gsd-pi 2.80.0-dev.e51d2c88c → 2.80.0-dev.e6c48c3af

package/src/resources/extensions/gsd/tests/auto-wrapup-inflight-guard.test.ts

@@ -3,8 +3,14 @@
 
 import { describe, test } from "node:test";
 import assert from "node:assert/strict";
-import { readFileSync } from "node:fs";
+import { mkdtempSync, mkdirSync, readFileSync, realpathSync, rmSync } from "node:fs";
 import { join } from "node:path";
+import { tmpdir } from "node:os";
+
+import { autoSession } from "../auto-runtime-state.ts";
+import { dispatchHookUnit } from "../auto.ts";
+import { registerHooks } from "../bootstrap/register-hooks.ts";
+import { clearDiscussionFlowState, getPendingGate } from "../bootstrap/write-gate.ts";
 
 const autoTimersPath = join(import.meta.dirname, "..", "auto-timers.ts");
 const autoTimersSrc = readFileSync(autoTimersPath, "utf-8");
@@ -18,6 +24,37 @@ const runUnitSrc = readFileSync(runUnitPath, "utf-8");
 const registerHooksPath = join(import.meta.dirname, "..", "bootstrap", "register-hooks.ts");
 const registerHooksSrc = readFileSync(registerHooksPath, "utf-8");
 
+function makeHookHarness() {
+  const handlers = new Map<string, Array<(event: any, ctx: any) => Promise<any>>>();
+  const pi = {
+    on(name: string, handler: (event: any, ctx: any) => Promise<any>) {
+      const current = handlers.get(name) ?? [];
+      current.push(handler);
+      handlers.set(name, current);
+    },
+  };
+  const ctx = {
+    ui: {
+      notify: () => {},
+      setStatus: () => {},
+      setWidget: () => {},
+    },
+    modelRegistry: {
+      setDisabledModelProviders: () => {},
+    },
+    setCompactionThresholdOverride: () => {},
+  };
+  async function emit(name: string, event: any): Promise<any> {
+    for (const handler of handlers.get(name) ?? []) {
+      const result = await handler(event, ctx);
+      if (result?.block) return result;
+    }
+    return undefined;
+  }
+  registerHooks(pi as any, []);
+  return { emit };
+}
+
 describe("#3512: gsd-auto-wrapup must not interrupt in-flight tool calls", () => {
   test("soft timeout wrapup gates triggerTurn on getInFlightToolCount() === 0", () => {
     // The soft timeout sendMessage must NOT use a hardcoded `triggerTurn: true`.
@@ -73,6 +110,61 @@ describe("#3512: gsd-auto-wrapup must not interrupt in-flight tool calls", () =>
   });
 });
 
+describe("hook dispatch session cwd", () => {
+  test("dispatchHookUnit passes basePath explicitly to newSession", async (t) => {
+    const originalCwd = process.cwd();
+    const basePath = mkdtempSync(join(tmpdir(), "gsd-hook-cwd-"));
+    mkdirSync(join(basePath, ".gsd"), { recursive: true });
+    autoSession.reset();
+    t.after(() => {
+      try {
+        process.chdir(originalCwd);
+      } catch {
+        // best effort cleanup after cwd-sensitive dispatch tests
+      }
+      autoSession.reset();
+      rmSync(basePath, { recursive: true, force: true });
+    });
+
+    let newSessionOptions: unknown;
+    const ctx = {
+      ui: {
+        notify: () => {},
+        setStatus: () => {},
+        setWidget: () => {},
+      },
+      modelRegistry: {
+        getAvailable: () => [],
+      },
+      sessionManager: {
+        getSessionFile: () => join(basePath, "session.jsonl"),
+      },
+      newSession: async (options?: unknown) => {
+        newSessionOptions = options;
+        return { cancelled: false };
+      },
+    };
+    const pi = {
+      sendMessage: () => {},
+      setModel: async () => true,
+    };
+
+    const dispatched = await dispatchHookUnit(
+      ctx as any,
+      pi as any,
+      "review",
+      "execute-task",
+      "M001/S01/T01",
+      "review the completed unit",
+      undefined,
+      basePath,
+    );
+
+    assert.equal(dispatched, true);
+    assert.deepEqual(newSessionOptions, { cwd: basePath });
+  });
+});
+
 describe("#4276: pending/skipped tools stay visible to auto-mode hooks", () => {
   test("tool_call handler marks GSD tools in-flight before execution_start", () => {
     const startMarker = 'pi.on("tool_call", async (event, ctx) => {';
@@ -193,7 +285,7 @@ describe("#4365: tool_execution_start hook must pass toolName to markToolStart",
 });
 
