The Chinese had been using large crossbows – akin to Greek and Roman ballistae – for warfare for many of the same reasons that European armies loved them. Their single, large arrow was effectively unstoppable, though this also was rather useless against large groups of infantry unless they were so kind to neatly line up. Old Chinese records mention a special kind of ammunition, called a cup arrow, or ‘storm of crows’, which involves launching many smaller arrows instead of a single large one, a feat that [Tod] really wanted to try and recreate.
In itself this doesn’t sound too complex: just grab some arrows, loosely tie them together in a bundle and slap them on the crossbow. Yet with the immense forces applied on this bundle it clearly turns out that the engineering challenge isn’t quite that straightforward, as the arrows love to scatter wildly in all directions or otherwise be rather unpredictable.
Although we can find historical references to multiple bolt siege crossbows being used, details are sparse on how the Chinese engineers addressed these aforementioned issues, so [Tod] tries a range of approaches to try and make it work on his own siege crossbow. Unfortunately he wasn’t able to make it work reliably, but he says he’ll be back with a range of improvements, with the community invited to pitch in their own ideas.
These type of weapons were very commonly used in China and surrounding nations from hundreds of years BCE to around the 16th century CE, when black powder was used to launch projectiles like fire arrows from a Huo Che or the Korean equivalent of the Hwacha, effectively multiple rocket launchers, not unlike the MLRS units seen in militaries today.

Really highlights how much frustrating fiddling and experimentation is required to keep an odd projectile from keyholing
Medieval siege weapons…truly what I was destined to work on, if I was born in the 1200s
Of course if scurvy or tetanus wouldn’t have taken me first.
Fun fact:
engineer(n.)
mid-14c., enginour, “constructor of military engines,” from Old French engigneor “engineer, architect, maker of war-engines; schemer” (12c.), from Late Latin ingeniare (see engine).
I think the problems are weight of the sabot (cup) and the arrows. The sabot is too heavy, the arrows too light. It means that drag will affect the arrows more than the sabot, and so the sabot kind of ‘pushes’ the arrows out of it’s way in the first few meters. What if you make it so that the sabot doesn’t exit the bow but stays behind? Could be a simple as a rope.
Seems like you could cut a ton of weight, make it out of paper or idunno cane reeds, and have it go up over more of the length of the arrows. Heck just design a scaled-up shotgun shell wad