Shadow

Ability

On your first night, you learn an in play Agent role. If you were obsessed that you were this role, you gain their ability when they die.

John is the Analyst. The Shadow wakes up on their first night and learns that the Analyst is in play. During the game the Shadow is obsessed that they are the Analyst. John dies, and the Shadow gains the Analyst ability.
Jane is the Assistant. The Shadow wakes up on their first night and learns that the Assistant is in play. During the game the Shadow is not obsessed that they are the Assistant. Jane dies, and the Shadow does not gain the Assistant ability.
The Shadow is only malfunctioning on their first night. Nobody is the Bodyguard. The Shadow wakes up on their first night and incorrectly learns that the Bodyguard is in play. During the game the Shadow is obsessed that they are the Bodyguard. The Shadow never becomes the Bodyguard because nobody was the Bodyguard. If the Shadow stops malfunctioning after their first night they do not gain new information.
The Shadow is malfunctioning. Adam is the Bureaucrat. The Shadow wakes up on their first night and learns that the Bureaucrat is in play. Adam dies, but the Shadow does not gain the Bureaucrat ability because they were malfunctioning when Adam died.

As the Shadow you must decide whether you want to be obsessed about being the role that you learnt or not. If you decide to be obsessed then you will almost certainly attract suspicion when you start claiming the role of another player, but if they die your team will still get to use their ability through you. If you decide not to be obsessed then you can be open about the role that you learnt, this will help to confirm the player that claims to be that role, but your team will not be able to get the benefits of their ability through you.
If you want to gain the ability of the role that you learnt, make sure the Narrator hears you making an effort to convince others that you are that role. Obsession is primarily about trying to make a genuine attempt to convince others of something.

The first night that the Shadow is in play, wake up the Shadow. Tell them an in play Agent role. Send them back to sleep. If the Shadow was obsessed that they were the role they learnt during the game, then when the player who has the role that the Shadow learnt dies, interact with the Shadow in a way in keeping with the ability they have gained: they will wake up when they would wake up, and act when they would act.