diff --git a/src/resources/extensions/gsd/auto.ts b/src/resources/extensions/gsd/auto.ts
index afa824d95..8872863da 100644
--- a/src/resources/extensions/gsd/auto.ts
+++ b/src/resources/extensions/gsd/auto.ts
@@ -725,25 +725,68 @@ export async function startAuto(
     clearLock(base);
   }
 
-  const state = await deriveState(base);
+  let state = await deriveState(base);
 
   // No active work at all — start a new milestone via the discuss flow.
+  // After discussion completes, checkAutoStartAfterDiscuss() (fired from
+  // agent_end) will detect the new CONTEXT.md and restart auto mode.
+  // If the LLM didn't follow the discussion protocol (e.g. started editing
+  // files directly for a simple task), we re-derive state and either proceed
+  // with what was created or notify the user clearly (#609).
   if (!state.activeMilestone || state.phase === "complete") {
     const { showSmartEntry } = await import("./guided-flow.js");
     await showSmartEntry(ctx, pi, base, { step: requestedStepMode });
-    return;
+
+    // Re-derive state after discussion — the LLM may have created artifacts
+    // even if it didn't follow the full protocol.
+    invalidateAllCaches();
+    const postState = await deriveState(base);
+    if (postState.activeMilestone && postState.phase !== "complete" && postState.phase !== "pre-planning") {
+      // Discussion produced enough artifacts to proceed — fall through
+      // to auto mode activation below instead of returning.
+      state = postState;
+    } else if (postState.activeMilestone && postState.phase === "pre-planning") {
+      // Milestone directory exists but no context — check if context was written
+      const contextFile = resolveMilestoneFile(base, postState.activeMilestone.id, "CONTEXT");
+      const hasContext = !!(contextFile && await loadFile(contextFile));
+      if (hasContext) {
+        state = postState;
+        // Fall through — auto mode will research + plan it
+      } else {
+        ctx.ui.notify(
+          "Discussion completed but no milestone context was written. Run /gsd to try the discussion again, or /gsd auto after creating the milestone manually.",
+          "warning",
+        );
+        return;
+      }
+    } else {
+      return;
+    }
   }
 
   // Active milestone exists but has no roadmap — check if context exists.
   // If context was pre-written (multi-milestone planning), auto-mode can
   // research and plan it. If no context either, need user discussion.
   if (state.phase === "pre-planning") {
-    const contextFile = resolveMilestoneFile(base, state.activeMilestone.id, "CONTEXT");
+    const mid = state.activeMilestone!.id;
+    const contextFile = resolveMilestoneFile(base, mid, "CONTEXT");
     const hasContext = !!(contextFile && await loadFile(contextFile));
     if (!hasContext) {
       const { showSmartEntry } = await import("./guided-flow.js");
       await showSmartEntry(ctx, pi, base, { step: requestedStepMode });
-      return;
+
+      // Same re-derive pattern as above
+      invalidateAllCaches();
+      const postState = await deriveState(base);
+      if (postState.activeMilestone && postState.phase !== "pre-planning") {
+        state = postState;
+      } else {
+        ctx.ui.notify(
+          "Discussion completed but milestone context is still missing. Run /gsd to try again.",
+          "warning",
+        );
+        return;
+      }
     }
     // Has context, no roadmap — auto-mode will research + plan it
   }
@@ -846,7 +889,7 @@ export async function startAuto(
   ctx.ui.notify(`${modeLabel} started. ${scopeMsg}`, "info");
 
   // Secrets collection gate — collect pending secrets before first dispatch
-  const mid = state.activeMilestone.id;
+  const mid = state.activeMilestone!.id;
   try {
     const manifestStatus = await getManifestStatus(base, mid);
     if (manifestStatus && manifestStatus.pending.length > 0) {