In SoC, a main quest line that had us fighting Tristayn Olliven with the objective to free prisoners came up last night. It's actually a two piece map, with the two sections connected by a portal (portal requires 1 movement point to go through, not an action).
The prisoners are treated as heroes, and once freed will get 2 move actions of 4 movement points per action, with the instructions to travel from one map section to another through the portal and then head for the nearest entrance.

One of Tristayns instructions that comes up is to have him switch places with the furthest hero.
Some monsters say to specifically go engage prisoners.

The questions that came up:
When Tristayn swaps with furthest hero, is that furthest in that map section? Or in both? Would his teleport swap take him to the other section?
For monsters with an engage prisoner instruction, if the monster is in one section and all prisoners are in the other, would they skip that instruction or would they head for the portal and walk through in their attempt to engage a prisoner?

Just for reference, the quest in question is called "Missing in Action".

Here are my opinions on your questions (with the caveat that I might be wrong, but it's my best guess):

15 hours ago, Kaaihn said:

When Tristayn swaps with furthest hero, is that furthest in that map section? Or in both? Would his teleport swap take him to the other section?

This already is tricky to answer. Again as a reference, the activation of Tristayne in question:

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TRISTAYNE_6_EFFECT
"Tristayne Olliven immediately switches spaces with the farthest hero."
TRISTAYNE_6_0
Action: Attack the hero within 3 spaces of this monster with the lowest awareness.
Action: Attack the hero within 3 spaces of this monster with the lowest awareness.
Action: Spot the closest hero.

So, the first problem is, that there is no definition of the word farthest or furthest in the RtL rules. One might assume logically, that all distances between figures are measured by counting spaces, and I think this is the intent.

It might be a bit of a leap, but to further this assumption, I'd use the POD Rules as reference, because the RtL monster activations are a clear evolution of the activation cards from one of these expansions. There we have a definition of furthest:

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Furthest: The target that is the greatest number of spaces away from the monster.

Based on this, we have a rule to determine the target, the hero who is the greatest number of spaces away from the monster. The problem is, that we usually can't count spaces to a figure a not physically connected section of the map. This however depends, on how figures can travel from said sections to other sections. Broadly speaking, if there is one token on each section, which is defined as adjacent to the other I'd say you could count spaces. But this is a very special case. For reference, here is the description of the way to travel from one section to another:

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SOC_Q_MIA_RIFT " A figure on or adjacent to a rift may spend 1 movement point to remove that figure from the map and place it adjacent to the other rift. "

So in this case, the "rifts" allow a figure to transfer itself from andadjacent space to an adjacent space of the other rift. There are however no adjacent spaces between the 2 rifts.

In this case I'd say, that each time Tristayne would try to count spaces to a hero on another section, he can't reach this hero, and the result would be void. Because of this I'd say Tristayne mechanically can't swap places with a hero on another section, even though he might logically be furthest away from him*.

15 hours ago, Kaaihn said:

For monsters with an engage prisoner instruction, if the monster is in one section and all prisoners are in the other, would they skip that instruction or would they head for the portal and walk through in their attempt to engage a prisoner?

Another tricky question. For reference here are the Zombie activation instructions:

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SOC_Q_MIA_ZOMBIE_ACTIVATION_MINION
Action: Engage the closest prisoner.
Action: Attack the adjacent hero with the lowest willpower.
SOC_Q_MIA_ZOMBIE_ACTIVATION_MASTER
Action: Engage the closest prisoner.
Action: Attack the adjacent hero with the lowest willpower.
Action: Use Grab on the adjacent hero with the lowest might.

Unlike with the word furthest, engage is luckily is defined in the RtL rulebook.

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ENGAGE
When engaging, a figure is trying to get adjacent to a target. It performs a move action and moves toward the target (see “Toward” on page 18), stopping when it is adjacent or when it runs out of movement points.

To find out more about the activation, we have to look up the keyword toward on page 18:

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TOWARD
When moving toward a target, a figure is attempting to decrease the number of spaces between it and the target. During the movement, the figure can increase distance if by doing so, the end result allows it to be closer.

However the problem is again, that, while it is used pretty often in the rulebook, closest is not strictly defined (like furthest). Once again I'd use the definition from the PODs:

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Closest: The target that is the fewest number of spaces away from the monster.

