Fallout 4 created by Bethesda Game Studios.
Images used for educational purposes only.

Prerequisites: Complete Mercer Safehouse
Trigger: Speak to P.A.M.
Reward: 300 Bottlecaps, Covert Sweater Vest, 300 XP

You’ll receive Jackpot from P.A.M. immediately after completing Mercer Safehouse and speaking to her in Railroad HQ. She’ll give you an RFID Device and ask you to head to a random location to procure a cache of items for the Railroad. This boils down to entering said location, defeating whatever enemies are within (or the enemies that are in your way, anyway), and hunting down the cache. It will be inside a secret room hidden behind a wall, which only the RFID Device can open. Collect the items inside and return to P.A.M. for your reward.

Jackpot is a renewable quest, with multiple locations for you to explore. Leave Railroad HQ and return after completing Jackpot and P.A.M. should have another iteration of it for you. If she doesn’t give you the quest immediately after, come back after a few days of doing other stuff and try again. Assuming he doesn’t have something else to tell you, Drummer Boy will alert you to P.A.M.’s requests as you enter Railroad HQ. There are (so far as I can tell) three missions in all.

When you complete one of these Jackpot missions, speak to Tinker Tom. He’ll gush over the discovery and reveal that he has been dealing with Ballistic Weave, which allows him to outfit normal clothing with a layer of protective armour. You can thereafter purchased ‘Armored’ clothing items from him that look like normal clothes but will actually protect you in a firefight. He’ll receive more items as you complete more missions. You’ll also gain the ability to craft them yourself via an Armor Workbench.

Climb the ramps from the lobby of Medford Memorial Hospital until you’re on the third floor. There’s a door in the east - the floor in front of it is missing - leading to a series of corridors. The cache is in a dead end.

One of the trickier caches to locate. Assuming you don’t have a jet pack handy, head down the alley on the west side of the building. A stairwell here leads to an adjacent rooftop where you can find a small jump over to a side entrance into Hub 360. The cache is in here. If you do have a jet pack you can pop open the elevator shaft on the second floor of the main building and jet up to the third floor, where the cache is located.

A groundside path up to the Fallen Skybridge
in Fallout 4.
Ruined Skyscraper

Your first problem is finding Ruined Skyscraper. To get here you need to locate the Fallen Skybridge, a stretch of highway owned by Super Mutants. There are a few ways up here, but the easiest way is to proceed to the intersection of highways to the south of Ruined Skyscraper (check the map above) and climb onto the northbound ramp. Ruined Skyscraper is near the end of the highway in the north.

Once you’re inside the Skyscraper you’ll face off against a few Super Mutants near the entrance, though most of the place is populated by Gunners. Fight your way through them, taking two elevators in the process. After the second elevator hits the sixth floor, walk straight ahead and take a left past the first door. You’re staring at the cache.