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Feature Request: Plan status indicators (badge/symbol) on session list items #3969

Description

@RockNoggin

Describe the feature or problem you'd like to solve

When managing multiple sessions, there's no visual way to tell at a glance what stage each session's plan is in. You have to open each session to check progress, which breaks flow when juggling several workstreams.

Proposed solution

Add a small status indicator (symbol with tooltip, or badge) on each session item in the sidebar that reflects the current plan state:

Status Meaning Suggested Icon
Planning Agent is actively generating/refining the plan 🔄 or spinner
PlanReady Plan has been generated and is awaiting user approval or kickoff 📋 or checkmark-outline
PlanInProgress Plan has been approved and work is underway ⚙️ or progress indicator
PlanComplete All plan steps are done ✅ or filled checkmark

Requirements:

  • The indicator should be compact enough to not clutter the session list
  • A tooltip on hover should show the full status label (e.g., "Plan In Progress")
  • Status should update in real-time as the session progresses
  • Sessions without a plan (e.g., chat sessions, sessions in interactive/autopilot mode) can omit the indicator or show a neutral state

Example prompts or workflows

  1. User has 5 project sessions open
  2. Glancing at the sidebar, they can immediately see:
    • Session A: ✅ (done, ready to review/merge)
    • Session B: ⚙️ (agent is executing the plan)
    • Session C: 📋 (plan ready, waiting for approval)
    • Session D: 🔄 (still planning)
  3. User clicks Session C to approve the plan, then moves on — no wasted context-switching

Additional context

Related to #981 (Status Sidebar). This is a lighter-weight version focused specifically on plan lifecycle visibility in the existing session list UI.

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