James being her date while Gourgeist decided Inkay to be hers. Later, she was seen flailing James during their dance. With the dance party over, Monsieur Pierre announced a Tag Battle and Miette and James were partnered against Ash and Serena. Despite James's chagrin, Jessie sternly told him to win the battle but he lost, leading to her and her Gourgeist eating from the table behind them out of frustration. The trio posed as Team Electabuzz fans to convince Casey, an avid Electabuzz fan, to have a rematch against Ash while they plot to snatch Pikachu. Jessie was disguised as a lady who has lost her Piplup, while James and Meowth were disguised as gentlemen. In The Ultimate Test, Jessie decided to take the Pokémon League Admissions Exam to see if she could enter the Indigo Plateau Conference and add that achievement to her résumé. However, during the theory test, she rose from her seat and started to argue with the instructor, which led to her being expelled.