Problem (one or two sentences)

If I manually compress the context or when the token limit is reached, it seems that rolling back the context using checkpoints BEFORE compressing the context doesn't help. I can't verify this for sure, but the number in the header isn't updating.

If the problem exists, in addition to fixing it, I'd also like to see an automatic checkpoint before context compression, so as not to break the done model's outputs.
This can be used in many scenarios. For example, if a smart model with a 200k window has clogged its context and compressed it, you can roll back before compression, select another model with a larger context, and ask it to do whatever you want, such as write an MD file with the desired things exactly as you want it at that moment, because model has all of chat content.

Context (who is affected and when)

If the model itself decides to compress the context, there's no way to go back, even with checkpoints. You might suddenly discover that the agent's workflow or your prompts were incorrect, and you might want to backtrack a bit, perhaps by modifying the task or going back halfway through the chat, but that's impossible.

Reproduction steps

1. Talk with model in chat, make diffs, create automatic checkpoints etc. Context == 250,000.
2. Compress the context by the button in the header (or wait until model make compression itself), it will be, for example 30,000.
3. Go back to older checkpoints before compression and you'll see that the context is back to 250,000.
4. You might think that everything is ok, the context has been restored, and it’s as if the context compression never happened.
5. Continue the conversation with the model, and you discover that the model immediately starts reading multiple files for some reason, and the context now is 50,000.

Expected result

The context is restored along with the checkpoints.

Actual result

Context remains compressed.

Variations tried (optional)

No response

App Version

3.32.1

API Provider (optional)

None

Model Used (optional)

No response

Roo Code Task Links (optional)

No response

Relevant logs or errors (optional)