diff --git a/src/resources/extensions/sf/state-db.js b/src/resources/extensions/sf/state-db.js
index a40b9cecc..9eaff79e1 100644
--- a/src/resources/extensions/sf/state-db.js
+++ b/src/resources/extensions/sf/state-db.js
@@ -6,7 +6,15 @@ import { existsSync, readdirSync } from "node:fs";
 import { join } from "node:path";
 import { loadFile, parseRequirementCounts, parseSummary } from "./files.js";
 import { findMilestoneIds } from "./milestone-ids.js";
-import { resolveMilestoneFile, resolveSfRootFile, resolveSliceFile, resolveSlicePath, resolveTaskFile, resolveTasksDir } from "./paths.js";
+import {
+	resolveMilestoneFile,
+	resolveSfRootFile,
+	resolveSliceFile,
+	resolveSlicePath,
+	resolveTaskFile,
+	resolveTasksDir,
+} from "./paths.js";
+import { loadQueueOrder, sortByQueueOrder } from "./queue-order.js";
 import {
 	getAllMilestones,
 	getMilestone,
@@ -18,9 +26,6 @@ import {
 	getSliceTasks,
 	isDbAvailable,
 } from "./sf-db.js";
-import { isClosedStatus, isDeferredStatus } from "./status-guards.js";
-import { loadQueueOrder, sortByQueueOrder } from "./queue-order.js";
-import { logWarning } from "./workflow-logger.js";
 import {
 	canonicalMilestonePrefix,
 	extractContextTitle,
@@ -30,6 +35,8 @@ import {
 	readMilestoneValidationVerdict,
 	stripMilestonePrefix,
 } from "./state-shared.js";
+import { isClosedStatus, isDeferredStatus } from "./status-guards.js";
+import { logWarning } from "./workflow-logger.js";
 
 // ─── DB-backed State Derivation ────────────────────────────────────────────
 // isStatusDone replaced by isClosedStatus from status-guards.ts (single source of truth).
@@ -328,6 +335,18 @@ async function handleAllSlicesDone(
 			)
 		: true; // fall back to old behaviour if caller didn't pass slices
 	if (!hasRealWork) {
+		// Route into the pre-planning ladder. The dispatcher decides:
+		//
+		//   no CONTEXT file -> discuss-milestone
+		//   has CONTEXT, no RESEARCH -> research-milestone
+		//   has both -> plan-milestone (which decomposes into real
+		//              slices alongside the existing skipped ones)
+		//
+		// The milestone's vision/PDD is already in the DB (set when
+		// the milestone was created via `sf new-milestone`), so the
+		// planner has the purpose it needs. No operator action
+		// required - autonomous mode will pick it up on the next
+		// dispatch tick.
 		return {
 			activeMilestone,
 			activeSlice: null,
@@ -336,11 +355,13 @@ async function handleAllSlicesDone(
 			recentDecisions: [],
 			blockers: [],
 			nextAction:
-				`No slice on milestone ${activeMilestone.id} carries real work ` +
-				`(every slice is skipped or none were ever planned). Run ` +
-				`reassess-roadmap or close the milestone explicitly via ` +
-				`\`sf headless complete-milestone ${activeMilestone.id}\` if the ` +
-				`work is intentionally deferred.`,
+				`Milestone ${activeMilestone.id} has no slice carrying real ` +
+				`work (every slice is skipped). Route into the pre-planning ` +
+				`ladder so the dispatcher picks discuss/research/plan based ` +
+				`on which artifacts are missing. Use ` +
+				`\`sf headless complete-milestone ${activeMilestone.id}\` ` +
+				`only if you want to intentionally defer the work without ` +
+				`planning it.`,
 			registry,
 			requirements,
 			progress: { milestones: milestoneProgress, slices: sliceProgress },
diff --git a/src/resources/extensions/sf/tests/state-all-skipped-replan.test.mjs b/src/resources/extensions/sf/tests/state-all-skipped-replan.test.mjs
new file mode 100644
index 000000000..5adf40da6
--- /dev/null
+++ b/src/resources/extensions/sf/tests/state-all-skipped-replan.test.mjs
@@ -0,0 +1,150 @@
+/**
+ * deriveState: when every slice on the active milestone was *skipped*
+ * (not completed), route into the pre-planning ladder instead of the
+ * validating-milestone phase.
