What Happens When I Level Up – Rogue (D&D 5e)

This guide only presents the Traits, Feats, and additional Abilities that your character will acquire when they gain a level. The character progression is broken down per level to facilitate the tracking of incremental changes that can be made for a character. This is to help avoid repeatedly jumping through different sections of the Player’s Handbook every time an additional level is gained.

Before using this guide, please take note of any and all applicable feats, racial traits or background bonuses that your character might gain before choosing a class. Most of these are one time numerical bonuses to Ability Scores or are persistent abilities that your character can use all throughout their adventuring life. Traits/bonuses/features gained by Arcane Tricksters are marked with AT Only.

The Rogue Class Advancement Table

Rogue New
A lot of these are Urchins. Higher res image here.

General notes on Rogues:

  • Rogues typically start with humble daggers as weapons. These short metal implements seem unimpressive with their 1d4 damage roll, but well timed sneak attacks and advantage rolls stack like crazy. When tuned right, this class has the potential to steamroll through challenge appropriate encounters.
  • As a Rogue, you will be the one counted on to deal with locks and sneaky reconnaissance. Whereas the Bard is expected to interact with NPCs, you will be expected to convince doors and chests to open.
  • Rogues with the Arcane Trickster Archetype gradually acquire additional spells and spell slots through level advancement just like regular spellcasters. Whenever you gain a level as an Arcane Trickster, you can replace a current spell with any Enchantment or Illusion spell from the Wizard spell list. This magic school limitation does not apply to spells gained at 8th, 14th, and 20th level.

Roguish Archetypes

*Featured in expansions, homebrew material and Unearthed Arcana. Ask your DM for permission if they’ll allow the use of these Archetypes for your campaign. These options may have additional requirements and/or special features/bonuses when chosen.

Character Advancement – Gaining Levels

1st Level Rogue

  • Initial HP = 8 + Constitution (CON) Modifier
  • Armor Proficiency: Light Armor
  • Weapon Proficiency: Simple Weapons, Hand Crossbows, Longswords, Rapiers, and Shortswords
  • Tool Proficiency: Thieves’ Tools
  • One (1) 1d8 Hit Die
  • +2 Proficiency Bonus
  • Proficiency Bonus added to DEX and INT saving throws
  • Choice of Proficiency Bonus to Acrobatics, Athletics, Deception, Insight, Intimidation, Investigation, Perception, Performance, Persuasion, Sleight of Hand, and Stealth (Choose four)
  • Expertise
  • Sneak Attack (1d6)
  • Thieves’ Cant

2nd Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Cunning Action

3rd Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Roguish Archetype
  • Sneak Attack Damage increased to 2d6

AT Only

  • Three (3) cantrips from the Wizard spell list
  • Three (3) 1st level Enchantment or Illusion spells from the Wizard spell list
  • Two (2) 1st level spell slots

4th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Ability Score improvement (additional 2 points for one ability or 1 point for two abilities) OR a Feat of your choice

AT Only

  • One (1) additional 1st level Enchantment or Illusion spell from the Wizard spell list
  • One (1) additional 1st level spell slot

5th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Uncanny Dodge
  • Sneak Attack Damage increased to 3d6
  • Proficiency Bonus is increased by 1

6th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Expertise II

7th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Evasion
  • Sneak Attack Damage increased to 4d6

AT Only

  • One (1) additional 1st – 2nd level Enchantment or Illusion spell from the Wizard spell list
  • One (1) additional 1st level spell slot
  • Two (2) 2nd level spell slots

8th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Ability Score Improvement OR a Feat of your choice

AT Only

  • One (1) additional 1st – 2nd level spell (any school) from the Wizard spell list

9th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • New Roguish Archetype Feature
  • Sneak Attack Damage increased to 5d6
  • Proficiency Bonus is increased by 1

10th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Ability Score Improvement OR a Feat of your choice

AT Only

  • One (1) additional 1st – 2nd level Enchantment or Illusion spell from the Wizard spell list
  • One (1) additional cantrip from the Wizard spell list
  • One (1) additional 2nd level spell slot

11th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Reliable Talent
  • Sneak Attack Damage increased to 6d6

AT Only

  • One (1) additional 1st – 2nd level Enchantment or Illusion spell from the Wizard spell list

12th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Ability Score Improvement OR a Feat of your choice

13th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • New Roguish Archetype Feature
  • Sneak Attack Damage increased to 7d6
  • Proficiency Bonus is increased by 1

AT Only

  • One (1) additional 1st – 3rd level Enchantment or Illusion spell from the Wizard spell list
  • Two (2) 3rd level spell slots

14th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Blindsense

AT Only

  • One (1) additional 1st – 3nd level spell (any school) from the Wizard spell list

15th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Sneak Attack Damage increased to 8d6
  • Slippery Mind

16th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Ability Score Improvement OR a Feat of your choice

AT Only

  • One (1) additional 1st – 3nd level Enchantment or Illusion spell from the Wizard spell list
  • One (1) additional 3rd level spell slot

17th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • New Roguish Archetype Feature
  • Sneak Attack Damage increased to 9d6
  • Proficiency Bonus is increased by 1

18th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Elusive

19th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Sneak Attack Damage increased to 10d6
  • Ability Score Improvement OR a Feat of your choice

AT Only

  • One (1) additional 1st – 4th level Enchantment or Illusion spell from the Wizard spell list
  • One (1) 4th level spell slot

20th Level Rogue

  • Max HP increase. Add 1d8 + CON Modifier to the current total Max HP
  • One (1) additional 1d8 Hit Die
  • Stroke of Luck

AT Only

  • One (1) additional 1st – 4th level spell (any school) from the Wizard spell list

Given the Rogue skill set progression, it can be hard to avoid playing the typical dark and brooding edgelord. Just make sure to regulate shenanigans and avoid direct party griefing. Too much stolen rations and “missing” magic items and they might become more inclined to turn you over to the town guard.

Please take note of all ability score and bonus increases as your Rogue gains levels and experience. These changes must be properly reflected on your character sheet to show improvements for character statistics like skill checks and attack rolls. Make sure to update the character’s armor class, hit points, bonus initiative, passive perception and other skills that they are proficient with whenever any relevant changes allow you to do so.

For additional information on Roguish Archetypes and the features they grant, refer to resources like the Player’s Handbook, Xanathar’s Guide to Everything or expansion and online material like the ones from Roll20 or The DnD 5e Wikidot website.

– D

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