Tuesday, September 22, 2026

World's Largest Rewrite: Mickity Thumpduck and His Gang of Halflings are Horrible and They Aren't Even Prisoners Here

#61: Hydra. The hydra absolutely makes sense as a prisoner. It is interesting that the OSE hydra lacks the ability to regrow severed heads, which is core to modern D&D’s hydra. Rolling on the variant table in the Overhaul gets “centipede hydra.” Ew. But it immediately made me think of the cellipedes we introduced earlier. The cellipede hydra is the broodmother of all cellipedes, and each time a head is severed, a new one will grow, sprouting a brand-new key, which fits into a lock somewhere in the prison. The cellipede hydra becomes a sort of dynamic solution to barriers that the PCs can "harvest" keys from, but may not want to kill, to avoid missing out on future keys. 

#53: Halfling. Like our recent hits on dwarves and elves, halflings have basic OSE entries and no dedicated Overhaul entry. As with those previous cases, we can use the Overhaul’s adventurer section to get a feel for the local halflings. 

  • Vice: Envy
  • Goal: Drugs and retirement
  • Why are they here: Utterly lost
  • Subtype: Brawling
  • Leader: Mickity Thumpduck; small eyes, leather cap; profession: justice; hidden miniature crossbow 
  • From: Gamwich village, in the Stenrind region

I’ve praised the Overhaul a lot during this series, but I can’t stress enough how well-calibrated the tables are to produce gameable output. I could run Mickity Thumpduck and his idiot gang of corrupt rent-a-cops right now, no further prep needed. They heard about the dwarven treasure, showed up hoping to get a cut, and are now lost inside the prison.

#57: Herd Animal. Stampede is the interesting mechanical hook here. The Overhaul (understandably) does not not have entries for mundane moose and oxen, but it does have one for telluric goats. These are mineral-eating goats, so pose a bit of a rust monster-esque challenge for adventurers. Rolling on the tables in the entry, we get bite effect of “target’s head and body must face north” and a reason to fight them as “whenever telluric goats appear, landslides and earthquakes are sure to follow.” This suggests a possible reason for the insecurity of this previous secure underground prison. The goats began (or exacerbated) the decline of the prison, and now roam its halls, seeking delicious ore. 

#75: Merchant. Yeah, this is a separate entry from Normal Humans. The stat block itself is not important. The entry instead sketches out the size and composition of a merchant caravan, so we’ll follow the same logic and place these merchants outside the dungeon. They’re probably keeping their distance from the brigands, hoping to buy weird stuff that adventurers extract from the prison.

These caravans are big. I rolled 1d20 for number appearing and got 10 merchants. That means we have: 

  • 10 mounts (one per merchant, implicitly?)
  • 20 wagons (2 per merchant) with corresponding beasts of burden
  • 40 L1 fighter guards (4 per merchant)
  • 2 L2-3 fighter lieutenants (1 per 5 merchants)
  • 1 5L fighter captain 
  • 2 extra animals 

These guys are a serious force! For exterior factions, the brigands might be stronger, if there are enough of them to form a fortified camp and score a genuinely high-level leader (we didn’t nail down William Osprey’s level in the brigand entry). But even if the brigands are stronger, the merchants could put up enough of a fight to make them think twice about throwing down. So it is an uneasy detente outside the dungeon.

#114: Squid, Giant. As we foreshadowed in the giant octopus entry, OSE delivers too much tentacle-based trauma for one game to sustain. These cephalopods are broadly similar, with the giant squid differentiated the most by some boat-attack-focused abilities. As we did with giant octopus, we’ll again use the Overhaul’s kraken table for inspiration, and we get “vampiric.” This is a bit of a play on the real-life vampire squid, or Vampyroteuthis infernalis (vampire squid from hell) if you’re nasty. Wikipedia articles are an excellent source of monster content, and there’s no reason we can’t raid this one. Look at the spikes on that hood. Imagine this guy dropping on an adventurer’s head and draining their blood, while using strobing bioluminescent light to confuse and stun would-be rescuers. We can even be really literal and associate these guys with the vampire we already placed in the dungeon.


An animated gif of a vampire squid unfolding and inverting itself to show its teeth-like profusions in a defensive or threatening manner


#110: Snake. Speak of the (vampire) devil, the next randomly chosen entry is for the snake. We already decided we wanted a giant albino snake to keep the vampire company, which brings Lair of the White Worm to mind. Snakes are nasty in OSE. We can size up the giant constrictor, and maybe give it a vampiric bite as well, depending on how we want to embellish the relationship between the vampire and the snake.

#136: Wyvern. From snakes to their heraldic descendants, wyverns. Like the snake, the wyvern has save-or-die poison. The Overhaul, interestingly, doesn’t treat the poison sting as a default feature. Rolling on the variant table, we get “Gulper: Neck sack, wattle, one nostril.” Imprisoned for its ravenously hungry behavior. 

#90: Pegasus. This far into this series, we have a lot less blue sky design, a lot more filling in spaces between already established monsters and factions. Pegasi are potential flying mounts for the jailers; the fighter jets to the bomber that is the roc we found earlier. They serve lawful characters. Perhaps the pegasi are no longer willing to aid the dwarves, sensing that some of them are compromised? 

#87: Ogre. They hate neanderthals. Otherwise, they’re bog-standard ogres. But the Overhaul can give us a tailored ogre.

  • Name: Durl
  • Feature: Thick forehead ridge
  • Weapon: Hook and chain
  • Crime: Despoiled sanctified ground
  • Type: Fumeguts, leaks black fumes, twice per day, opaque fog, 30’ radius, 10 rounds
Locked up for farting in church. Sometimes these entries write themselves.

#102: Salamander. Ya got your hot lizards and your cold lizards. They are mostly similar, although flame salamanders are neutral, and frost types are chaotic. We'll choose the frost type as more fitting prisoners. The Overhaul directs to elemental spirit (where our gnome came from) and suggests barbegazi, which is more evocative than "salamander." These guys are "despised yet treasured local rivals" who look like "old, dark-eyed, serious men and women." That fits with a sort of frost witch folklore.




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World's Largest Rewrite: Mickity Thumpduck and His Gang of Halflings are Horrible and They Aren't Even Prisoners Here

#61: Hydra. The hydra absolutely makes sense as a prisoner. It is interesting that the OSE hydra lacks the ability to regrow severed heads,...