gsd-pi 2.80.0-dev.2848d9009 → 2.80.0-dev.42bd34838

package/src/resources/extensions/gsd/tests/unit-runtime.test.ts

@@ -5,9 +5,11 @@ import {
   clearUnitRuntimeRecord,
   formatExecuteTaskRecoveryStatus,
   inspectExecuteTaskDurability,
+  isInFlightRuntimePhase,
   readUnitRuntimeRecord,
   writeUnitRuntimeRecord,
 } from "../unit-runtime.ts";
+import { closeDatabase, insertMilestone, insertSlice, insertTask, openDatabase } from "../gsd-db.ts";
 import { clearPathCache } from '../paths.ts';
 import { test } from 'node:test';
 import assert from 'node:assert/strict';
@@ -22,6 +24,12 @@ writeFileSync(
   "utf-8",
 );
 
+console.log("\n=== in-flight runtime phases ===");
+{
+  assert.equal(isInFlightRuntimePhase("crashed"), true, "crashed records remain recoverable");
+  assert.equal(isInFlightRuntimePhase("finalized"), false, "finalized records are terminal");
+}
+
 console.log("\n=== runtime record write/read/update ===");
 {
   const first = writeUnitRuntimeRecord(base, "execute-task", "M100/S02/T09", 1000, { phase: "dispatched" });
@@ -65,6 +73,35 @@ console.log("\n=== runtime record cleanup ===");
   assert.deepStrictEqual(loaded, null, "record removed");
 }
 
+console.log("\n=== execute-task durability trusts closed DB task status ===");
+{
+  const dbBase = mkdtempSync(join(tmpdir(), "gsd-unit-runtime-db-test-"));
+  mkdirSync(join(dbBase, ".gsd", "milestones", "M300", "slices", "S01", "tasks"), { recursive: true });
+  try {
+    openDatabase(join(dbBase, ".gsd", "gsd.db"));
+    insertMilestone({ id: "M300", title: "DB Milestone", status: "active" });
+    insertSlice({ id: "S01", milestoneId: "M300", title: "DB Slice", status: "in_progress" });
+    insertTask({ id: "T01", milestoneId: "M300", sliceId: "S01", title: "DB Task", status: "complete" });
+    writeFileSync(
+      join(dbBase, ".gsd", "milestones", "M300", "slices", "S01", "S01-PLAN.md"),
+      "# S01\n\n## Tasks\n\n- [ ] **T01: DB Task** `est:10m`\n",
+      "utf-8",
+    );
+    writeFileSync(join(dbBase, ".gsd", "STATE.md"), "## Next Action\nExecute T01 for S01: DB task\n", "utf-8");
+
+    const status = await inspectExecuteTaskDurability(dbBase, "M300/S01/T01");
+    assert.ok(status !== null, "db-complete: status exists");
+    assert.equal(status!.dbComplete, true, "db-complete: closed DB status is captured");
+    assert.equal(status!.summaryExists, false, "db-complete: summary can still be missing");
+    assert.equal(status!.taskChecked, false, "db-complete: checkbox can still be unchecked");
+    assert.equal(status!.nextActionAdvanced, false, "db-complete: next action can still point at task");
+    assert.equal(formatExecuteTaskRecoveryStatus(status!), "DB task status is closed");
+  } finally {
+    closeDatabase();
+    rmSync(dbBase, { recursive: true, force: true });
+  }
+}
+
 console.log("\n=== hook unit type sanitization (slash in unitType) ===");
 {
   // Hook units have unitType like "hook/code-review" with a slash

package/src/resources/extensions/gsd/tests/workflow-tool-executors.test.ts

@@ -165,6 +165,9 @@ test("executeMilestoneStatus returns milestone metadata and slice counts", async
     assert.equal(parsed.sliceCount, 1);
     assert.equal(parsed.slices[0].id, "S01");
     assert.equal(parsed.slices[0].taskCounts.pending, 1);
+    assert.equal(result.details.status, "active");
+    assert.equal(result.details.title, "Milestone One");
+    assert.deepEqual(result.details.slices, parsed.slices);
   } finally {
     closeDatabase();
     cleanup(base);

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/tools/context-mode-tool-result.ts

