diff --git a/src/resources/extensions/sf/auto-start.ts b/src/resources/extensions/sf/auto-start.ts
index fd407539e..738988b5b 100644
--- a/src/resources/extensions/sf/auto-start.ts
+++ b/src/resources/extensions/sf/auto-start.ts
@@ -550,8 +550,12 @@ export async function bootstrapAutoSession(
         // Auto mode: autonomously map the codebase and create milestones
         // without waiting for user answers. Uses discuss-headless prompt.
         ctx.ui.notify("No milestones found. Bootstrapping from codebase analysis.", "info");
-        const { dispatchHeadlessBootstrap } = await import("./guided-flow.js");
-        await dispatchHeadlessBootstrap(ctx, pi, base);
+        const { bootstrapNewMilestone, dispatchNewMilestoneDiscuss, injectTodoContext } = await import("./guided-flow.js");
+        const nextId = bootstrapNewMilestone(base);
+        await dispatchNewMilestoneDiscuss(ctx, pi, base, nextId, {
+          auto: true,
+          preamble: injectTodoContext(base, "This is an autonomous session."),
+        });
 
         invalidateAllCaches();
         const postState = await deriveState(base);
@@ -593,8 +597,12 @@ export async function bootstrapAutoSession(
         const hasContext = !!(contextFile && (await loadFile(contextFile)));
         if (!hasContext) {
           ctx.ui.notify(`Milestone ${mid} has no context. Bootstrapping from codebase analysis.`, "info");
-          const { dispatchHeadlessBootstrap } = await import("./guided-flow.js");
-          await dispatchHeadlessBootstrap(ctx, pi, base);
+          const { bootstrapNewMilestone, dispatchNewMilestoneDiscuss, injectTodoContext } = await import("./guided-flow.js");
+          const nextId = bootstrapNewMilestone(base);
+          await dispatchNewMilestoneDiscuss(ctx, pi, base, nextId, {
+            auto: true,
+            preamble: injectTodoContext(base, "This is an autonomous session."),
+          });
 
           invalidateAllCaches();
           const postState = await deriveState(base);
diff --git a/src/resources/extensions/sf/guided-flow.ts b/src/resources/extensions/sf/guided-flow.ts
index e931c430d..31d3c7079 100644
--- a/src/resources/extensions/sf/guided-flow.ts
+++ b/src/resources/extensions/sf/guided-flow.ts
@@ -73,6 +73,30 @@ export {
 } from "./guided-flow-queue.js";
 import { logWarning } from "./workflow-logger.js";
 
+// ─── Todo/Spec File Detection ────────────────────────────────────────────────
+
+const TODO_FILE_NAMES = ["todo.md", "TODO.md", "SPEC.md", "spec.md"];
+
+/**
+ * If a todo/spec file exists at the project root, read and delete it, then
+ * append its contents to `preamble` so any discuss or bootstrap prompt treats
+ * it as the primary specification. Returns the (possibly enriched) preamble.
+ *
+ * Called identically in auto-mode bootstrap and interactive discuss — one flow.
+ */
+export function injectTodoContext(basePath: string, preamble: string): string {
+  for (const fname of TODO_FILE_NAMES) {
+    const fpath = join(basePath, fname);
+    if (!existsSync(fpath)) continue;
+    try {
+      const content = readFileSync(fpath, "utf-8").slice(0, 8000);
+      try { unlinkSync(fpath); } catch { /* non-fatal */ }
+      return `${preamble}\n\n### ${fname} (user-provided specification)\n\n${content}`;
+    } catch { /* non-fatal — fall through */ }
+  }
+  return preamble;
+}
+
 // ─── ID Generation with Reservation ─────────────────────────────────────────
 
 /**
@@ -556,7 +580,7 @@ async function prepareAndBuildDiscussPrompt(
  * Bootstrap a .sf/ project from scratch for headless use.
  * Ensures git repo, .sf/ structure, gitignore, and preferences all exist.
  */
-function bootstrapProject(basePath: string): void {
+export function bootstrapProject(basePath: string): void {
   if (!nativeIsRepo(basePath) || isInheritedRepo(basePath)) {
     const mainBranch = loadEffectiveSFPreferences()?.preferences?.git?.main_branch || "main";
     nativeInit(basePath, mainBranch);
@@ -609,63 +633,69 @@ export async function showHeadlessMilestoneCreation(
 
