Leveling Up in DnD 5e: XP vs Milestone Leveling – This Is How To Decide

Last Updated on January 22, 2023

Leveling up is undeniably one of the most satisfying parts of the Dungeons & Dragons 5e experience. Your character grows in power, becomes more survivable, and unlocks new abilities that allow them to face increasingly dangerous threats. 

Exactly how and when characters level up can be determined in a number of ways. And, like just about every aspect of D&D, there are competing views on which one is “best”.

As with most of these arguments, the answer depends on your players, the type of game you like to run and ultimately what you, the dungeon master, decide you like best. 

In this guide, we’re going to break down the three main ways to track character progression in D&D 5e – XP, Milestone, and Level Advancement without XP – laying out how they work and why you might want to choose one over another. 

Using XP – Classic, Player-Driven Advancement 

XP is the original way in which characters gained levels in early editions of D&D. 

Interestingly enough, up until 2nd Edition, characters gained XP both by defeating monsters and recovering treasure – with each gp worth of loot brought back to town granting a point of XP. 

In Dungeons & Dragons 5e, while treasure is now considered its own reward, defeating monsters (either by killing, routing, or capturing them) is still the main way of gaining XP.

However, 5e also introduces the idea that non-combat encounters also grant XP based on their difficulty and risk compared to a combat encounter. 

Chapter 3 of the Dungeon Master’s Guide breaks down encounter difficulty into four brackets: Easy, Medium, Hard, and Deadly. 

Easy Encounters don’t tax characters’ resources too heavily and, while they might lose a few hit points or burn a spell slot, such an encounter isn’t meant to create a significant hurdle to the party’s progress. 

DM’s Tip: I tend to use things like patrols and guards as easy encounters. A good easy encounter doesn’t question whether the adventurers will win, but rather if they can do so without depleting their resources so that subsequent encounters become riskier. 

Medium Encounters are a step up in terms of danger. Characters might have a few close calls, and some of the weaker (or more foolish) ones might get knocked unconscious.

The party will lose hit points, spell slots, and probably need to spend time healing. If things go poorly, they may need to decide between resting (and risk a random encounter) or pressing on. 

Hard Encounters definitely have the potential to break bad for the adventurers. More than one hero will probably fall unconscious, high-level spell slots will be burned, and there’s a slim chance someone will die. 

DM’s Tip: when putting a hard or deadly encounter in front of my players, I try to always make sure that they have an avenue of escape, or have made an informed choice to wade into battle. Character death should always feel like it could have been avoided if only the players weren’t being so foolish.

Deadly Encounters push player characters to their limits, and could easily result in character death (or worse, a TPK!). A direct approach is rarely likely to work and usually, only quick thinking and sound tactics will avoid defeat. 

These levels of encounter difficulty are presented as a way to use the Challenge Ratings (CR) and XP values of monsters to build combat encounters. It’s a pretty flawed system, as some monsters (like Shadows, which drain characters’ Strength, risking a death spiral) punch well above their CR, and others (like a magic user without the necessary minions to prevent the barbarian from running straight across the map and obliterating them in one round of combat) can feel decidedly underwhelming. 

Still, using this chart to compare character level to encounter difficulty as a rough guide (don’t meticulously add up every monster’s CR; just build the encounters you like and then decide whether they’re easy, medium, hard, or deadly) is a good rule of thumb for distributing XP. 

Awarding XP for Non-Combat Encounters 

One of the best parts about XP-based advancement in 5e is the fact that the game acknowledges you can gain experience by doing things other than slaying monsters. 

Any situation where there are stakes for failure can result in the players’ characters gaining some XP. Whether it’s an intense peace negotiation with a local warlord, a death-defying escape from a collapsing temple complex, or completing a crucial ritual to lift a curse, acts of heroism come in many forms other than stabbing goblins with pointy sticks. 

When your players solve a puzzle, avoid a trap, navigate a social or exploration-based challenge, or anything else that’s risky but doesn’t involve an initiative roll, you can reward them with XP based on the potential ramifications – which you calculate using the table above. 

An easy social encounter in which a group of 3rd level characters bribe their way past a town guard would net them 75 XP. Set that encounter outside an enemy stronghold teeming with hobgoblin warriors, however, and the repercussions get infinitely more deadly.

You may want to consider it a hard social encounter and award the party a juicy 225 XP instead. 

Why (and when) to use XP? 

XP-based Advancement lends itself to a style of play in which the players take greater control over the story. Gaining XP and levels becomes more central to the progression of the game and, because players know how to go about getting XP, they can take a greater hand in deciding how to go about it. 

I like to use XP-based advancement to give games a more old school feel, especially if they’re set in a sandbox-style area where there are wandering monsters, multiple dungeons to explore, a sinister cult or two, and maybe some politics bubbling away in the background. The players can choose how they want to approach the things they find. 

XP-based advancement also tends to tempt players into taking bigger risks, as they can see the direct correlation between their bravery and their character’s power level. 

