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What Monty Python Can Teach You About Tactics in Dungeons and Dragons

Suffering a defeat in battle during a Dungeons and Dragons session isn’t the most fun thing in the world, if we’re being honest. Even if you’re not a murder-hobo, you still like to come out on top. Nailbiters are fun, but when the final nail is driven into a PC’s coffin, it is decidedly less so.

But to quote the great philosopher Alfred Pennyworth: “Why do we fall, sir? So we can learn to pick ourselves back up.”

I’m not suggesting your PCs make a habit of falling down (read: losing); quite the opposite! What I hope to accomplish in this post is to equip your characters with a few tactical options that will help them first to stand up, and then to stand strong.

And we’ll use Monty Python and the Holy Grail to illustrate each step!

Step One: Retreat

It is the consensus among a few of the Nerds on Earth writers that the tactical retreat is an underutilized skill in Dungeons and Dragons.

Sometimes the battlefield evolves in a way you weren’t expecting or prepared for–like when previously unseen enemies make their presence known. Other times you just make a tactical blunder and need to withdraw and reconsider your approach. And sometimes you walk into a fight that you’re just not leveled for yet!

Any and all of these represent reason enough to fall back. It might wound the pride of some, but you’ll live to fight another day!

Look at a retreat not as a defeat but as a recon mission that had a bit more enemy engagement than anticipated. If you can get clear of the fight, you’re now equipped with information you didn’t have when you first stepped into it. Knowledge is power, after all.

When King Arthur and his knights came across the dreaded Rabbit of Caerbannog, they initially rushed upon the seemingly meek creature. This spelled a bloody doom for a handful of his number! They underestimated their enemy and needed to retreat and reconsider their approach.

Step Two: Rethink

Now you’ve got intel! That intel should inform and affect your second attempt–whether that attempt happens sooner or later.

So put your heads together and come up with a plan.

  • What seemed to work?
  • What didn’t?
  • Do you need to prepare new spells that might swing the tide of battle before trying again?
  • Will waiting (say, for nightfall) provide a change of circumstances that work to your advantage?
  • Can you gain even more intel with an honest-to-goodness recon mission?
  • Can you set traps or an ambush?
  • Is there any equipment or ability on your character sheet that could prove uniquely useful?
  • Is this fight one you can avoid altogether?

It is said that the definition of insanity is doing the same thing over and over again and expecting different results. Leverage your INT scores and do something different in the hopes of working towards the desired outcome of victory!

But beware: Not all intelligence gathered has the shelf life of a Twinkie. Your first move might have put the enemy on a higher alert or they might have called for reinforcements after you withdrew. Stay sharp and don’t get too cocky about what you know or it could end in further disaster!

Upon retreat to a safe distance, the knights recalled that a member of their party carried with them the Holy Hand Grenade of Antioch, which just might be able to turn the tables in their favor!

Step Three: Retry

Now that you’ve retreated and reevaluated, it’s time to retry! Get back in there and do work!

You may have been surprised or overwhelmed the first time, but you’re better prepared this time. If the first encounter didn’t take place on your terms, the second one absolutely can and should if at all possible.

You’ve drawn up the play on the little whiteboard on the sideline, so now it’s time to execute. Part of your success is going to depend upon communication during battle. Instead of everyone pretty much doing their own thing while working towards a shared goal, get everyone in concert with one another working towards that shared goal. Teamwork makes the dreamwork!

Use Free Actions to call out to one another; sharing information and continuing the conversation you had in Step 2 as the battle evolves. The beginning of a pitched fight doesn’t signal the necessary end of strategizing. You just move from being proactive to being reactive – a shift that takes place in the midst of literally every planned military maneuver ever.

“And Saint Attila raised the hand grenade up on high, saying, ‘O Lord, bless this thy hand grenade, that with it thou mayst blow thine enemies to tiny bits, in thy mercy.'” And on the count of three (“five is right out…“) the newly devised tactic was executed – and to great results!

Step Four: Repeat (If Necessary)

The worst that could happen is the death of a PC or a TPK, but hopefully you’re smart enough to avoid such things in the absence of unforeseen and uncontrollable circumstances. The dice always play a major part in the story we’re telling, after all!

Even if the plan you came up with during Step 2 fails during Step 3, you know you can always resort back to Step 1 in the event of repeated disaster – which is the second worst outcome, but it has its benefits, as we’ve seen.

Sometimes you just gotta pull a Steve Rogers (“I can do this all day” ) or a Commander Peter Quincy Taggart (“Never give up. Never surrender.”) And pulling a tactical retreat, regrouping, rethinking, and retrying isn’t giving up in the least. It is the opposite: extra effort expended in the pursuit of ultimate victory.

Retreat. Rethink. Retry. And win the day.

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