[FEATURE] Better compact suggestions

Preflight Checklist

• [x] I have searched existing requests and this feature hasn't been requested yet
• [x] This is a single feature request (not multiple features)

Problem Statement

Often when Claude auto compacts the conversation it will continue working roughly on what we were doing, but not correctly most of the times. Compacting is for sure better than starting a whole new conversation, but I feel like it could be a bit "smarter" to seamlesly continue the conversation

Proposed Solution

So I thought about a few different options (without having knowledge about how the compacting actually works)

1. Continuously compact the oldest part of the conversation to always keep let's say 50%~ uncompacted.

1. Compact like normal, but along the conversation add "checkpoints" as to where the context of the tasks changes. Keep these checkpoints in mind when compacting and avoid compacting the latest checkpoint down to latest message to retain 100% context.

Example: I work on my index.html for a moment, then would like to switch to another html file to start working on something else. This creates a checkpoint when we start working on the new page.

Alternative Solutions

_No response_

Priority

Medium - Would be very helpful

Feature Category

API and model interactions

Use Case Example

_No response_

Additional Context

I am terrible at explaining things and especially using coding terminology, so feel free to ask me to explain things in a different way. I won't get offended.