Type

Bug

Problem / Value

After manually condensing context and then rewinding/deleting to an earlier user message, the conversation keeps only the very first message and the next new message, losing the expected intervening history. This makes it hard to continue with accurate context after a rewind.

Context

Affects Ask mode workflows where users condense and then correct course by deleting back to a specific turn. Users expect to keep all messages up to the rewind target, dropping only subsequent ones. Instead, only the initial message and the next new message remain.

Reproduction

1. Start Ask mode
2. Send: 'tell me a joke 1' through 'tell me a joke 10'
3. Manually trigger context condensing
4. Send: 'tell me a joke 11'
5. Use the UI to delete/rewind to message 8 ('Delete this and after')
6. Send: 'tell me a joke 12'
7. Observed: Only the initial message and 12+ remain
8. Expected: Keep messages through 8, drop only 9–11

Constraints/Preferences

Avoid losing valid pre-rewind history so users can continue with accurate context after a condense + rewind.