It's really weird to me how completely disconnected the main level-up options in the Dungeon Master's Guide are.
Here's the text from 2014 DMG about leveling up your characters based on how many sessions you'd played:
A good rate of session-based advancement is to have characters reach 2nd level after the first session of play, 3rd level after another session, and 4th level after two more sessions. Then spend two or three sessions for each subsequent level. This rate mirrors the standard rate of advancement, assuming sessions are about four hours long.
The 2024 DMG adds a couple little sentences about adjusting this for length of session and accomplishment, but sticks to the general formula above.
So how does that compare to XP gained from combat encounters, which I will note is the default system that the game largely assumes you are using, and which the various rulebooks (2014 and 2024 DMGs, and also Xanathar's Guide To Everything) spend a lot of time and word count (and math) hashing and rehashing.
I'd say that if you're tracking XP by combat it will take you at least 2, and more likely 3 sessions to get to level 2. I've also seen it take a lot more than that, especially with cautious players, or with those still learning the system or playing a new class for the first time.
I'm not saying it's in any way a problem that the recommended progression rate for leveling-up by session is two to three times the speed of advancement if you did the XP math, but it is odd to me that this wide a gap exists without them mentioning it in any of the books that present that math.
Supporting XP math and book references can be found below the fold, along with a fair amount of rambling.
2014 Dungeon Master's Guide:
In the DMG, they tell you that for a first level party, you should aim for about 300 XP worth of encounters (monsters) per player per adventuring day. 300 XP is the amount you need to go from level one to level two, so I can see why that felt to the author like it could roughly jive with leveling up to 2nd level after one session of play.
But they also say in that same section that a party should have 6 to 8 encounters per adventuring day, and take 2 short rests somewhere between them. And they say elsewhere that a typical play session is about 4 hours, and you may have to adjust your level-up speed if your sessions are shorter or longer. I have never found a play group that could get through 6 to 8 encounters of D&D in 4 hours, not even at 1st level where your number of attacks / actions / spell slots per character are at their lowest, and your limited options reduce analysis-paralysis.
I'd say two encounters is more typical (especially with new players or a newly assembled group where everyone's getting to know their characters) but four is doable if the fights are on the easier side and the players don't get sidetracked too much. 1st level fights can potentially be really short and fast, but that's because if anyone gets hit, they're probably KO'd. 6 micro-fights in a session, if the players know their characters well, work together as a team, and don't have many rules questions? That's possible, also assuming the GM has prepped well, but I wouldn't expect it to be the typical or default situation.
The 2014 DMG has four tiers of encounters: Easy, Medium, Hard, and Deadly.
A Deadly Encounter for a 1st level party is 100 XP per player. So you'd need three such Deadly Encounters to reach the 300 XP per player required to level up the first time. Prevailing wisdom is that Challenge Rating in the 2014 books is completely out of whack with reality... but at low level the "medium" fights tend to be too hard (and then at high level they become laughably easy). So having 3 "Deadly" fights in your first session's probably not going to end well. That's three fights where the PCs are outnumbered 2-to-1 by Goblins, or are facing 1 Orc per PC. A random Orc who rolls a crit is very likely to one-shot any 1st-level PC.
After that first Deadly fight, the PCs are likely to really need their Short Rest, and then once they've spent that single Hit Die at least half the party won't see any benefit out of taking the second Short Rest after the 2nd or 3rd fight because they can't heal anyway. So they'll slow down, and/or become more cautious, and/or get TPK'd.
Six "Medium Encounters" (earning 50 XP per PC) is far more doable and less likely to end in a TPK, but again you'd be hard pressed to fit those into a single session. So if you're counting individual XP by encounter budget, that's probably your first level-up happens after 2 or 3 sessions.
Xanathar's Guide To Everything:
If you use the recommended Encounter tables from Xanathar's Guide, you're going to end up with even less XP per PC at low levels than the "Medium Encounters" of the DMG gave, as they recommend that you use one Orc (or other CR 1/2 monster) per 3 PCs. That's going to get you about 33 XP per PC, so it will take 9 or more encounters at that difficulty to get you from 1st to 2nd level.
Xanathar's pointed you towards slightly fewer monsters at 1st level because they understood that first level characters are really vulnerable, and your life-saving options are very limited.
2024 Dungeon Master's Guide:
The four encounter levels of 2014 are restructured and streamlined in the 2024 DMG. The switched to just three levels: Low, Moderate and High Difficulty. The old easy is just gone. For 1st Level characters, the new Low matches the old Medium. The new Moderate matches the old Hard. The new High matches the old Deadly.
At higher level, it actual exceeds those old thresholds completely. For example: in 2014 a challenge for 20th Level PCs was 2,800 XP at Easy / 5,700 XP Medium / 8,500 XP Hard / 12,700 XP Deadly. In 2024 edition that is upped to 6,400 at Low / 13,200 at Moderate / 22,000 at High. So the new lowest level is 12% nastier than the medium level of the old version. And the new High is 73% bigger than the old Deadly. At high levels, that seems sensible to me. I haven't GM'd much high level, but the idea that my PCs in the late stages of a campaign could handle a good bit more than "Deadly" seems very true.
At the lowest level, though, 2014 CR seemed okay-ish. I'm not entirely convinced that early play really needed for 75 XP per PC to be the default encounter for 1st Level heroes. That's just 3 Orcs or 6 Goblins vs a Party of 4 PCs, so I wouldn't say it's necessarily wrong or a mistake, either. It's certainly doable, but I think the PCs will definitely be looking at that Short Rest after the first fight. You probably shouldn't expect them to want to do this four times in a single day, and again it would be hard to compress it into a four hour session without the players feeling a little rushed, and thus increasing the danger of player mistakes leading to PC death.
Worse For Smaller Parties
When I was starting my recent solitaire campaign that I play when insomnia strikes, I was routinely having my 1st Level PC get the snot kicked out of him by lone CR 1/4 (50 XP) enemies, or worse, pairs of CR 1/8 (25 XP each) foes. After the second contrived "this is how he survives" scenario, I introduced a sidekick to back him up, but it was still pretty dicey. Whichever side got the first hit in would usually KO their target, and then gang-up to steamroll the other side. That last bit is maybe less of a danger with 4 PCs, but it's definitely a throttle in early play.
"That was a close one, but I killed both Xvarts, with 2 HP left. Well, time to leave the dungeon and head home to spend my hard-earned 6d6 copper pieces!"
I believe it took that Druid 7 fights to get to 2nd level, and he was KO'd 3 times along the way (and twice had to heal his Ranger sidekick when they were KO'd).
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