In Pokémon the Series: Sword & Shield, Jessie's appearance remains unchanged and her magenta hair appears in a glossy style. A running gag of the series is that Jessie is almost always the male when she and James disguise themselves as a couple. Jessie then became eligible to participate in the Sinnoh Grand Festival, and she made it into the semi-finals, but lost to Dawn. She also participated in the Pokémon Summer Camp and got a diploma/credit for having studied (she was disguised as Jessilina). After the Sinnoh Grand Festival, Jessie abandoned the Jessilina alias. She is based on a combination of Takeshi Shudō's old girlfriend from when he was in school, and Majo, the female antagonist of the Time Bokan anime series. In Master Class Is in Session!, having gained the two Princess Keys needed to enter the Master Class, she entered the Gloire City Pokémon Showcase Master Class. In the first round, she performed against Nini and Concetta, where she dazzled the audience with Shadow Ball from her Gourgeist. When the second part of the first round began, she chose to strike a series of poses with her Gourgeist while Nini and Concetta appealed to the audience, but later joined the appeals, commanding Shadow Ball from her Gourgeist which enveloped the stage in a lilac smoke. Due to her appeals, she managed to advance to the next round in which she participated with Meowth, and made it through to the top three semi-finalists. Jessilee seemed pleased when Monsieur Pierre announced the rules for the semi-final round in the next episode, claiming she just has to do what she has been since doing. Despite putting up a good performance with Meowth and her Gourgeist, she was defeated, and despite her partners' fear, did not seem sad about it, instead being happy that Kalos could see her beauty. When the Master Class was over, she was seen walking through Gloire City rather silently, causing James, Meowth, Inkay and her Pokémon to worry and fear her wrath. However, she shrugged their fears and decided that she just wanted to give a feast to them, which shall be financed by James, for supporting her.

Jessie becomes less selfish and less harsh towards her teammates: James & Meowth as the series progresses. In 'Pokémon Journeys,' it is demonstrated several times that Jessie is a coach of 'self-confidence' for her teammates. As a child, she also had a doll that she adored, but was taken away by a Jynx to be repaired by Santa. She thought that Santa was actually a Jynx and that Santa (Jynx) stole her doll. At the end of the episode, the trio decided to capture Santa for Jessie's gifts, but instead, a Jynx came to their window and used Sweet Kiss, causing them to fall into a deep sleep. During the Lumiose Conference, he along with Jessie, Meowth, and Wobbuffet serve as cameramen for one of the members of Elite Four and news reporter, Malva, and are unaware of Malva's alignment with Team Flare. But as Lysandre causes chaos through Lumiose City with Z-2 as Zygarde in its 50% form, James, Jessie, and Meowth had no choice but to help Professor Sycamore, Mairin, and Serena. With the assistance of the Hoenn Champion, Steven Stone, the trio finally remove their disguises and tells them to move on to get Chespie while facing off against Team Flare grunts including Celosia and Mable. She also values her beauty and long hair; she will become furious if her face or her hair is damaged. A prime example is in Tracey Gets Bugged when a younger Scyther manages to slash her hair down to a shoulder-length, devastating her and sending her into a rage. Jessie also shows her violent outrage when someone insults her beauty by calling her old. Her anger also scares James and Meowth, especially when their missions end up in a failure. 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 seems to have a special preference for snake-like Pokémon, owning both an Arbok and a Seviper. In The Ninja-Poké Showdown, she expressed a preference for Poison-type Pokémon in general, though several Bug-type and Ghost-type Pokémon have since appeared on her team including Yanmega, Gourgeist, and Mimikyu.

In DP 102 while Ash was fighting Fantina, Jessie is seen participating in a Pokémon Contest in which she won with her Yanmega. After the disaster, she and her teammates claimed sole credit for defeating Team Flare to Giovanni. Jessie and Meowth are also disappointed when James successfully catches Inkay by luring it in with food. Therefore, when she tripped into a wild Pumpkaboo, she decided to capture it.Although she is shown to be very mean to her own Pokémon such as punching or shouting rudely at them, she does care for them. For example, she along with James and Meowth helped Arbok to escape with Weezing, and a group of Koffing and the Ekans, by taking hits from Rico's Pokémon. She also let Dustox follow her true love by smashing Dustox's Poké Ball. 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). Tempest. The plan continued in All for the Love of Meloetta!, where they were able to injure Meloetta before it was found by Ash and Cynthia. In Meloetta and the Undersea Temple!, the operation began in full, with the trio capturing Ash, Pikachu, and Meloetta and bringing them to the Abyssal Ruins.