When can you take a rogue dip

[Drizztguen]

I've created a monk and I'm interested in taking a one level rogue dip. When is the best point to take it? The monk gets a nice perk on almost every level, and I'm playing a campaign that will likely get my monk to level 9...

[JellyPooga]

If it were me, I'd look at taking a 2 or 3 level sip from the (possibly poisoned) cup of Roguishness and I'd do it sooner rather than later.

Expertise, Cunning Action and the Rogue Archetype features at Rogue 3 (not to mention the 2nd d6 of Sneak Attack) are all well worth the investment, IMO. I'd, personally, go;

Level 1: Monk - For flavour and better Saving Throw proficiencies.
Level 2-4: Rogue 3 - Tasty, tasty Rogue features.
Level 5+: Monk - Because that's the Class you want to be

[JackPhoenix]

Depend on your concept and how long the campaign should go, but I'd propably wait after you get Extra Attack at level 5

[JellyPooga]

Depend on your concept and how long the campaign should go, but I'd probably wait after you get Extra Attack at level 5

Extra Attack is overrated for Monks and Rogues both.

Monks get a functional, if limited, equivalent at level two with Flurry of Blows and Rogues can only apply Sneak Attack once per turn. Extra Attack can wait.

Delaying your first ASI, Monastic Tradition, Stunning Strike and Ki pool are much more of concern than Extra Attack, IMO.

[Naanomi]

Monk 1/Rogue (2-3)/Monk X is good, though I can see an argument for Monk 3/Rogue (2-3)/Monk X as well (if you are really wanting that subclass feature and flurry)

[treecko]

Extra attack for monk may not be the best, but level 5 is the best level for monk because stunning strike is is only reason to play a monk (mechanically speaking)(EDIT: Actually, there's one more reason and that is mobility, which rogue 2 helps a lot with). While rogue seems tempting, rogue 2 is what you really want for sunning action, although you can get away without it because monk can do all the cunning actions (but with a bit of ki). I would suggest monk 5/rogue 3. Afterwords, it depends on how far you'll think that the campaign will go. The immediate ability score increase is tempting if it won't go much farther, if you are monk levels will pay off in more ki. Taking only 2 rogue levels is also an option, as you may not gain much from the arcehtypes.

What do you hope to gain out of the dip? If it's just skills, a 1 level dip for expertise might be fine, as the monk is one of the only classes with a lot of options for bonus action anyway. In which case, taking one level of rogue won't put you down too much, I recommend either after level 1 or level 5.

[Arkhios]

Extra attack for a rogue is another chance at landing that precious once per turn sneak attack, even for monk/rogue. Flurry of blows is made with unarmed strikes only, and one can't just sneak attack with an unarmed strike.

Plus, Flurry of Blows is bonus action, which competes with a possible two-weapon fighting attack (which, when using appropriate weapon, is also another chance to land a sneak attack)

[Drizztguen]

What do you hope to gain out of the dip? If it's just skills, a 1 level dip for expertise might be fine, as the monk is one of the only classes with a lot of options for bonus action anyway. In which case, taking one level of rogue won't put you down too much, I recommend either after level 1 or level 5.

I was looking more for the extra abilities and expertise. The sneak attack is not as helpful as I initially thought, but I can use it for long bows (my monk is a wood elf) and for Shuriken (darts).

...and the thieves tool proficiency since our party has no thieves.

[Specter]

Take it right away. Expertise and Sneak Attack define your play style early on.

[djreynolds]

Short swords and daggers are monk weapons and finesse, so you can sneak attack with them. And 2d6 extra damage once a turn is very nice.

Rogue gives cunning action which lets you freely disengage as bonus action, yes it competes with FOB and other stuff but it is KI point friendly.

For me the extra attack is insurance.

And you can easily wade into combat with a dagger and throw it at the mook smacking the fighter for a sneak attack, and then press onto the evil wizard and beat him with you fists.

And then, you now also have to skills for expertise, and since you have a high wisdom and dex, stealth and perception seem real good.

And the thief's fast hands, is sweet if you can afford the healer's feat as monk/rogue (possibly not) coupled with your crazy movement, you can get kill in the frontlines and run all the way back to me, the cowering wizard, and bring me back to life after the goblin just killed me with his frying pan.

Its a tough sell, but rogue five is very nice for uncanny dodge. And do not discount, 3 levels of ranger, as hunter's have some good stuff there, spells, and archery style for your bow.

[Arkhios]

Short swords and daggers are monk weapons and finesse, so you can sneak attack with them. And 2d6 extra damage once a turn is very nice.

This. I find it awesome that even the smallest and most unassuming weapons turn into devastating equipment in the hands of a high level monk (Because Martial Arts lets you swap your Martial Arts damage die for the weapon's own, if you want to; eventually you can hit with a dagger and deal damage in d10's).