Flails 5e — Magic and Mundane for Every Tier of Play 

Whether you’re looking to replicate the blood-curdling menace emitted by the Witch King of Angmar as he faced down Eowyn at the Battle of Pelennor Fields or just recreate the general vibe that happens when I hit the dancefloor after seven too many beers at a wedding, you’re in the right place. That’s because today we’re going to be talking about flailing… I mean flails. You get it. 

We’re going to take a closer look at this weapon, examine how it works in Dungeons & Dragons 5e, and show you some of our favorite official (and homebrewed) options for magical flails. Hopefully, this should help you inject a little of the old chaotic ultraviolence into your campaign, should you wish to do so. 

What’s a Flail?

In both real life and Dungeons & Dragons 5e, a flail is a heavy ball sometimes covered in spikes and connected to a handle by a length of chain. The wielder then whips the ball around harder than a particularly viscous booger on the eraser end of an exam pencil, using centripetal force (Or perhaps centrifugal force? You know, momentum) to smack that ball into someone they don’t like very much, causing an outrageous amount of damage. 

It’s like if a Skip It had a baby with the 90s teen’s second most essential fashion accessory. Or like nun-chucks for white people. 

Speaking of white people, as anyone who’s ever tried to do poi (or is just, like, really bad at yo-yo-ing) can attest, whanging a lump of something heavy around on the end of a length of chain, rope, or string makes for a super rowdy weapon. 

Okay, But Why a Flail?

So, that’s what a flail is. Honestly, the “what?” certainly begs a “why?” So why the flail? Were medieval weapons too tame? Did the bloodthirsty psychopaths rampaging across historic battlefields find things were getting a little too stale and predictable? 

Well, in real life, the flail was just one of many ways that knights and soldiers in the late medieval period came up with to deal with the problem of real-world Armor Class. By this point in history, the art of blacksmithing had become so freaking advanced that most of these medieval knights found themselves routinely facing opponents walking around inside full-body suits of plate mail armor. 

It’s an experience I’m sure my cat identifies with a great deal as he throws himself once again into the cupboard where we keep his tinned food. It must have been almost as demoralizing for medieval knights to find themselves and their comrades being casually massacred by giant, impenetrable tin cans.

By the mid-15th century especially, a suit of full plate available to knights in Western Europe could withstand just about everything from direct hits with a sword or axe to crossbow bolts. Because the electric can opener (truly the demise of heavy infantry on the battlefield and of the last shred of control I have over my cat’s behavior if he ever learns to use one) wouldn’t be invented for a full 400 years, people looking to take down a knight needed the next best thing: massive amounts of blunt force trauma leading to massive internal bleeding, concussion, and disorientation. 

Bonk.

The idea was that, if you couldn’t get inside the armor of the knight you were trying to gently persuade to go die in a ditch somewhere, you could at least shake up everything inside that armor like a can of V8 you found sitting on a shelf since 2002. The result, in both cases, is a thick, reddish sludge that you almost certainly shouldn’t be drinking, regardless of its surprisingly high nutritional content. 

If knights were the tanks of medieval warfare, flails were the rocket-propelled grenade.

How Do Flails Work in DnD 5e? 

In D&D 5e, flails are a remarkably simple weapon. 

Flail

  • Type: Martial Melee Weapon
  • Cost: 10 gp
  • Weight: 2 pounds
  • Damage: 1d8 bludgeoning

Proficiency with a flail allows you to add your proficiency bonus to the attack roll for any attack you make with it.

The flail does a little bit more damage than its less chain-related cousin, the mace, at the expense of requiring martial weapon proficiency to be useful, and that’s about it. It’s not versatile as the longsword, battleaxe, or warhammer (probably its closest relation), meaning that if you want a strictly optimal choice, there’s no reason you should be picking this weapon over any of its martial contemporaries. 

But that’s not why you’re here. 

People who choose their weapons based on their optimal damage output or versatility aren’t the kind of people who deserve to wield the skull-smashing, bone-bashing, shield-shattering awesomeness of the flail. 

Come on. How do you not want one of those? 

When paired with a shield or an off-hand weapon (and the Dual Wielder feat), a flail is a perfectly solid mechanical choice, and you’re going to look absolutely terrifying. But the only thing that’s more terrifying than a murderous psychopath with a flail is if that flail also glows or smacks you into another dimension or whatever. That’s why the meat of this guide is going to be about magical flails with a wide enough array of options that you can outfit a flail enthusiast of any experience level with something to bring joy to their hearts and looks of pure horror to the faces of people who cross them. 

Also, because there are only, like, two official flails spread across the various D&D sourcebooks (the Vicious Flail and the Flail of Tiamat), we’re also going to be making up a few of our own homebrewed flails for use in your games (with your DM’s permission, of course). 

So what are we waiting for? Let’s get flailing. 

No, not like that! Weren’t you listening!?

Low-Tier Flails (Levels 3-5)

I’ve said it before, and I’ll say it again: +1 magic weapons are a snoozefest. Not only are they boring mechanically, but unless you handle them correctly by making them interesting parts of your world, tying them into your history and ongoing campaign narrative, they’re going to make about as much emotional impact on your players as a boiled egg they ate in 2007. 

Therefore, if you’re considering giving a player a magical flail, make sure you give it some aesthetic spice, a cool name, or an interesting effect. When it comes to this latter point, may I humbly present these two options? 

Vicious Flail 

Weapon (flail), rare

When you roll a 20 on your attack roll with this magic weapon, the target takes an extra 7 damage of the weapon’s type.