 
 /**
- * Headless auto-mode bootstrap: dispatch the discuss-headless unit without
- * triggering pendingAutoStartMap (caller is already inside bootstrapAutoSession).
- *
- * Seeds the prompt by auto-reading README.md / package.json / go.mod from the
- * project root so the model can map the codebase and plan autonomously.
+ * Single discuss-dispatch entry point for new milestones.
+ * auto=true  → headless prompt, rootFiles seed, plan-milestone workflow, no pendingAutoStartMap
+ * auto=false → discuss prompt with preparation, discuss-milestone workflow, sets pendingAutoStartMap
  */
-export async function dispatchHeadlessBootstrap(
+export async function dispatchNewMilestoneDiscuss(
   ctx: ExtensionCommandContext,
   pi: ExtensionAPI,
   basePath: string,
-): Promise<string> {
+  nextId: string,
+  options: { auto: boolean; preamble: string; step?: boolean },
+): Promise<void> {
+  if (options.auto) {
+    const seedParts: string[] = [options.preamble, ""];
+    const rootFiles = ["README.md", "README.rst", "package.json", "go.mod", "Cargo.toml", "pyproject.toml"];
+    for (const fname of rootFiles) {
+      try {
+        const fpath = join(basePath, fname);
+        if (existsSync(fpath)) {
+          const content = readFileSync(fpath, "utf-8").slice(0, 4000);
+          seedParts.push(`### ${fname}\n\n${content}`);
+        }
+      } catch { /* non-fatal */ }
+    }
+    seedParts.push(
+      "",
+      [
+        "Autonomously analyze this codebase to plan what needs to be built or improved.",
+        "",
+        "Investigation approach:",
+        "1. Scout the codebase deeply — use rg, find, ast-grep, and file reads to understand structure, patterns, and tech stack",
+        "2. Run existing tests (go test, cargo test, npm test, etc.) to measure current quality",
+        "3. Web search for industry best practices for this type of software — testing strategies, architecture patterns, operational requirements",
+        "4. Research any libraries, frameworks, or external services involved — get current API docs and constraints",
+        "5. Identify gaps: missing tests, incomplete features, error handling, observability, security, documentation",
+        "",
+        "Goal: define milestones that represent the highest-value work to make this software production-ready, well-tested, and complete.",
+        "Use all available models and research tools. Treat your findings as the specification.",
+      ].join("\n"),
+    );
+    const prompt = buildHeadlessDiscussPrompt(nextId, seedParts.join("\n"), basePath);
+    // Do NOT set pendingAutoStartMap — caller (bootstrapAutoSession) manages the loop
+    await dispatchWorkflow(pi, prompt, "sf-run", ctx, "plan-milestone");
+  } else {
+    pendingAutoStartMap.set(basePath, { ctx, pi, basePath, milestoneId: nextId, step: options.step, createdAt: Date.now() });
+    const prompt = await prepareAndBuildDiscussPrompt(ctx, pi, nextId, options.preamble, basePath);
+    await dispatchWorkflow(pi, prompt, "sf-run", ctx, "discuss-milestone");
+  }
+}
+
+/**
+ * Bootstrap a new milestone: ensure .sf/ structure exists, clear stale
+ * reservations, generate + reserve the next milestone ID, and create its
+ * slice directory. Returns the reserved ID.
+ *
+ * Call this before `dispatchNewMilestoneDiscuss` when starting from auto-start.
+ */
+export function bootstrapNewMilestone(basePath: string): string {
   clearReservedMilestoneIds();
   bootstrapProject(basePath);
-
   const existingIds = findMilestoneIds(basePath);
   const prefs = loadEffectiveSFPreferences();
   const nextId = nextMilestoneIdReserved(existingIds, prefs?.preferences?.unique_milestone_ids ?? false);
-
-  const milestoneDir = join(sfRoot(basePath), "milestones", nextId, "slices");
-  mkdirSync(milestoneDir, { recursive: true });
-
-  // Build seed context from project root files
-  const seedParts: string[] = [
-    "This is an autonomous headless session. No specification document was provided.",
-    "",
-  ];
-  const rootFiles = ["README.md", "README.rst", "package.json", "go.mod", "Cargo.toml", "pyproject.toml"];
-  for (const fname of rootFiles) {
-    try {
-      const fpath = join(basePath, fname);
-      if (existsSync(fpath)) {
-        const content = readFileSync(fpath, "utf-8").slice(0, 4000);
-        seedParts.push(`### ${fname}\n\n${content}`);
-      }
-    } catch { /* non-fatal */ }
-  }
-  seedParts.push(
-    "",
-    [
-      "Autonomously analyze this codebase to plan what needs to be built or improved.",
-      "",
-      "Investigation approach:",
-      "1. Scout the codebase deeply — use rg, find, ast-grep, and file reads to understand structure, patterns, and tech stack",
-      "2. Run existing tests (go test, cargo test, npm test, etc.) to measure current quality",
-      "3. Web search for industry best practices for this type of software — testing strategies, architecture patterns, operational requirements",
-      "4. Research any libraries, frameworks, or external services involved — get current API docs and constraints",
-      "5. Identify gaps: missing tests, incomplete features, error handling, observability, security, documentation",
-      "",
-      "Goal: define milestones that represent the highest-value work to make this software production-ready, well-tested, and complete.",
-      "Use all available models and research tools. Treat your findings as the specification.",
-    ].join("\n"),
-  );
-  const seedContext = seedParts.join("\n");
-
-  const prompt = buildHeadlessDiscussPrompt(nextId, seedContext, basePath);
-  // Do NOT set pendingAutoStartMap — caller (bootstrapAutoSession) handles the loop
-  await dispatchWorkflow(pi, prompt, "sf-run", ctx, "plan-milestone");
+  mkdirSync(join(sfRoot(basePath), "milestones", nextId, "slices"), { recursive: true });
   return nextId;
 }
 
