Wide river, the other side immediately meeting extensive fortifications. It's a stunningly pretty fortress. There's a bridge. Narrow, stone, and swarming with both orcs and wolves. 

Oh, good. They would have been worried if it was suspiciously unguarded. How much space is there under the bridge?

Not none!

Well, Lúthien can stay a good ways back and downwind, and Malak will cross (invisibly, of course) by clinging to the side and bottom of the bridge then. Any reactions from the orcs or wolves as they do this?

Nope.

Then they will scale the walls - gate is shut, right?

Yep. Opens sometimes for people going in and out, though.

OK, they'll wait and follow someone in. Less likely to run into magical traps walking through a gate than on the outside of a wall. Also, climbing is tiring and they don't have their belt anymore.

They can walk in. It's a large, spacious courtyard, crowded - baby werewolves frolicking around, supplies being distributed, some forges, a blooming vertical garden, some orcs doing training exercises.

The garden was unexpected but maybe not terribly surprising.  The abundance of baby werewolves is weird, but local werewolves are different from the ones back home so it's not really weird.

Malak is quite comfortable moving through crowds, even when invisible. They don't bump into anybody on the way to the tower.

That gate's locked.

That is of little consequence. Hopefully there's nobody pressed up against the inside, because...

There is no popping sound like some wizards have, Malak was quite exacting on that point. They're now on the inside of that gate.

There's more orcs (none pressed against the door), and a staircase.

Well that's good, because Malak is pressed against the door and teleporting inside of orcs is bad for stealth. Did the blueprints Malak saw happen to include a dungeon or prison?

No, but there were storage cellars.

Those seem likely to have been turned into a dungeon.

Down the stairs they go.

Yep! They can tell by the smell, and the guards, and the tortured people chained everywhere.

Smell, check.  Guards, check. Just in case they don't manage to ever get the multi-target teleport working, how many locked or lockable doors are between the dungeons and the tower entrance?

How many tortured people still alive? Do any of them look anything like the images of Beren that Lúthien sent them? (They really should have thought to learn what the King looked like when they were in Nargothrond. They have been doing really badly at planning in this simulation, they wonder if that's just the lack of headband or if their mind is being tampered with otherwise.)

Five lockable doors, only two of them actually locked so far, all the cells are also locked, it is hard to tell at a glance if any of those people are alive but by rights none of them really should be. None of them have a special resemblance to Beren or, like, eyes, the absence of which might make it hard to notice if they did.

...That will make this trickier. How many prisoners total?

Sixty, seventy?

...They do not think there is any way they can get that many in one day, their reserves are not that... oh. No, best not think about that, just in case.

They head back out.

Unnoticed.

They don't feel like waiting around for another orc, so they teleport past the main gate. Cross the bridge by clinging to the side again.  Back to Lúthien.

"I know where he's most likely being kept, but I couldn't confirm that he was there and alive. There were a lot and they were all unrecognizable. I'm so sorry."

"Okay, so now we get them out. - how -"