Here we have the same problem as in Tristayne's case: Since we can't get a legal number of spaces between a Zombie and a prisoner if all of them are on different sections, there is no valid target to engage toward. While it would logically make sense, that the Zombies would follow the prisoners through the rift, mechanically they could not choose a prisoner on the other side as a valid target*.

While I don't think the conclusions I draw here are great, they appear to be the mechanical correct intrepretation. At least, until you consider this:

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SOC_Q_MIA_CAPTIVE_ACTIVATE
Each freed captive gains two actions, has a Speed of 4, and performs the following:
Action: If adjacent to a monster, move 1 space toward any Entrance.
Action: Engage any Entrance.

Since we have to activate the prisoners in the same way we activate monsters, the prisoners would never be able to engage an entrance, since these are on the other section of the map. This clearly can't be intended, as it would clearly break the quest.

This means all of my prior conclusions seem to be void. Mechanically, the only way I see to fix this is to treat all spaces adjacent to one rift as adjacent to all spaces adjacent to the other rift.

If this is the case we could "sort of" count spaces, and the problems would be avoided.

*So my final conclusion and answers to your questions is this:

Yes, Tristayne can swap spaces with a hero on another map section.

Yes, Monsters can engage prisoners, that are on another map section.

I guess this is another case of Rules as intended vs. rules as (not) written. In this case my gut feeling is that we have to go with the rules as they were clearly intended, as the quest would otherwise be massively broken.

Edit:

Just to elaborate a bit more on the rules of this quest:

Strictly speaking, the Zombies would never even target a figure, because they would engage prisoners . The villager tokens on the map are however called captives:

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SOC_Q_MIA_PLACE_CAPTIVES
You enter a small pocket of the dark domain. All around you, prisoners are bound to the walls and floor. A few see you, but they do not react—these have been broken long ago and now exist without hope.
Place 8 villager tokens as shown, and place 1 fatigue token on each villager token to show that it is bound. These are captives.

Not to confuse with the other villager tokens, which are placed earlier in the quest:

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SOC_Q_MIA_PRISONERS_FAKE_PLACE Place {0} villager tokens. These are prisoners.

This are the rules concerning the captives:

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SOC_Q_MIA_CAPTIVE
Captives are treated as hero figures and do not roll defense dice. If a captive suffers 5 or more damage during a single attack, discard it from the map.
As an action, an adjacent hero can free a captive who is bound.
At the end of each round, the freed captives activate.

On the other hand, the objectives and the dialogues once again refer to prisoners:

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SOC_Q_MIA_ESCAPE_CAPTIVE
For each prisoner on an Entrance, place that prisoner in the heroes play area.
Are there more than {0} prisoners in the heroes play area?

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SOC_Q_MIA_OBJ_4
Free the prisoners

To be honest, from a rules consistency standpoint, this quest is a horrible mess.

I appreciate the detailed breakdown quoting the quest! There is at least one more screwy mess of behavior in this quest that we came across as well. A master zombie attacked the closest captive, which was one that wasn't freed yet. The master grabbed the captive, causing Stun. So, following the way this quest works, and the way stun works, captives don't activate and get actions until they are freed. So, that bound captive sat there stunned for 3 turns because he didn't get to activate to clear the stun. Kind of strange.

We played it following the common guidance that monsters don't use special features in RtL unless specifically noted. So, no open doors or portcullis, no going through rifts, etc. That means Tristayn's teleport stayed in that one map section. It was pretty brutal honestly. Tristayn gets 2 attacks per turn because of ravage, and since he wasn't leaving the room at all he was mowing down captives. Combined with the 5 zombie spawns plus the shambling colossus, we felt lucky we managed to save 2 out of 8. There were just two many attacks on captives happening before it was possible to smash the monsters that are there from the start. The offset was that we left the beastmaster with his wolf choke-pointing the nearest entrance to the rift, so he was solo'ing all the zombies each turn as they appeared, giving captives a clear run to the entrance once they got through the rift. I'm not sure that would have worked as well if the zombies would have been following their instructions to continuously head for the prisoners through the rift. They wouldn't have hung around clumped up to be slaughtered.

I think the whole thing would have flowed better if we had played it the other way, teleport working across both sections and zombies able to walk through the rift. Definitely a weird one. If you think of the rift in this one as an open doorway instead of a special terrain feature, the whole thing does make sense I guess.

We weren’t even sure if the Zombies would attack captive prisoners as it seemed really unlikely that any in the top half would survive.