Strongholds and Sidekicks: A Guide to Establishing Domains & Hiring Help in DnD 5e

Last Updated on January 22, 2023

Recruiting hirelings (also known as retainers and sidekicks) and establishing a stronghold to serve as your party’s base (not to mention something on which to spend your vast reserves of treasure) are elements of Dungeons & Dragons that have, I think, fallen out of fashion somewhat in recent editions. 

While there are rules for building a base and hiring help in D&D 5e, they’re somewhat vague and scattered throughout different parts of the Dungeon Master’s Guide and Player’s Handbook. 

If you’re looking to fill out the ranks of your adventuring party, or looking to set up your own small kingdom, this guide gathers together the rules on strongholds and sidekicks from 5e, and fleshes them out with content from earlier editions of the game. 

Hopefully, it’ll make a case for why this underappreciated part of Dungeons & Dragons may have a place at your table. 

A Note on Old School Hirelings 

Back in the days of B/X (Basic/Expert) or Advanced Dungeons & Dragons, adventuring parties rarely headed into a dungeon alone. 

It was common – expected, even – for a party to spend a chunk of any petty cash they had on recruiting a number of hirelings, who filled roles ranging from mercenaries, spellcasters, and healers to torchbearers and porters (these were also the days when designers like Gary Gygax thought it would be a fun challenge to give players a treasure hoard with a value of 10,000 gp in copper pieces, making the process of hauling it back to town an adventure all in itself). 

Adventurers also tended to have lower hp pools, just one action per turn, and could be instantly killed by anything ranging from poison to falling into a pit trap. Having a few dozen peasants on hand to carry your bags and walk through suspicious doors first was just smart practice. 

Hirelings were cheaper to recruit and maintain in B/X D&D, with wages measured in months as opposed to days in 5e, although a skilled hireling like an Alchemist could run you as much as 1,000 gp per month. 

The rules for hiring help in 5e – such as they are – differ in a few key ways. Firstly, they’re more expensive and, as a chicken or egg kind of result, they tend to be more useful.

Also, I suspect the reason that hirelings are an aspect of the game that the rules of 5e tend to gloss over – probably in the hope that players don’t realize they’re there – is the action economy. 

In old-school D&D, only insanely over-leveled characters (a phase of play sequestered in its own section of the book, along with a warning equating to “don’t do this; it won’t be fun for anyone”) could ever take more than one action per round in combat.

Also, there were no bonus actions or reactions; you could move and do a thing and that was it.

Magic users also had smaller pools of spells, and characters had far fewer active abilities. 

As such, having a few more folk with the ability to swing a sword or cast a spell on your turn in combat was an effective way of leveling the playing field between two sides. 

In 5e, however, not only do player characters have the ability to do more things on each turn, but some classes can attack as many as five times in a given round. Sure, monsters can take more actions as well, but the overall action economy is balanced much more heavily in favor of the players. 

Adding 12 peasants to the mix – each of whom has a roughly 50% chance of hitting their target – means supposedly powerful enemies would just disappear underneath a hail of pitchforks. I mean… there’s nothing to say you can’t do this in 5e. 

I’d personally be delighted if the players’ solution to a local vampire problem was to hire the entire town, load them up with pitchforks and torches and go storm the castle the old-fashioned way. Sure, the combat would be a nightmare to run, but who am I to punish out-of-the-box thinking?

If you do want to discourage this sort of behavior, however, I would remind any party looking to cheese your adventure with a horde of angry peasants of the optional Morale rules on page 273 of the Dungeon Master’s Guide, which prompt Wisdom saving throws from monsters (and hirelings) when things get messy. 

But I digress… 

B/X D&D solved the “horde of peasants problem” by placing a limit on the number of people you could hire equal to your Charisma modifier, which is something I would definitely include in a retainer-heavy 5e game – at least until the players established a stronghold, that is. 

First, let’s look at how hirelings work in D&D 5e, and see how the way these rules were handled in older editions could help make them work a little better. 

Sidekicks and Retainers – Hired Help in 5e

The rules for hiring some extra help in 5e were incredibly light for quite a few years. Hirelings are listed under the Services subsection of the chapter on Equipment with two basic types – skilled hirelings cost a minimum of 2 gp per day, and unskilled hirelings cost 2 sp per day. 

The RAW basically leave it up to the dungeon master to determine the stats for these hirelings, how much they want in return for their services (the listed prices are given as a minimum), and which skills and abilities they bring to the party. 

The D&D Essentials Kit expands on those rules somewhat with the introduction of Sidekicks (which finalizes Unearthed Arcana materials released in 2018) intended to help support smaller parties. 

Sidekicks fall into three classes: Warriors, Spellcasters, and Experts. 

The Expert is a jack of all trades that prioritizes agility and supports your character in combat. They have Cunning Action, and their ability to help as a bonus action means they fall somewhere between a rogue and a bard. 

Spellcasters – also known as mages – can lean toward being either a cleric with a few healing spells or a Wizard with a bit more utility and damage. Personally, if I was making a mage for the party, I would find a way to randomize the spells that they have memorized for a bit of added unpredictability. 

Finally, Warriors can focus either on dealing more damage or on being a protection-oriented bodyguard for the party’s squishier characters. 

Sidekicks can level up (to 6th level) by following a track laid out in the Essentials Kit rules. 