 describe("deep setup approval questions pause immediately", () => {
-  test("register-hooks sets pending gate during message_update without aborting the stream", () => {
+  test("register-hooks defers the pending gate during message_update without aborting the stream", () => {
     const startMarker = 'pi.on("message_update"';
     const endMarker = 'pi.on("session_shutdown"';
     const messageUpdateSection = registerHooksSrc.slice(
@@ -210,8 +302,8 @@ describe("deep setup approval questions pause immediately", () => {
       "message_update must detect approval/question boundaries",
     );
     assert.ok(
-      messageUpdateSection.includes("approvalGateIdForUnit") && messageUpdateSection.includes("setPendingGate"),
-      "plain-text approval questions must set the durable write gate",
+      messageUpdateSection.includes("approvalGateIdForUnit") && messageUpdateSection.includes("deferApprovalGate"),
+      "plain-text approval questions must defer the durable write gate until same-turn draft persistence can finish",
     );
     assert.ok(
       messageUpdateSection.includes("getDiscussionMilestoneIdFor") && messageUpdateSection.includes('"discuss-milestone"'),
@@ -222,4 +314,74 @@ describe("deep setup approval questions pause immediately", () => {
       "message_update must NOT abort the stream — aborting eats the model's question text on external CLI providers; the pending gate set above blocks subsequent tool calls instead",
     );
   });
+
+  test("plain-text approval boundary defers durable gate until same-turn CONTEXT-DRAFT can save", async () => {
+    const base = realpathSync(mkdtempSync(join(tmpdir(), "gsd-deferred-approval-")));
+    const previousCwd = process.cwd();
+    try {
+      mkdirSync(join(base, ".gsd", "milestones", "M003"), { recursive: true });
+      process.chdir(base);
+      clearDiscussionFlowState(base);
+      autoSession.reset();
+      autoSession.basePath = base;
+      autoSession.currentUnit = {
+        type: "discuss-milestone",
+        id: "M003",
+        startedAt: Date.now(),
+      };
+
+      const { emit } = makeHookHarness();
+      await emit("message_update", {
+        message: {
+          role: "assistant",
+          content: [{ type: "text", text: "Did I capture that correctly? If not, tell me what I missed." }],
+        },
+      });
+
+      assert.equal(
+        getPendingGate(base),
+        null,
+        "approval text should not install the durable pending gate until the assistant turn ends",
+      );
+
+      const draftResult = await emit("tool_call", {
+        toolCallId: "draft-save",
+        toolName: "gsd_summary_save",
+        input: {
+          milestone_id: "M003",
+          artifact_type: "CONTEXT-DRAFT",
+          content: "# M003 Draft\n",
+        },
+      });
+      assert.equal(
+        draftResult?.block,
+        undefined,
+        "same-turn CONTEXT-DRAFT persistence should remain allowed after the approval text streams",
+      );
+
+      const finalContextResult = await emit("tool_call", {
+        toolCallId: "final-context",
+        toolName: "gsd_summary_save",
+        input: {
+          milestone_id: "M003",
+          artifact_type: "CONTEXT",
+          content: "# M003 Context\n",
+        },
+      });
+      assert.equal(finalContextResult?.block, true, "final CONTEXT must still wait for approval");
+      assert.match(finalContextResult.reason, /Approval question "depth_verification_M003_confirm"/);
+
+      await emit("agent_end", { messages: [] });
+      assert.equal(
+        getPendingGate(base),
+        "depth_verification_M003_confirm",
+        "agent_end should activate the durable pending gate for the next turn",
+      );
+    } finally {
+      process.chdir(previousCwd);
+      autoSession.reset();
+      clearDiscussionFlowState(base);
+      rmSync(base, { recursive: true, force: true });
+    }
+  });
 });

package/src/resources/extensions/gsd/tests/clean-root-preflight.test.ts

@@ -131,9 +131,11 @@ test("postflightPopStash — restores stashed changes and emits info notificatio
     run('git commit -m "simulate merge"', repo);
 
     const postNotifications: Array<{ msg: string; level: string }> = [];
-    postflightPopStash(repo, "M004", preflight.stashMarker, (msg, level) => {
+    const postflight = postflightPopStash(repo, "M004", preflight.stashMarker, (msg, level) => {
       postNotifications.push({ msg, level });
     });
+    assert.equal(postflight.restored, true, "postflight must report successful restore");
+    assert.equal(postflight.needsManualRecovery, false, "successful restore must not need manual recovery");
 