@@ -0,0 +1,25 @@
+// Project/App: GSD-2
+// File Purpose: Shared Context Mode tool result helpers.
+
+export interface ToolExecutionResult {
+  content: Array<{ type: "text"; text: string }>;
+  details: Record<string, unknown>;
+  isError?: boolean;
+}
+
+export type ContextModeToolName = "gsd_exec" | "gsd_exec_search" | "gsd_resume";
+
+export function contextModeDisabledResult(operation: ContextModeToolName): ToolExecutionResult {
+  return {
+    content: [
+      {
+        type: "text",
+        text:
+          `${operation} is disabled by \`context_mode.enabled: false\` in preferences. ` +
+          "Remove that override or set it to true to re-enable Context Mode tools.",
+      },
+    ],
+    details: { operation, error: "context_mode_disabled" },
+    isError: true,
+  };
+}

package/src/resources/extensions/gsd/tools/exec-search-tool.ts

@@ -4,6 +4,8 @@
 // re-discover past runs without re-executing. Read-only; no DB writes.
 
 import { searchExecHistory, type ExecSearchOptions } from "../exec-history.js";
+import { isContextModeEnabled, type ContextModeConfig } from "../preferences-types.js";
+import { contextModeDisabledResult, type ToolExecutionResult } from "./context-mode-tool-result.js";
 
 export interface ExecSearchToolParams {
   query?: string;
@@ -12,16 +14,14 @@ export interface ExecSearchToolParams {
   limit?: number;
 }
 
-export interface ToolExecutionResult {
-  content: Array<{ type: "text"; text: string }>;
-  details: Record<string, unknown>;
-  isError?: boolean;
-}
-
 export function executeExecSearch(
   params: ExecSearchToolParams,
-  opts: { baseDir: string },
+  opts: { baseDir: string; preferences?: { context_mode?: ContextModeConfig } | null },
 ): ToolExecutionResult {
+  if (!isContextModeEnabled(opts.preferences)) {
+    return contextModeDisabledResult("gsd_exec_search");
+  }
+
   const searchOpts: ExecSearchOptions = {
     query: typeof params.query === "string" ? params.query : undefined,
     runtime: params.runtime,

package/src/resources/extensions/gsd/tools/exec-tool.ts

@@ -12,6 +12,7 @@ import {
   type ExecSandboxResult,
 } from "../exec-sandbox.js";
 import { isContextModeEnabled, type ContextModeConfig } from "../preferences-types.js";
+import { contextModeDisabledResult, type ToolExecutionResult } from "./context-mode-tool-result.js";
 
 export interface ExecToolParams {
   runtime: ExecSandboxRequest["runtime"];
@@ -20,17 +21,12 @@ export interface ExecToolParams {
   timeout_ms?: number;
 }
 
-export interface ToolExecutionResult {
-  content: Array<{ type: "text"; text: string }>;
-  details: Record<string, unknown>;
-  isError?: boolean;
-}
-
 export interface ExecToolDeps {
   baseDir: string;
   preferences: { context_mode?: ContextModeConfig } | null;
   /** Optional override for testing. */
   run?: (req: ExecSandboxRequest, opts: ExecSandboxOptions) => Promise<ExecSandboxResult>;
+  env?: NodeJS.ProcessEnv;
   now?: () => Date;
   generateId?: () => string;
 }
@@ -77,21 +73,6 @@ function isEnabled(prefs: ExecToolDeps["preferences"]): boolean {
   return isContextModeEnabled(prefs);
 }
 
-function disabledResult(): ToolExecutionResult {
-  return {
-    content: [
-      {
-        type: "text",
-        text:
-          "gsd_exec is disabled by `context_mode.enabled: false` in preferences. Remove that " +
-          "override (or set it to true) to re-enable sandboxed tool-output execution.",
-      },
-    ],
-    details: { operation: "gsd_exec", error: "context_mode_disabled" },
-    isError: true,
-  };
-}
-
 function paramError(message: string): ToolExecutionResult {
   return {
     content: [{ type: "text", text: `Error: ${message}` }],
@@ -104,7 +85,7 @@ export async function executeGsdExec(
   params: ExecToolParams,
   deps: ExecToolDeps,
 ): Promise<ToolExecutionResult> {
-  if (!isEnabled(deps.preferences)) return disabledResult();
+  if (!isEnabled(deps.preferences)) return contextModeDisabledResult("gsd_exec");
 
