Post War Dreams

Missable

You can do this before or after Helping Kara and Nolan the Gatekeeper.

From the first small roof that you jumped on (right after the initial stop stop, where the path splits up/down), climb up onto the ledge and take the path up. Ignore the ladder you come to and just keep running right. Jeffrey will be at the very end. Speak with him (choose "Curious" or "Threaten", then "I'll help") and exhaust the conversation. The trophy will unlock shortly after the conversation has ended.

You do not need to complete the quest he gives you.