     // The stashed README.md change must be restored
     const content = readFileSync(join(repo, "README.md"), "utf-8");
@@ -171,7 +173,8 @@ test("preflight + merge + postflight round-trip preserves uncommitted changes",
     run('git commit -m "feat: add feature"', repo);
 
     // Postflight: pop stash
-    postflightPopStash(repo, "M005", preflight.stashMarker, () => {});
+    const postflight = postflightPopStash(repo, "M005", preflight.stashMarker, () => {});
+    assert.equal(postflight.needsManualRecovery, false, "clean restore must not stop auto-mode");
 
     // README.md must still have our local content
     const restored = readFileSync(join(repo, "README.md"), "utf-8");
@@ -197,9 +200,12 @@ test("postflightPopStash conflict warning names the exact stash ref", () => {
     run('git commit -m "simulate conflicting merge"', repo);
 
     const notifications: Array<{ msg: string; level: string }> = [];
-    postflightPopStash(repo, "M005C", preflight.stashMarker, (msg, level) => {
+    const postflight = postflightPopStash(repo, "M005C", preflight.stashMarker, (msg, level) => {
       notifications.push({ msg, level });
     });
+    assert.equal(postflight.restored, false, "conflicted restore must report restored=false");
+    assert.equal(postflight.needsManualRecovery, true, "conflicted restore must require manual recovery");
+    assert.match(postflight.message, /failed after merge of milestone M005C/);
 
     const warning = notifications.find((n) => n.level === "warning")?.msg ?? "";
     assert.match(warning, /git stash pop stash@\{\d+\}/);
@@ -219,7 +225,8 @@ test("postflightPopStash restores the matching GSD stash, not stash@{0}", () =>
     writeFileSync(join(repo, "other.txt"), "other stash\n");
     run('git stash push --include-untracked -m "unrelated newer stash"', repo);
 
-    postflightPopStash(repo, "M006", preflight.stashMarker, () => {});
+    const postflight = postflightPopStash(repo, "M006", preflight.stashMarker, () => {});
+    assert.equal(postflight.needsManualRecovery, false, "targeted restore must not need manual recovery");
 
     const content = readFileSync(join(repo, "README.md"), "utf-8");
     assert.equal(content.replace(/\r\n/g, "\n"), "# target stash\n");
@@ -242,7 +249,8 @@ test("postflightPopStash restores the exact preflight marker when another same-m
     writeFileSync(join(repo, "same-milestone.txt"), "newer same milestone stash\n");
     run('git stash push --include-untracked -m "gsd-preflight-stash [gsd-preflight-stash:M007:other]"', repo);
 
-    postflightPopStash(repo, "M007", preflight.stashMarker, () => {});
+    const postflight = postflightPopStash(repo, "M007", preflight.stashMarker, () => {});
+    assert.equal(postflight.needsManualRecovery, false, "exact marker restore must not need manual recovery");
 
     const content = readFileSync(join(repo, "README.md"), "utf-8");
     assert.equal(content.replace(/\r\n/g, "\n"), "# target stash\n");
@@ -260,7 +268,8 @@ test("postflightPopStash falls back to milestone marker prefix when exact marker
     writeFileSync(join(repo, "README.md"), "# fallback stash\n");
     run('git stash push --include-untracked -m "gsd-preflight-stash [gsd-preflight-stash:M008:fallback]"', repo);
 
-    postflightPopStash(repo, "M008", undefined, () => {});
+    const postflight = postflightPopStash(repo, "M008", undefined, () => {});
+    assert.equal(postflight.needsManualRecovery, false, "fallback marker restore must not need manual recovery");
 
     const content = readFileSync(join(repo, "README.md"), "utf-8");
     assert.equal(content.replace(/\r\n/g, "\n"), "# fallback stash\n");

package/src/resources/extensions/gsd/tests/custom-engine-loop-integration.test.ts

@@ -192,7 +192,11 @@ function makeMockDeps(overrides?: Partial<LoopDeps>): LoopDeps & { callLog: stri
     resolveMilestoneFile: () => null,
     reconcileMergeState: () => "clean",
     preflightCleanRoot: () => ({ stashPushed: false, summary: "" }),
-    postflightPopStash: () => {},
+    postflightPopStash: () => ({
+      restored: true,
+      needsManualRecovery: false,
+      message: "restored",
+    }),
     getLedger: () => null,
     getProjectTotals: () => ({ cost: 0 }),
     formatCost: (c: number) => `$${c.toFixed(2)}`,

package/src/resources/extensions/gsd/tests/integration/git-service.test.ts

@@ -542,6 +542,60 @@ describe('git-service', async () => {
     rmSync(repo, { recursive: true, force: true });
   });
 