   const runtime = params.runtime;
   if (runtime !== "bash" && runtime !== "node" && runtime !== "python") {
@@ -121,7 +102,7 @@ export async function executeGsdExec(
   const opts = buildExecOptions(
     deps.baseDir,
     deps.preferences?.context_mode,
-    { now: deps.now, generateId: deps.generateId },
+    { env: deps.env, now: deps.now, generateId: deps.generateId },
   );
   const run = deps.run ?? runExecSandbox;
 

package/src/resources/extensions/gsd/tools/memory-tools.ts

@@ -308,6 +308,7 @@ function includeSupersededMemories(rankedActive: Memory[]): Memory[] {
         scope: (row["scope"] as string) ?? "project",
         tags,
         structured_fields: structuredFields,
+        last_hit_at: (row["last_hit_at"] as string | null) ?? null,
       };
     });
   } catch {

package/src/resources/extensions/gsd/tools/plan-slice.ts

@@ -18,6 +18,7 @@ import { renderAllProjections } from "../workflow-projections.js";
 import { writeManifest } from "../workflow-manifest.js";
 import { appendEvent } from "../workflow-events.js";
 import { logWarning } from "../workflow-logger.js";
+import { validatePlanningPathScope } from "../planning-path-scope.js";
 
 export interface PlanSliceTaskInput {
   taskId: string;
@@ -141,6 +142,18 @@ export async function handlePlanSlice(
     return { error: `validation failed: ${(err as Error).message}` };
   }
 
+  const pathScopeError = validatePlanningPathScope(
+    basePath,
+    params.tasks.flatMap((task, index) => [
+      { field: `tasks[${index}].files`, values: task.files },
+      { field: `tasks[${index}].inputs`, values: task.inputs },
+      { field: `tasks[${index}].expectedOutput`, values: task.expectedOutput },
+    ]),
+  );
+  if (pathScopeError) {
+    return { error: `validation failed: ${pathScopeError}` };
+  }
+
   // ── Guards + DB writes inside a single transaction (prevents TOCTOU) ───
   // Guards must be inside the transaction so the state they check cannot
   // change between the read and the write (#2723).

package/src/resources/extensions/gsd/tools/plan-task.ts

@@ -8,6 +8,7 @@ import { renderAllProjections } from "../workflow-projections.js";
 import { writeManifest } from "../workflow-manifest.js";
 import { appendEvent } from "../workflow-events.js";
 import { logWarning } from "../workflow-logger.js";
+import { validatePlanningPathScope } from "../planning-path-scope.js";
 
 export interface PlanTaskParams {
   milestoneId: string;
@@ -66,6 +67,15 @@ export async function handlePlanTask(
     return { error: `validation failed: ${(err as Error).message}` };
   }
 
+  const pathScopeError = validatePlanningPathScope(basePath, [
+    { field: "files", values: params.files },
+    { field: "inputs", values: params.inputs },
+    { field: "expectedOutput", values: params.expectedOutput },
+  ]);
+  if (pathScopeError) {
+    return { error: `validation failed: ${pathScopeError}` };
+  }
+
   // ── Guards + DB writes inside a single transaction (prevents TOCTOU) ───
   // Guards must be inside the transaction so the state they check cannot
   // change between the read and the write (#2723).

package/src/resources/extensions/gsd/tools/resume-tool.ts

@@ -3,22 +3,22 @@
 // re-deriving project memory state.
 
 import { readCompactionSnapshot } from "../compaction-snapshot.js";
+import { isContextModeEnabled, type ContextModeConfig } from "../preferences-types.js";
+import { contextModeDisabledResult, type ToolExecutionResult } from "./context-mode-tool-result.js";
 
 export interface ResumeToolParams {
   /** Ignored — reserved for future variant (e.g. dated snapshots). */
   _variant?: string;
 }
 
