Hold Up is a game mechanic in Persona 5. It allows you choose between an All-Out Attack or a Special conversation by having the protagonist and the Phantom Thieves of Hearts surround the Demons and point their guns at them.
To initiate a Hold Up, you must Down all foes by targeting their weaknesses or by critically hitting them. A Hold Up is automatically initiated, from which you have the following options;
Similar to previous Persona games, this is the same special attack that can be initiated when all enemies are downed. Choosing this option cause the current non-Downed teammates in battle to join the protagonist in a team attack that deals massive damage to the enemies. As a bonus, should this attack kill all enemies, a special conclusion screen appears called a Finishing Touch where a party member is highlighted with a special background and dialogue. The character selected depends on which character scored the final downing hit.
For example, if Morgana downs the last enemy, he will be highlighted, even if he did not down all of the other enemies himself.
The protagonist can demand that the shadow give him some money in exchange for their freedom. The money depends on the enemy's level, but is higher than defeating the Shadow itself. They can also request an item as well, which is fixed. Should the player choose these options, all other enemies during the Hold Up also leave, but they do not give any extra Money or items if they were not defeated. Players are also given the ability to request even more gold after their initial negotiation, allowing their profits to double. However, there is a chance for this to fail, causing the shadow to attack the player and end the negotiation. If the player downs the enemies again.
Boosting the Toranosuke Yoshida social link also gives you the chance of acquiring even more money or a rarer item from the Shadow. Also, having the same Persona in their party as the one they are negotiating with, they will acquire even more gold as well.
The protagonist can request that the Shadow join him as a Persona. Doing so requires that he appeal to them by answering two questions. All Shadows have an personality attributed to them, which can be viewed by Analyzing them or viewing their pre-negotiation blurb when downed. A Shadow can either be Timid, Irritable, Upbeat, or Gloomy, each requiring that the protagonist to answer their questions with a certain tone. Timid Shadows prefer Kind answers, are neutral to Serious answers, and dislike Playful/Ambiguous answers. Irritable Shadows prefer Serious answers, are neutral to Playful answers, and dislikes Kind/Ambiguous answers. Gloomy Shadows prefer Ambiguous answers, are neutral to Kind answers, and dislike Serious/Playful answers. Upbeat Shadows like Playful answers, are neutral to Ambiguous answer, and dislike Serious/Playful answers.
If the Shadow likes their answer, a yellow musical note appears. If they are okay with the answer, they will have blue sweat drops. If they dislike the answer, they will have red anger marks. They player either needs to answer their second question with a positive response to acquire them as a Persona, even if they get a disliked response on the first one. If the player answers their second question with a neutral answer or if the player level is lower than the Shadow, they will give him an item. If the second question is answered with a disliked response, the Shadow will attack them, causing the negotiation to fail.
If the player gives a Shadow an unfavorable response, and if a teammate has at least a Rank 4 in their Confidant with the protagonist (6 for Goro Akechi), they have a chance of stepping in and helping the protagonist retry at negotiating. Additionally, if the player has already acquired that Shadow's mask, they will join for free without needing to negotiate once more.