+  // Regression: #5500. The LLM occasionally hallucinates files in
+  // task.keyFiles that were never written. Pre-existing scoped-stage code
+  // ran `git add -- <every keyFile>` and failed the entire commit on the
+  // first missing path. Verify that valid paths still commit and missing
+  // ones are dropped silently.
+  test('GitServiceImpl: scoped staging drops missing keyFiles and commits the rest', () => {
+    const repo = initTempRepo();
+    const svc = new GitServiceImpl(repo);
+
+    createFile(repo, "src/index.ts", "export const ok = true;");
+    // Note: src/commands/list.ts is intentionally NOT created — the LLM
+    // claimed it wrote this file but didn't.
+
+    const msg = svc.autoCommit("execute-task", "M001/S01/T02", [], {
+      taskId: "S01/T02",
+      taskTitle: "wire up command list",
+      oneLiner: "Added list command stub",
+      keyFiles: ["src/index.ts", "src/commands/list.ts"],
+    });
+    assert.ok(msg !== null, "autoCommit succeeds when at least one keyFile exists");
+
+    const committed = run("git show --name-only --format= HEAD", repo);
+    assert.ok(committed.includes("src/index.ts"), "existing key file is committed");
+    assert.ok(!committed.includes("src/commands/list.ts"), "missing key file is silently dropped");
+
+    rmSync(repo, { recursive: true, force: true });
+  });
+
+  // Regression: #5500. When ALL keyFiles are bogus, scopedStageTaskFiles
+  // must return false so autoCommit falls back to smartStage. The commit
+  // still goes out (using `git add -A` semantics) instead of failing.
+  test('GitServiceImpl: all missing keyFiles falls back to smartStage', () => {
+    const repo = initTempRepo();
+    const svc = new GitServiceImpl(repo);
+
+    createFile(repo, "src/actually-changed.ts", "export const real = true;");
+
+    const msg = svc.autoCommit("execute-task", "M001/S01/T03", [], {
+      taskId: "S01/T03",
+      taskTitle: "fix path handling",
+      oneLiner: "Hardened path resolution",
+      keyFiles: ["src/wrong/path-1.ts", "src/wrong/path-2.ts"],
+    });
+    assert.ok(msg !== null, "autoCommit falls back to smartStage when all keyFiles are missing");
+
+    const committed = run("git show --name-only --format= HEAD", repo);
+    assert.ok(
+      committed.includes("src/actually-changed.ts"),
+      "smartStage fallback stages real dirty files when scoped staging finds nothing",
+    );
+
+    rmSync(repo, { recursive: true, force: true });
+  });
+
   // ─── GitServiceImpl: empty-after-staging guard ─────────────────────────
 
   test('GitServiceImpl: empty-after-staging guard', () => {

package/src/resources/extensions/gsd/tests/journal-integration.test.ts

@@ -85,7 +85,11 @@ function makeMockDeps(
     resolveMilestoneFile: () => null,
     reconcileMergeState: () => "clean",
     preflightCleanRoot: () => ({ stashPushed: false, summary: "" }),
-    postflightPopStash: () => {},
+    postflightPopStash: () => ({
+      restored: true,
+      needsManualRecovery: false,
+      message: "restored",
+    }),
     getLedger: () => ({ units: [] }),
     getProjectTotals: () => ({ cost: 0 }),
     formatCost: (c: number) => `$${c.toFixed(2)}`,

package/src/resources/extensions/gsd/tests/pre-execution-checks.test.ts

@@ -1,3 +1,6 @@
+// Project/App: GSD-2
+// File Purpose: Unit tests for pre-execution validation checks.
+
 /**
  * pre-execution-checks.test.ts — Unit tests for pre-execution validation checks.
  *
@@ -1542,6 +1545,27 @@ describe("checkFilePathConsistency directory inputs (#4446)", () => {
     assert.equal(results[0].blocking, true);
   });
 