The two biggest drawbacks of XP-based play are that, from the DM’s perspective, it adds a whole other layer to adventure design if you want to maintain a sense of “balance” and for your players to progress at the rate you want – not to mention the fact that if you have a plot you want to get through, you run the risk of the party ignoring it for two sessions while they charge off into the woods to murder enough bears to finally hit level 4. 

The biggest issue from the players’ perspective is that XP runs the risk of breaking immersion by making you potentially choose between interesting character-driven choices and the “optimal” decision that will result in getting the most XP. 

If the idea of grinding monsters for levels feels antithetical to the type of game you want to play or run, but you still like the idea of a more player-directed campaign, then you might like Milestone Advancement. 

Milestone Advancement: The Middle Ground 

A lot of people tend to confuse Milestone Advancement with Advancement Without XP. 

The assumption tends to be that Milestone Advancement means the DM just dispenses levels when they feel the characters have completed enough game when, in reality, it sits somewhere between this style of play and XP-based leveling. 

Milestone Advancement still uses XP, but instead of drip-feeding it to players after every dead goblin and circumnavigated guard, the DP awards XP based on their own criteria.

These XP triggers can range from completing chunks of an adventure’s plot to exploring a new area, defeating an enemy faction, or any number of other things. 

When done right, Milestone Advancement can be the best way to do both combat/exploration-based games and character-driven stories. 

What Counts as a Milestone? 

A few examples of milestones that could include: 

• Accomplishing one in a series of goals necessary to complete the adventure.
• Discovering a hidden location or piece of information relevant to the adventure.
• Reaching an important destination.
• Overcoming a natural obstacle or hazard. 
• Evading detection by a monster.
• Hauling an unwieldy piece of loot back to town through a wolf-infested forest. 
• Having a moment of genuine character growth.  

Basically, you can approach milestones however you like, making them a useful way to reinforce the focus of your campaign. 

DM’s Tip: This method actually makes the DM treat XP the same way that they would treat awarding Inspiration. Although this can effectively turn your players into a gaggle of hungry cats, constantly turning to you after everything they do to ask “did I get XP for that?” Try to discourage this behavior; if you feed them a juicy 50 XP once because they wouldn’t stop meowing, they’ll never let you hear the end of it. 

Want to run a game about becoming notorious monster hunters? Saving villagers from a griffon, driving off a pack of harpies, successfully tracking a werewolf to its lair, and (of course) slaying a dragon would all be great milestones at which to grant XP. 

Want to run a game in which your players are pirates? Getting their first ship, upgrading it, capturing their first prize, and having a large bounty placed on their heads by the Royal Navy would all be good opportunities for a Milestone. 

When determining how much XP to give out for a milestone, use the difficulty table in the section on XP to compare character level with how challenging or dangerous the milestone was to achieve. 

Advancement Without XP

The method most commonly used by modern dungeon masters. Advancement without XP cuts the process of gaining experience out of the game, placing the decision of whether a character levels up or not in the hands of the dungeon master. 

If your campaign is more story or character-driven, or if your players are more interested in narrative than watching their XP score tick up, simply announcing that the party levels up whenever you feel that they’ve done enough to deserve it – or that enough sessions have gone by – can remove a lot of the headaches associated with this mechanic. 

Granted, it takes the “fun” of working towards the next level away from the players, and can sometimes make the process feel a little perfunctory.

I’m using XP-less advancement in my current campaign. It’s working so far because, both tonally and mechanically, the story has ended up bouncing around a lot.

Sessions have veered between dungeon crawling, political intrigue, heists, and poking weird magical artifacts to find out what they do.

As a result, it’s much easier to break up each “chapter” of the story with a level-up than trying to create an equivalent XP gain between slaying gnoll cultists, starting a small brewery, and spending three in-game weeks exploring a vast underground temple complex.

How Do I Do Session-Based Advancement?  

One way to keep the party’s XP momentum rolling in a game without XP is to use sessions as markers.

The Dungeon Master’s Guide recommends that, when using session-based advancement to gain character levels, a good rate of session-based advancement sees characters reach 2nd level after the first session of play, 3rd level after another session, and 4th level after two more sessions.

Afterward, each two or three subsequent four-hour sessions sees the characters gain an additional level.

Conclusion 

All three of the character advancement methods in D&D 5 have their own merits, and which one works for you can depend on the type of campaign you want to run, what your players are interested in, and whether or not you can be bothered to track XP – or would rather spend your prep time focusing on something else. 

In my experience, XP-based advancement works best for dungeon crawls, exploration, and sandbox-based games that echo the traditional “find dungeon, kill monsters, profit” playstyle found in older editions.

Advancement without XP works best for games in which you want to focus on narrative (both character and plot-driven); and Milestone Advancement can be a little of both, but you get out what you put in. 

Whichever method you choose, just make sure your players are on board with it and that you feel comfortable running it. XP is supposed to be a reward, not a chore.