My understanding of caching with most models/providers is that a prefix substring of the context has to be reused for a cache hit, but not necessarily the whole entire context window. So if you prune tool calls from the history, you're going to get one cache miss on the newly-pruned history, and then you're going to be getting cache hits on every subsequent turn, with a lower number of input tokens. If you prune subsequent tool calls after that, you would still get a cache hit for the already-pruned portion of the context, just not the full context.

So it makes sense to first send stable prompt, reasoning and files content, tool calls summary and actual tool calls at the very end?