+  test("runtime directory annotation is skipped as a pre-execution file dependency", (t) => {
+    const tempDir = join(tmpdir(), `pre-exec-dir-runtime-${Date.now()}`);
+    mkdirSync(tempDir, { recursive: true });
+    t.after(() => rmSync(tempDir, { recursive: true, force: true }));
+
+    const tasks = [
+      createTask({
+        id: "T02",
+        inputs: ["entries/ directory (runtime)"],
+        expected_output: ["src/commands/delete.ts", "src/index.ts"],
+      }),
+    ];
+
+    const results = checkFilePathConsistency(tasks, tempDir);
+    assert.deepEqual(
+      results,
+      [],
+      "Runtime-only directory inputs are created during command execution, not required before the task starts",
+    );
+  });
+
   test("tilde-prefixed input is matched against $HOME, not the project basePath", (t) => {
     const fakeHome = join(tmpdir(), `pre-exec-tilde-home-${Date.now()}`);
     const projectDir = join(tmpdir(), `pre-exec-tilde-proj-${Date.now()}`);
@@ -1597,6 +1621,20 @@ describe("checkTaskOrdering directory inputs (#4446)", () => {
       "Directory reference should not be treated as reading a file created later",
     );
   });
+
+  test("runtime directory annotation does not produce an ordering violation", () => {
+    const tasks = [
+      createTask({
+        id: "T02",
+        sequence: 0,
+        inputs: ["entries/ directory (runtime)"],
+        expected_output: [],
+      }),
+    ];
+
+    const results = checkTaskOrdering(tasks, "/tmp");
+    assert.deepEqual(results, []);
+  });
 });
 
 // ─── Regression Tests: checkTaskOrdering false positive for pre-execution refs (#4071) ──

package/src/resources/extensions/gsd/tests/worktree-resolver.test.ts

@@ -1,3 +1,5 @@
+// Project/App: GSD-2
+// File Purpose: WorktreeResolver unit and regression tests.
 import test from "node:test";
 import assert from "node:assert/strict";
 import { mkdtempSync, rmSync, mkdirSync, realpathSync } from "node:fs";
@@ -9,6 +11,17 @@ import {
   type NotifyCtx,
 } from "../worktree-resolver.js";
 import { AutoSession } from "../auto/session.js";
+import {
+  closeDatabase,
+  insertMilestone,
+  openDatabase,
+} from "../gsd-db.js";
+import { registerAutoWorker } from "../db/auto-workers.js";
+import {
+  claimMilestoneLease,
+  getMilestoneLease,
+  releaseMilestoneLease,
+} from "../db/milestone-leases.js";
 
 // ─── Helpers ─────────────────────────────────────────────────────────────────
 
@@ -19,11 +32,12 @@ interface CallLog {
 }
 
 function makeSession(
-  overrides?: Partial<{ basePath: string; originalBasePath: string }>,
+  overrides?: Partial<AutoSession>,
 ): AutoSession {
   const s = new AutoSession();
   s.basePath = overrides?.basePath ?? "/project";
   s.originalBasePath = overrides?.originalBasePath ?? "/project";
+  Object.assign(s, overrides);
   return s;
 }
 
@@ -182,6 +196,17 @@ function findCalls(calls: CallLog[], fn: string): CallLog[] {
   return calls.filter((c) => c.fn === fn);
 }
 
+function makeDbBase(): string {
+  const base = mkdtempSync(join(tmpdir(), "gsd-worktree-resolver-"));
+  mkdirSync(join(base, ".gsd"), { recursive: true });
+  return base;
+}
+
+function cleanupDbBase(base: string): void {
+  try { closeDatabase(); } catch { /* noop */ }
+  try { rmSync(base, { recursive: true, force: true }); } catch { /* noop */ }
+}
+
 // ─── Getter Tests ────────────────────────────────────────────────────────────
 
 test("workPath returns s.basePath", () => {
@@ -371,6 +396,43 @@ test("enterMilestone does not create double-nested worktree when originalBasePat
   );
 });
 