+ *
+ * Background: the original handleAllSlicesDone branch treated
+ * isStatusDone uniformly - "complete", "done", and "skipped" all
+ * counted as "the milestone has finished its work". That collapsed
+ * the migration-placeholder pattern (skip the stub slice -> milestone
+ * advances to validation) with the genuinely-done case. The fix
+ * differentiates them: zero slices in {complete, done} -> pre-planning
+ * so the dispatcher's discuss -> research -> plan ladder takes over.
+ *
+ * This pins:
+ *   - all-skipped milestone routes to pre-planning, not validating
+ *   - at least one complete/done slice keeps the validating-milestone
+ *     behaviour (no regression for the happy path)
+ *   - the nextAction names the dispatcher path so an operator
+ *     reading the snapshot knows what'll happen autonomously
+ */
+
+import assert from "node:assert/strict";
+import { mkdirSync, mkdtempSync, rmSync } from "node:fs";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { afterEach, test } from "vitest";
+import {
+	closeDatabase,
+	insertMilestone,
+	insertSlice,
+	isDbAvailable,
+	openDatabase,
+} from "../sf-db.js";
+import { deriveState, invalidateStateCache } from "../state.js";
+
+const tmpDirs = [];
+
+afterEach(() => {
+	closeDatabase();
+	if (!isDbAvailable()) {
+		openDatabase(":memory:");
+		closeDatabase();
+	}
+	invalidateStateCache();
+	while (tmpDirs.length > 0) {
+		const dir = tmpDirs.pop();
+		if (dir) rmSync(dir, { recursive: true, force: true });
+	}
+});
+
+function makeProject(milestoneId) {
+	const dir = mkdtempSync(join(tmpdir(), "sf-state-allskipped-"));
+	tmpDirs.push(dir);
+	mkdirSync(join(dir, ".sf", "milestones", milestoneId, "slices", "S01"), {
+		recursive: true,
+	});
+	openDatabase(join(dir, ".sf", "sf.db"));
+	insertMilestone({
+		id: milestoneId,
+		title: "All-skipped milestone",
+		status: "active",
+	});
+	return dir;
+}
+
+test("all_slices_skipped_when_deriving_state_returns_pre_planning", async () => {
+	const dir = makeProject("M501");
+	insertSlice({
+		milestoneId: "M501",
+		id: "S01",
+		title: "Migration placeholder",
+		status: "skipped",
+		sequence: 1,
+	});
+
+	const state = await deriveState(dir);
+
+	assert.equal(state.activeMilestone?.id, "M501");
+	assert.equal(state.phase, "pre-planning");
+	// activeSlice is intentionally null - pre-planning needs the
+	// dispatcher to pick the next unit type from artifacts.
+	assert.equal(state.activeSlice, null);
+	// nextAction must surface the autonomous path so operators know
+	// SF will plan on its own.
+	assert.match(
+		state.nextAction,
+		/pre-planning ladder|discuss\/research\/plan|every slice is skipped/i,
+	);
+});
+
+test("complete_slice_when_deriving_state_returns_validating_milestone", async () => {
+	const dir = makeProject("M502");
+	insertSlice({
+		milestoneId: "M502",
+		id: "S01",
+		title: "Real work",
+		status: "complete",
+		sequence: 1,
+	});
+	insertSlice({
+		milestoneId: "M502",
+		id: "S02",
+		title: "Migration placeholder",
+		status: "skipped",
+		sequence: 2,
+	});
+
+	const state = await deriveState(dir);
+
+	assert.equal(state.activeMilestone?.id, "M502");
+	assert.equal(state.phase, "validating-milestone");
+});
+
+test("done_slice_when_deriving_state_returns_validating_milestone", async () => {
+	const dir = makeProject("M503");
+	insertSlice({
+		milestoneId: "M503",
+		id: "S01",
+		title: "Legacy-style done slice",
+		status: "done",
+		sequence: 1,
+	});
+
+	const state = await deriveState(dir);
+
+	assert.equal(state.activeMilestone?.id, "M503");
+	assert.equal(state.phase, "validating-milestone");
+});
+
+test("multiple_skipped_slices_when_deriving_state_returns_pre_planning", async () => {
+	const dir = makeProject("M504");
+	insertSlice({
+		milestoneId: "M504",
+		id: "S01",
+		title: "First placeholder",
+		status: "skipped",
+		sequence: 1,
+	});
+	insertSlice({
+		milestoneId: "M504",
+		id: "S02",
+		title: "Second placeholder",
+		status: "skipped",
+		sequence: 2,
+	});
+
+	const state = await deriveState(dir);
+
+	assert.equal(state.phase, "pre-planning");
+});