Problem

Three bugs with chat summarization (compaction) share a single root cause: ReloadMessages was never wired up in the production chatloop.Run() call.

Bug 1: Compaction never fires between steps

The inline compaction guard in chatloop.go requires both Compaction and ReloadMessages to be non-nil:

if opts.Compaction != nil && opts.ReloadMessages != nil {

Since ReloadMessages was only set in tests, inline compaction was dead code in production. Long multi-step turns could blow through the context window.

Bug 2: Compaction only occurs at end of turn

The post-run safety net doesn't check ReloadMessages, so it was the only compaction path that fired:

if !alreadyCompacted && opts.Compaction != nil { // no ReloadMessages check

This meant compaction only happened once, after the entire agent turn finished.

Bug 3: Agent stops after summarization

After post-run compaction, Run() unconditionally returned nil. processChat then set the chat status to waiting (done). The agent never had a chance to continue with its fresh summarized context.

Fix

1. Wire up ReloadMessages in chatd.go: reloads persisted messages from the database and re-applies system prompts (subagent instruction, workspace AGENTS.md).

2. Wrap the step loop in an outer compaction loop: when compaction fires on the model's final step (compactedOnFinalStep), reload messages and continue the outer loop so the agent re-enters with summarized context.

3. Track compactedOnFinalStep to distinguish inline compaction on the last step (needs re-entry) from inline compaction mid-loop followed by more tool-call steps (agent already consumed the compacted context, no re-entry needed).

4. Add maxCompactionRetries = 3 to prevent infinite compaction loops.

Testing

• All 7 existing compaction tests pass unchanged.
• Added PostRunCompactionReEntersStepLoop test: verifies that when a text-only response triggers compaction, the outer loop re-enters and the agent makes a second stream call with fresh context.