[FEATURE] Feature Request: Configurable clarifying questions after auto-compact Labels: enhancement

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

When context auto-compacts, the continuation prompt includes "continue without asking questions." This forces blind continuation even when the compressed summary leaves task state ambiguous—leading to wasted effort on wrong assumptions that require user correction anyway.

Proposed Solution

Add a configuration option to allow clarifying questions after context compression:
json{
"autoCompact": {
"clarifyingQuestions": "none" | "one" | "as-needed"
}
}
Value | Behavior
"none" | Current behavior (default)
"one" | Allow ONE brief clarifying question before proceeding
"as-needed" | Allow clarifying questions when state is ambiguous

Alternative Solutions

Added guidance to project's CLAUDE.md permitting questions when task state is ambiguous. However, this competes with the hardcoded system instruction and doesn't reliably override it.

Priority

High - Significant impact on productivity

Feature Category

Performance and speed

Use Case Example

_No response_

Additional Context

Complex multi-session projects have nuanced state that summaries can't fully capture
One clarifying question costs far less than proceeding incorrectly then backtracking
Opt-in only; default behavior unchanged for users who prefer it