Proficiency with a flail allows you to add your proficiency bonus to the attack roll for any attack you make with it.

In the long run, this weapon is mechanically worse than a basic +1 magic weapon, but it’s way cooler because critting and doing a nice chunk of extra damage is the kind of thing people remember.

I would still probably make this a +1 magic weapon as well, however. And maybe give an additional effect to the critical — like removing an enemy’s damage resistances for a round or stopping them from taking reactions. Just to make it feel a bit more special. 

Thunderskull Flail (Homebrew) 

Weapon (flail), rare (requires attunement)

This flail is made from the petrified skull of a blue dragon wyrmling with eyes and mouth set with glittering turquoise stones. The air around the weapon is heavily statically charged. 

On a critical hit, this flail deals an additional 1d8 thunder damage (on top of the usual 2d8) and emits a peal of thunder audible up to 300 feet away. 

Once per day, you can slam the flail into the ground to force all creatures in a 10-foot radius sphere centered on yourself to make a DC 12 Constitution saving throw or take 3d8 thunder damage and be knocked prone. Creatures that make a successful saving throw take half damage and are not knocked prone. 

One of the easiest (and most “balanced”) ways to homebrew a magic item in DnD 5e, according to the Dungeon Master’s Guide, is to make the item replicate the effect of a spell — in this case, Thunderwave, with the area of effect slightly modified and the damage upcast to 2nd level. 

Mid-Tier Flails (Levels 6-14)

For mid-tier flails, we get to have a little more fun and experiment with some more powerful, versatile options. 

Sainted Censer (Homebrew) 

Weapon (flail), very rare (requires attunement by a cleric or paladin)

An ornate golden censer that doubles as a flail. You gain a +1 bonus to attack and damage rolls made with this flail. 

A number of times per day equal to the wielder’s proficiency bonus, the wielder can spend an hour blessing the censer in the name of a saint or deity. Once blessed and lit, the incense inside the censer burns for 1d4 hours and confers all that stand within 10 feet of it (provided there is no strong wind to blow away the smoke) one of the following benefits, depending on the saint in whose name the flail was most recently blessed. 

  • Saint Malovar (red smoke): All weapon attacks made by creatures friendly to the censer’s wielder inflict +1d4 radiant damage while inside the cloud. 
  • Saint Bulkward (green smoke): All creatures friendly to the censer’s wielder gain +1 AC while inside the cloud. 
  • Saint Marwa (gold smoke): All creatures friendly to the censer’s wielder gain 1d4 temporary hit points per round while inside the cloud to a maximum of 10 + the wielder’s character level. 
  • Saint Celestine (blue smoke): All creatures friendly to the censer’s wielder have advantage on saving throws against becoming magically charmed, paralyzed, or restrained while inside the cloud.   

This flail provides more opportunity for a cleric or paladin to support their allies with a semi-aura mechanic that can be switched up depending on what the party needs most, but it is balanced by the physical limitations of having to stand inside the smoke cloud (which is susceptible to high winds) and the time that needs to be invested in preparing the aura. 

Whistling Flail (Homebrew) 

Weapon (flail), very rare (requires attunement) 

A large piece of bleached white bone carved with esoteric symbols and perforated with dozens of small holes. When spun around at the end of its chain, the air passing through the holes creates an eerie whistling sound. 

If you spend a bonus action spinning the flail up to speed, you gain a +2 bonus to attack and damage rolls made with this flail. You can also spend an action (on the same turn you bring the flail up to speed or a subsequent turn if you have not yet taken the attack action with the flail or spent your action doing anything that would require you to stop spinning the flail) to try to hypnotize a creature that can see and hear the flail with its mesmerizing sound. 

The target must succeed on a DC 10 (+1 DC for each turn you have spent since spinning up the flail and continuing to spin it; maximum DC of 18) Wisdom saving throw or be stunned until the end of your next turn or until the flail stops spinning. A target may repeat the saving throw upon taking damage. 

I like a weapon that heavily implies how it’s supposed to be used, and this whistling flail very much suggests you’re supposed to dazzle a big dumb enemy with its cool sound and then smack them over the head with it. 

High Tier: The Flail of Tiamat (Levels 15+)

If you’ve reached the highest levels to which a hero or villain can aspire, there’s only one flail for you. 

The Flail of Tiamat

Weapon (flail), legendary (requires attunement)

This magic flail is made in the image of Tiamat with five jagged heads shaped like the heads of five different chromatic dragons. You gain a +3 bonus to attack and damage rolls made with this flail. When you hit with an attack roll using it, the target takes an extra 5d4 damage of your choice of one of the following damage types: acid, cold, fire, lightning, or poison.

While holding the flail, you can use an action and speak a command word to cause the heads to breathe multicolored flames in a 90-foot cone. Each creature in that area must make a DC 18 Dexterity saving throw. On a failed save, it takes 14d6 damage of one of the following damage types (your choice): acid, cold, fire, lightning, or poison. On a successful save, it takes half as much damage. Once this action is used, it can’t be used again until the next dawn.

Proficiency with a flail allows you to add your proficiency bonus to the attack roll for any attack you make with it.

Made in the image of the five-headed queen of evil dragons, the Flail of Tiamat is probably one of the more heavy metal D&D magic items out there. Aesthetics aside, being able to swap between five of the more common elemental damage types is a great way to make sure enemies aren’t going to be able to make the most of their resistances. 

Lastly, the 90-foot breath weapon with damage output somewhere between a young and adult dragon is nothing at all to sniff at. You may find, however, that members of the cult of Tiamat tend to keep showing up demanding their cool flail back — or worshiping you, which is probably worse.