Hi everyone,

In my last session at my table, the thief seemed pretty bored and frustrated.  We had a massive battle and the thief pretty much had to stand on the ramparts (or chose to) and shoot arrows.  He didn't try to come up with creative ways to sneak attack which is a little on him though.  Still, I want to come up with something fun for him to use his thievery skills that doesn't take up too much of the session.  Our previous DM once had an entire session dedicated to one player doing a sneaky mission and it was awful for everyone but that one player.  I definitely don't want to do that.  I do want to have him put those skills to use in fun ways though. 

So I'm asking for help!  What creative things do you do as DM to help make things fun for the thief at your table? 

Are there any specific modules or premade adventures that you know of that did this well?

If you've played a thief (or more generally a rogue), what sessions were most memorable?

Thanks in advance!

As a thief, he has the second story work feature which lets him climb easier. So one neat thing he can do better than other characters is climb onto roofs or ramparts, break line of sight to bonus action hide, then fire an arrow with advantage to sneak attack.

They dont even need advantage to sneak attack if they have an ally within 5 feet of the target.

Make the player aware that there are options and that they can/should look for ways to gain an advantage against foes. Sometimes the players don't know or remember what skills they have available.

I make sure to put things on the campaign for each player class. For rogue it's the usual doors, traps and stealthy stuff. Beyond that it's things in an area the rogue can do during battle to change things. Like sneak behind a few mins engaged with players to close an area that other mobs are coming from. Or stuff like free someone. The list goes on. Just need things for them to do outside of sneak attacks and stuff. So a fair amount of cover for them in a battle area keeps mine happy.

Maybe a heist? Main party has to distract owner / security to open path for rogue. Periodically jump between, decide DC for hiding ECT based on how well the party is doing? (Ex. Party starts a fuss on the main level, rogue hears a 2nd floor guard walk out of position to help on the ground floor.)

As mentioned - rogues need to get creative in using cover and hiding to manufacture advantage for sneak attacks. Beyond that, maybe give them some fun stuff to play with like poisons, acid, oil, alchemist's fire. Maybe (occasionally) give them opportunities to sneak into places and prepare battle areas with tripwires, pit traps, or any other kind of nasty surprises.

Or if they're up on some rampart maybe tell them "you climb up here and find a trebuchet with a big pile of shaped rocks to be used as ammunition." Let them start dropping rocks on people's heads or something. Hit them with a flask of oil and then shoot them with a flaming arrow? All kinds of fun.

Is this the only combat where the player has seemed bored? Is it possible they're not enjoying combat aspects in general, or that particular story point?

I think he just felt like his only option was to shoot his shortbow.  He never tried to hide using a bonus action or sneak and climb around back or anything.  He just overall seemed pretty disinterested in the fight.  I probably could have helped him out but I'm still fairly new at DMing.  I figured since he didn't have a fun time last session that I'd give him more to do for the next one.

The issue is that a lot of people who play rogues, especially the ones who take Thief, are specifically looking for opportunities to do that solo stealth mission thing.  They love that kind of gameplay, they thrive on it, they built their character for it...and DMs never let them have it.

I get it - I DM myself and the idea of setting aside an hour of the session for one guy to indulge in skullduggery while everyone else watches is unconscionable.  Even as a player who adores rogues and other sneaky types, I never ask my DM to let me have more than ten or fifteen minutes of skullduggery at a stretch unless there's a damn good reason otherwise.  Once convinced my DM to let me have a home infiltration segment in Lost Mines of Phandelver that ran an hour and a half, but only after the main session was over and anyone who wanted to could leave and simply hear what we found the next day, the way their character would.  It was amazing, and remains one of my favorite D&D scenes I've ever played, but it's also not a solution for everybody.

What might help you, Kendis, is splitting focus.  Let your thief have his sneaky missions, but don't let them be the only thing happening.  Split the game's camera, as it were, between the thief's high-tension sneakery and whatever the rest of the party is doing.  While Alice the Thief is trying to find the secret documents implicating Count Baddgai in the badger smuggling ring, perhaps the rest of the party is engaging in a noisy diversion somewhere else.  Whenever something really important happens in either plot thread?  "Okay Alice, you reach up with your thieves' tools to try and silently open the door to Count Baddgai's bedroom.  Meanwhile, across town...Bob!  The guards are shouting for you all to stop!  What do you and the rest of Team Hoebeau do?"

it takes practice, and a lot more bookkeeping and organizing on the DM's part, but if you can pull it off then you keep tension singing on both ends of the divide, and each set of players is invested in what the others are doing.  Nobody has to sit and spin for a few hours while someone else plays D&D, but the thief gets a chance to do their thiefy thing and put the skills they built their character to use to the test.