Context bloat is a real problem — and yes, order matters more than most people realize. Descriptions near the top of the tool list get preferentially selected, especially in long contexts where attention degrades.

Two things I do to fight this:

First, skill scoping per task. Instead of exposing all 20+ skills to every agent, each terminal only sees the 3-5 skills relevant to its current dispatch. The orchestrator decides which skills to load before the agent even starts. Less noise, better selection accuracy.

Second, context rotation to prevent context rot setting in. When an agent's context fills up, the system automatically writes a structured handover, clears the window, and resumes in a fresh context. This is critical because a degraded context doesn't just pick worse tools — it starts ignoring instructions entirely. A fresh context with a good handover outperforms a bloated one every time.

I'm actually testing automatic refresh at 60-70% usage right now — not waiting until the window is nearly full, but rotating early to prevent context rot before it starts. Early results suggest that's the sweet spot: late enough that you've done meaningful work, early enough that the handover quality is still high.

The organic discovery problem you're describing is essentially unsolvable with a flat tool list. The more tools you add, the worse selection gets — it's not linear degradation, it's closer to exponential once you pass ~15-20 tools in context. The only path I've found is hierarchical: a routing layer that narrows the set before the agent sees it.