@@ -1465,12 +1495,11 @@ export async function showWorkflowEntry(
     const isFirst = milestoneIds.length === 0;
 
     if (isFirst) {
-      // First ever — skip wizard, just ask directly
-      pendingAutoStartMap.set(basePath, { ctx, pi, basePath, milestoneId: nextId, step: stepMode, createdAt: Date.now() });
-      await dispatchWorkflow(pi, await prepareAndBuildDiscussPrompt(ctx, pi, nextId,
-        `New project, milestone ${nextId}. Do NOT read or explore .sf/ — it's empty scaffolding.`,
-        basePath
-      ), "sf-run", ctx, "discuss-milestone");
+      await dispatchNewMilestoneDiscuss(ctx, pi, basePath, nextId, {
+        auto: false,
+        preamble: injectTodoContext(basePath, `New project, milestone ${nextId}. Do NOT read or explore .sf/ — it's empty scaffolding.`),
+        step: stepMode,
+      });
     } else {
       const choice = await showNextAction(ctx, {
         title: "SF — Singularity Forge",
@@ -1487,11 +1516,11 @@ export async function showWorkflowEntry(
       });
 
       if (choice === "new_milestone") {
-        pendingAutoStartMap.set(basePath, { ctx, pi, basePath, milestoneId: nextId, step: stepMode, createdAt: Date.now() });
-        await dispatchWorkflow(pi, await prepareAndBuildDiscussPrompt(ctx, pi, nextId,
-          `New milestone ${nextId}.`,
-          basePath
-        ), "sf-run", ctx, "discuss-milestone");
+        await dispatchNewMilestoneDiscuss(ctx, pi, basePath, nextId, {
+          auto: false,
+          preamble: injectTodoContext(basePath, `New milestone ${nextId}.`),
+          step: stepMode,
+        });
       }
     }
     return;
@@ -1526,11 +1555,11 @@ export async function showWorkflowEntry(
       const uniqueMilestoneIds = !!loadEffectiveSFPreferences()?.preferences?.unique_milestone_ids;
       const nextId = nextMilestoneIdReserved(milestoneIds, uniqueMilestoneIds);
 
-      pendingAutoStartMap.set(basePath, { ctx, pi, basePath, milestoneId: nextId, step: stepMode, createdAt: Date.now() });
-      await dispatchWorkflow(pi, await prepareAndBuildDiscussPrompt(ctx, pi, nextId,
-        `New milestone ${nextId}.`,
-        basePath
-      ), "sf-run", ctx, "discuss-milestone");
+      await dispatchNewMilestoneDiscuss(ctx, pi, basePath, nextId, {
+        auto: false,
+        preamble: injectTodoContext(basePath, `New milestone ${nextId}.`),
+        step: stepMode,
+      });
     } else if (choice === "status") {
       const { fireStatusViaCommand } = await import("./commands.js");
       await fireStatusViaCommand(ctx);