The Situation

One of my players angered a very dangerous guild of assassins, by killing one of their members, that of course got him a nice bounty for his head. In a attempt to deceive the guild, they took the corpse to their temple and said it was a monster that killed the guy.

The member of the temple simply took the corpse and said only one thing: "Shar always remember". I described that in the entrance of the temple that was a crow with red eyes watching them.

After that particular encounter I made sure to put omens to remind them that assassins are after one of the party members. They actually spotted crows with red eyes 5 times after that, and always in their boat.

So, now I get to my dilemma. I've planned for the assassins to sent a rakshasa to do their bidding. My players have dropped their guard and sent NPCs to recruit new sailors for their ship, so the Rakshasa used this opportunity to infiltrate the ship, study them and is waiting for the right moment to strike.

And that moment came. Right now my players are sailing through the seas and are currently without any of their magical weapons.

The Party

It is a 7th level group. The party has a Monk, Wizard, Barbarian, Rogue, Ranger and a Bard. We have been playing together since the start of the year and they started at lvl 1. And all of them are very good players, hard to challenge. They know the system and know how to use it in their favor. (They are all playing evil characters, so I was very surprised when, given the circumstances, they dropped their guard so hard!)

My "DM's Dilemma"

It is the right time for the Rakshasa to strike, but at the same time I'm afraid that it is going to be a very unfair fight, since they have no way to damage this fiend.

  1. Is it a fair encounter to run, considering the situation?
  2. Should I run this encounter now or wait until they have at least a fighting chance?
  • \$\begingroup\$ #1 is an answerable question here, assuming the necessary details are provided. For #2, what you "should" do is largely opinion-based. What do you actually want to do? \$\endgroup\$
    – V2Blast
    Jul 17, 2018 at 17:38
  • 1
    \$\begingroup\$ The edit has helped this question, but it still looks pretty opinion-based to me, because the core question is "is this fair?" The concept "fair" is pretty hard to talk about in a non-opinion-based way. If you are able to add more specific criteria (for instance, "is this encounter likely to result in a TPK?"), it would go a long way toward making this more objectively answerable. \$\endgroup\$
    – A_S00
    Jul 17, 2018 at 19:18
  • \$\begingroup\$ I still think this is still heavily subject to opinion (some tables are fine with regular TPKs), but something that stands out to me is that a rakshasa is very powerful against a 7th level party. Why that creature? What about the rakshasa's motivations? Has he been hired to kill the whole group or just the one character that killed one of the group's members. \$\endgroup\$ Jul 17, 2018 at 19:47
  • \$\begingroup\$ I've voted to reopen because I have a good answer which I am waiting to post. \$\endgroup\$
    – Dan B
    Jul 17, 2018 at 19:48
  • 2
    \$\begingroup\$ @filipedfontes SE doesn't do "discussion", it does question-and-answer. That's why opinion-based questions frequently get locked down. \$\endgroup\$
    – T.J.L.
    Jul 18, 2018 at 19:08


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