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[The_Warlock]

Oh yes. I'm familiar.

And to be fair, my last big campaign was a lot less sandboxy, there was a definitive foe with a massive train of clues and prophecies for them to follow.

I'm partially to blame for training them to second guess, however, since I made sure that when they made abysmally poor choices, they suffered the consequences. Keep in mind, they didn't make catastrophic choices all the time, nor did they have many true failures, nonetheless, from their perspective the painful successes seemed like failures.

Rather than examine some of the root causes of their failures, they simply started second guessing any possible action and trying desperately to garner foreknowledge before doing anything.

And then attempting to overplan for so many contingencies that they often lost sight of the actual goal.

I used both in game and out of game to slowly rectify this.

1) A henchwoman, bored out of her mind, basically looked at them during one particularly useless session and said, "Are we going to DO anything? Because if we don't, they still are. Let's just do it the Demon Way. You can't possibly know everything that the enemy can bring to bear, so pick your target, get as much relevant info on it, and do whatever it is that needs to be done. The worst that's going to happen is you are going to die. Rather than have a contingency for every thing you don't know they can do, have a contingency for DEATH, and let's get on with it."

2) This was followed up sometime later by a firm DM directed discussion as a group (as well as individually with the players who seemed most paralyzed by the juxtaposition of risk vs reward) that they were adventurers and heroes.

Their meat and drink was taking risks that ordinary people wouldn't. In addition, there would almost never be a time where some action of consequence didn't involve serious risk. But there was a difference between taking heroic risks for some worthy goal, and being downright stupid.

Attacking the fortified enemy stronghold while playing to their skills and powers - still risky. Charging up to the front gate with your sword out, an insult on your lips, and no idea of what to do beyond that - an invitation for rocks to fall from the sky, you die, no save.

They then started to actually look for ways to do things actively, rather than react to the movements of the enemy. They also generally played to their own strengths and did their best to have escape plans, rather than trying to second guess every action or divine every possible way their enemies might counter them.

They occasionally backslid, but never as badly, and became unholy terrors, even when they were caught off guard and unprepared.

This is a group who, after their "We are Heroes!" revelation, faced a mixed clockwork/normal undead lich, and watching it trap the party rogue inside a Prismatic Sphere with it to kill him at it's leisure, were able to, on the fly, without any foreknowledge, bring all the appropriate spells to bear, IN ORDER, to drop the sphere before the Lich got it's next turn.

The same party who some years prior got their butts handed to them by a half-marilith demon, and began an unorganized retreat, and nearly had 4 characters die because they were arguing about who would be the last one through the hole that the demon couldn't fit through - while the demon hacked at them.

And then spent nearly two session arguing about how stupid it was, demanding that a "retreat order" be developed depending on the type of foe kicking their butt, and then scattering like frightened rats in the next two encounters rather than follow their carefully laid out "escape procedures."

So, my suggestion, make sure the players are clear on the whole point of adventure. And if necessary, provide an in game NPC who watches one of these conversational debacles and basically calls them all on it.

It worked for me, though your mileage may vary.