It’s worth noting that Sidekicks must be humanoid (so befriending a gelatinous cube or a mimic is out of the question, I’m afraid) and that the rules don’t expect you to pay your sidekick a daily rate. I would rule that a Sidekick gets a full or half share of any treasure recovered while adventuring. 

If your party is looking to fill a hole in their abilities (a party of rogues and wizards in need of a tank, or the perennial gaggle of adventurers with no healer) then hiring a Sidekick is a great way to not only meet that need but also have a ready-made backup character on hand should one of them beef it in the middle of a dungeon. 

However, Sidekicks are definitely just adventurers of a lesser caliber than the PCs. What about if we just need to rustle up some obedient folk to hold the torches, stab the occasional goblin, or serve as mimic bait whenever the party finds a suspiciously unguarded chest? 

If you’re looking to recruit some more traditional hirelings, here’s a list I’ve put together using an amalgamation of 5e and B/X D&D rules. 

Each entry contains a link to a stat block, some additional abilities or skills, and you can use this excellent name generator to help you create a whole bunch of them quickly. 

Hireling Costs and Shares  

Capable Sidekicks and hirelings can really put a dent in your party’s budget. One way that adventurers got around this problem in older editions that I recommend players try in 5e is to purchase their services with shares. 

Basically, a sidekick or hireling may be willing to accept a lower per diem rate if they’re guaranteed a share of any treasure the party recovers.

If the hirelings can be convinced that there’s a big enough chunk of change awaiting them at the end of the adventure, they may be willing to reduce (or forego) their regular fees in exchange for a slice of the party’s pie. 

Retainers with more esoteric interests may also be tempted by the promise of spell components or magical items. A wizard looking to research new spells, for example, might choose to tag along (or more likely give you the loan of their hapless apprentice) in exchange for exclusive rights to a dragon’s teeth. 

Establishing a Stronghold 

One of my favorite things for players to do with their hundreds of thousands of gold pieces is to get on the property ladder (I always say D&D is a way to fulfil your wildest fantasies, like getting eight hours of sleep a night, hanging out with friends in person, and owning a house) by setting up a Stronghold. 

This can be accomplished in one of two ways. First, the party could move into somewhere that already exists. Abandoned dwarven mines, keeps overrun by hobgoblins, and temples to dark gods are all worthy candidates. The other route is to find an empty piece of land and build one from scratch. 

Either way, the players will likely have to follow roughly the same steps in order to get their new base up and running. 

Building a Stronghold: A Step-by-Step Guide 

1. Get Permission: If the Stronghold you’re building or restoring is located on land that falls under the control of a faction or powerful NPC, you’ll need to get their permission. In some cases, the Stronghold might also come with a Noble title attached to it, but will probably result in the ruler of these lands expecting you to keep the area free of monsters and bandits, or even come to their aid in times of war. 
2. Clear the Land: The surrounding area (or even the Stronghold itself) may need to be cleared of any threats, from wandering monsters to an infestation of Kobolds.
3. Design, Build, Restore: Whether you’re moving into an abandoned keep or raising a magical university from the ground up, you’re going to need to plan out your Stronghold, choose buildings and rooms, and hire the necessary engineers and laborers to carry out the work. There’s a list of 5e stronghold prices below, or you can get your DM to set prices for different features with a ruling that you need to hire one Engineer and a team of laborers for each 100,000 gp you plan to spend. 
4. Prepare for Settlers: No Stronghold is an island… except, you know, the ones built on islands- look, get off my back, ok? I’m doing a metaphor. If you want your new castle to become the focal point of a new town full of delicious, tax-paying peasants, you’re going to need to construct civilian buildings, clear farmland, and dispatch messengers to neighboring cities advertising the exciting opportunity to start a new life on the frontier. Once you’ve established a population of locals, you’ll need to hire guards to patrol your borders to prevent monsters from attacking, but you’ll also start being able to levy taxes and even a militia from your citizenry. 
5. Defend It: This is a tip I got from Matt Colville who always makes sure that, if the players get their hands on a Stronghold, it’s not really theirs until they’ve defended it against some kind of serious threat. 

I would rule that once they have a Stronghold, players lose any limitations on the number of hirelings they can recruit – although maybe it could still apply when they go adventuring. 

Construction Costs 

The 5e rules present the following costs and amounts of time taken to build various strongholds and additional buildings that could fit within one. 

Stronghold	Construction Cost	Construction Time
Abbey	50,000 gp	400 days
Guildhall, town or city	5,000 gp	60 days
Keep or small castle	50,000 gp	400 days
Noble estate with manor	25,000 gp	150 days
Outpost or fort	15,000 gp	100 days
Palace or large castle	500,000 gp	1,200 days
Temple	50,000 gp	400 days
Tower, fortified	15,000 gp	100 days
Trading post	5,000 gp	60 days

Class-Specific Strongholds 

I alluded to it earlier, but not every adventurer wants to set themselves up as the lord or lady of a castle.

Wizards might want to build a tower in which to continue their arcane research; a druid might want to start their own circle deep within the woods; clerics usually want to raise an impressive temple in their god’s name.

Work with your DM to figure out the necessary time and resources that a class-specific stronghold requires to build, as well as some benefits it might provide.

A Cleric’s temple, for example, could provide healing spells and potions, or the ability to cure disease. A wizard in their tower might be able to research new spells more cheaply or copy new spells into their spellbook for free.