[D&D 5e] A Knife in the Dark: A Rogue’s Handbook, Part II


clutchbone, originally published on the Wizards of the Coast message boards, later republished at En World; I just turned the ratings to something tumblr-friendly. and added some pictures.] [Part II of V]


[Tasoula In The Alley

by Numberslayer]

Full Guide Contents:

  1. [PART I] 


  2. Know Your Role
  3. Ability Scores
  4. Races
  5. [PART II] 


  6. Rogue Class Features
    | Melee vs Ranged, Skills

  7. [PART III]  Roguish Archetypes | Spells
  8. Multiclassing
  9. Feats & Example Builds
  10. Tips, Tricks & Handy Links


  • 😍
    = Very good

  • 😎
    = Good

  • 😐
    = Average

  • 😭
    = Bad

  • 💩
    = Very bad

5. Backgrounds

Aim for two good skills, or one good skill and some nice extras. Note
that if a character gains the same proficiency from two different
sources, you can choose a different one of the same type (ie a skill or
tool). This might make Backgrounds with redundant proficiencies
marginally superior as they basically let you choose whatever skill or
tool you want in exchange*.

*You can create a custom background

as per PHB p125. If so, choose any two skills, any two tools/languages,
any equipment package, and whatever feature appeals to you. I’d
recommend one that gives free food and/or lodgings (eg Entertainer, Folk
Hero, Outlander) or political influence (eg Guild Merchant, Noble,

Player’s Handbook Backgrounds

: Insight, Religion.
Insight is good if you didn’t dump Wis, Religion is bleh, two extra
languages can be a dud or a blessing depending on your campaign or DM,
and the feature is very campaign specific (ie “What do you mean there
isn’t a Temple of Waukeen in this town?”). Take this if you really want
to play an agent of Shar/Tymora/etc for roleplaying.

: Deception, Sleight
of Hand. Two relevant skills, two relevant tools, 55gp worth of swag,
and a fluff item like loaded die or signet ring. Sweet. The feature can
be handy for forging DOA bounties for assassinations or warrants for
search & seizures.

: Deception, Stealth.
Two relevant skills. You already have proficiency in Thieves’ Tools so
choose whatever tool you want to replace it. Criminal Contact could be
useful for “find that guy” type quests or sending warning messages or
something (“the orcs are coming, pass it on”), but I’d bet it’ll more
often than not turn into a DM tool for delivering quests/plot info. Spy
variant can legitimize your activities.


: Acrobatics, Performance. One good skill, one okay
tool kit & an instrument. One free instrument, costume, and 15 gp.
This feature is actually pretty good. Can help advance plot as well as
save money on lodgings. Less good if your DM regularly forgets to
enforce such expenses. The Gladiator

variant swaps the free instrument for an “inexpensive” weapon, but it
doesn’t give you proficiency. So, no free whip proficiency for rogues
unless your DM houserules it.

Folk Hero
: Animal Handling,
Survival. Bleh. Bad skills, bad tools, bad equipment. Only saving grace
is the feature which nets you free safe houses to hide from local
authorities or rivals. Robin Hood fluff is nice for roleplaying.

Keep reading