You could borrow hero points from Pathfinder. Basically, each player gets one or two hero points at the beginning of the session and can spend it to reroll a d20 at any point in the night. You take the rerolled result. Note that these expire at the end of the session and cannot be stacked up for next time.
Give them custom weapons or spells that are most effective when you roll low.
Out of all the ideas here, this is one that interest me the most. I've seen a lot of things, but not something that does better when you're low...
You might consider adding a puzzle element to encounters that can lower the effective difficulty with clever maneuvers or strategies.
As an example, fighting in a room with a big chandelier overhead. A player can cut the chandelier at the opportune moment to pin a major adversary, allowing them to coup de grace or simply flaunt their victory to the villain's face.
Or perhaps fighting in a room full of mirrors that allow a clever player to reflect a gaze attack. Or doing Battleship style combat, where you have to pick the square of a hidden enemy, but you guarantee a hit if you guess correctly.
In general, try introducing non-dice resolutions to the scene - guessing a magic word that disables a key piece of enemy tech, baiting enemies into an area or formation before springing a trap, completing a ritual that can summon a powerful ally by solving a rubric cube.
If all else fails, you can drop some nice loot them. Awand of fireballs or Staff of the Sun or similar high powered magic item, for instance. Doesn't matter how you roll with these, you're going to have some fun.
Tactical gameplay is already something I very much encourage. One nice thing about playing with the same group for a long time is that I know they'll respond when I put things on the map - opportunities to flank, drop or collapse things, and so on.
Use digital dice?
Narrative solution would be to reveal the party has been cursed somehow this entire time. You can then give them a trinket/spell that mitigates low rolls. They get the best of 2 rolls once per combat or something like that.
We're all experienced players, and it's a digital platform
Don't know if you caught it in the OP, but this is already a digital platform. I will look into the idea of a "trinket of luck" or something (non-attuned, because punishing them for their bad luck seems like a bad move).
Computers can't do random. They usually approximate random by truncating seconds since epoc and throwing them into an algorithm the hashes them up into something that's sort of random. Problem is that time is not really random. You ever notice that your random music shuffle seems to play the same shit all the time? Unless of course somebody else is there to listen, then it plays crazy shit you've never heard before. It probably has less to do with luck and more to do with you having regular listening habits, and the times that it plays crazy shit is those times that you are listening outside of your normal habits. And then there's the algorithm that they use. There's been a number of digital games that I have stopped playing because the "randomizer" was so shit that I could begin to "predict" future rolls.
The luck system might be something to look into. It can help mitigate consecutive failures while maintaining balance.
Thanks for that link! I'll toss that at my group and see what they think.
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