+test("enterMilestone reacquires a released same-milestone lease before worktree entry", (t) => {
+  const base = makeDbBase();
+  t.after(() => cleanupDbBase(base));
+  openDatabase(join(base, ".gsd", "gsd.db"));
+  insertMilestone({ id: "M001", title: "Test milestone", status: "active" });
+
+  const workerId = registerAutoWorker({ projectRootRealpath: base });
+  const originalClaim = claimMilestoneLease(workerId, "M001");
+  assert.equal(originalClaim.ok, true);
+  if (!originalClaim.ok) throw new Error("expected test lease claim");
+  assert.equal(releaseMilestoneLease(workerId, "M001", originalClaim.token), true);
+
+  const s = makeSession({
+    basePath: base,
+    originalBasePath: base,
+    workerId,
+    currentMilestoneId: "M001",
+    milestoneLeaseToken: originalClaim.token,
+  });
+  const deps = makeDeps({
+    createAutoWorktree: (basePath: string, milestoneId: string) => join(basePath, ".gsd", "worktrees", milestoneId),
+  });
+  const ctx = makeNotifyCtx();
+  const resolver = new WorktreeResolver(s, deps);
+
+  resolver.enterMilestone("M001", ctx);
+
+  const row = getMilestoneLease("M001");
+  assert.ok(row);
+  assert.equal(row.worker_id, workerId);
+  assert.equal(row.status, "held");
+  assert.equal(row.fencing_token, originalClaim.token + 1);
+  assert.equal(s.milestoneLeaseToken, originalClaim.token + 1);
+  assert.equal(s.basePath, join(base, ".gsd", "worktrees", "M001"));
+  assert.equal(ctx.messages.some((m) => m.level === "error"), false);
+});
+
 // ─── enterMilestone Tests (branch mode) ──────────────────────────────────────
 
 test("enterMilestone in branch mode calls enterBranchModeForMilestone and rebuilds GitService", () => {

package/src/resources/extensions/gsd/worktree-resolver.ts

@@ -25,7 +25,7 @@ import { emitWorktreeCreated, emitWorktreeMerged } from "./worktree-telemetry.js
 import { getCollapseCadence, getMilestoneResquash, resquashMilestoneOnMain } from "./slice-cadence.js";
 import { loadEffectiveGSDPreferences } from "./preferences.js";
 import { resolveWorktreeProjectRoot, normalizeWorktreePathForCompare } from "./worktree-root.js";
-import { claimMilestoneLease, releaseMilestoneLease } from "./db/milestone-leases.js";
+import { claimMilestoneLease, refreshMilestoneLease, releaseMilestoneLease } from "./db/milestone-leases.js";
 
 // ─── Path Comparison Helper ────────────────────────────────────────────────
 /**
@@ -207,23 +207,44 @@ export class WorktreeResolver {
     // milestone (re-entry within the same session).
     if (this.s.workerId) {
       if (this.s.currentMilestoneId === milestoneId && this.s.milestoneLeaseToken !== null) {
-        // Already held — no-op, the heartbeat in loop.ts refreshes TTL.
-      } else {
-        // If we held a different milestone, release it first so other
-        // workers don't have to wait for TTL.
-        if (this.s.currentMilestoneId && this.s.currentMilestoneId !== milestoneId && this.s.milestoneLeaseToken !== null) {
-          try {
-            releaseMilestoneLease(this.s.workerId, this.s.currentMilestoneId, this.s.milestoneLeaseToken);
-          } catch (err) {
-            debugLog("WorktreeResolver", {
-              action: "enterMilestone",
-              milestoneId,
-              releasePriorLeaseError: err instanceof Error ? err.message : String(err),
-            });
-          }
+        const refreshed = refreshMilestoneLease(
+          this.s.workerId,
+          milestoneId,
+          this.s.milestoneLeaseToken,
+        );
+        if (refreshed) {
+          debugLog("WorktreeResolver", {
+            action: "enterMilestone",
+            milestoneId,
+            leaseRefreshed: true,
+            fencingToken: this.s.milestoneLeaseToken,
+          });
+        } else {
+          debugLog("WorktreeResolver", {
+            action: "enterMilestone",
+            milestoneId,
+            staleLeaseToken: this.s.milestoneLeaseToken,
+          });
           this.s.milestoneLeaseToken = null;
         }
+      }
+
+      // If we held a different milestone, release it first so other
+      // workers don't have to wait for TTL.
+      if (this.s.currentMilestoneId && this.s.currentMilestoneId !== milestoneId && this.s.milestoneLeaseToken !== null) {
+        try {
+          releaseMilestoneLease(this.s.workerId, this.s.currentMilestoneId, this.s.milestoneLeaseToken);
+        } catch (err) {
+          debugLog("WorktreeResolver", {
+            action: "enterMilestone",
+            milestoneId,
+            releasePriorLeaseError: err instanceof Error ? err.message : String(err),
+          });
+        }
+        this.s.milestoneLeaseToken = null;
+      }
 
+      if (this.s.milestoneLeaseToken === null) {
         try {
           const claim = claimMilestoneLease(this.s.workerId, milestoneId);
           if (claim.ok) {