-export interface ToolExecutionResult {
-  content: Array<{ type: "text"; text: string }>;
-  details: Record<string, unknown>;
-  isError?: boolean;
-}
-
 export function executeResume(
   _params: ResumeToolParams,
-  opts: { baseDir: string },
+  opts: { baseDir: string; preferences?: { context_mode?: ContextModeConfig } | null },
 ): ToolExecutionResult {
+  if (!isContextModeEnabled(opts.preferences)) {
+    return contextModeDisabledResult("gsd_resume");
+  }
+
   const snapshot = readCompactionSnapshot(opts.baseDir);
   if (snapshot == null) {
     return {

package/src/resources/extensions/gsd/tools/workflow-tool-executors.ts

@@ -813,7 +813,7 @@ export async function executeMilestoneStatus(
 
       return {
         content: [{ type: "text", text: JSON.stringify(result, null, 2) }],
-        details: { operation: "milestone_status", milestoneId: milestone.id, sliceCount: slices.length },
+        details: { operation: "milestone_status", ...result },
       };
     });
   } catch (err) {

package/src/resources/extensions/gsd/unit-context-composer.ts

@@ -112,8 +112,22 @@ const CONTEXT_MODE_LANE_LABELS: Record<Exclude<ContextModePolicy, "none">, strin
   docs: "documentation",
 };
 
-const CONTEXT_MODE_GUIDANCE =
-  "Use `gsd_exec` for noisy commands, `gsd_exec_search` before reruns, and `gsd_resume` after compaction or resume.";
+const CONTEXT_MODE_GUIDANCE_BY_LANE: Record<Exclude<ContextModePolicy, "none">, string> = {
+  interview:
+    "Use `gsd_resume` to restore prior discussion, `gsd_exec` for noisy discovery, and `gsd_exec_search` before repeating scans.",
+  research:
+    "Use `gsd_exec` for noisy research scans, `gsd_exec_search` before reruns, and `gsd_resume` to restore prior findings.",
+  planning:
+    "Use `gsd_resume` for planning continuity, `gsd_exec` for noisy checks, and `gsd_exec_search` before rerunning diagnostics.",
+  execution:
+    "Use `gsd_exec` for builds, tests, and diagnostics, `gsd_exec_search` before reruns, and `gsd_resume` after compaction or resume.",
+  verification:
+    "Use `gsd_exec` for verification commands, `gsd_exec_search` to reuse prior evidence, and `gsd_resume` after compaction or resume.",
+  orchestration:
+    "Use `gsd_resume` before resuming orchestration, `gsd_exec_search` to reuse prior runs, and `gsd_exec` for noisy coordination checks.",
+  docs:
+    "Use `gsd_resume` for prior context, `gsd_exec_search` for saved evidence, and `gsd_exec` for noisy doc validation commands.",
+};
 
 /**
  * Render the Context Mode instruction lane for a unit type. Unknown unit
@@ -129,15 +143,16 @@ export function composeContextModeInstructions(
   if (!manifest || manifest.contextMode === "none") return "";
 
   const lane = CONTEXT_MODE_LANE_LABELS[manifest.contextMode];
+  const guidance = CONTEXT_MODE_GUIDANCE_BY_LANE[manifest.contextMode];
   if (opts.renderMode === "nested") {
-    return `Context Mode (${lane} lane): ${CONTEXT_MODE_GUIDANCE}`;
+    return `Context Mode (${lane} lane): ${guidance}`;
   }
 
   return [
     "## Context Mode",
     "",
     `Lane: **${lane} lane**.`,
-    CONTEXT_MODE_GUIDANCE,
+    guidance,
   ].join("\n");
 }
 

package/src/resources/extensions/gsd/unit-runtime.ts

@@ -10,6 +10,8 @@ import {
 } from "./paths.js";
 import { loadFile, parseTaskPlanMustHaves, countMustHavesMentionedInSummary } from "./files.js";
 import { parseUnitId } from "./unit-id.js";
+import { getTask, isDbAvailable, refreshOpenDatabaseFromDisk } from "./gsd-db.js";
+import { isClosedStatus } from "./status-guards.js";
 
 // Per-record advisory lock — prevents read-modify-write races between
 // concurrent writers updating disjoint fields of the same runtime record.
@@ -67,17 +69,32 @@ export type UnitRuntimePhase =
   | "wrapup-warning-sent"
   | "timeout"
   | "finalize-timeout"
+  | "crashed"
   | "recovered"
   | "finalized"
   | "paused"
   | "skipped";
 
+export const IN_FLIGHT_RUNTIME_PHASES: ReadonlySet<UnitRuntimePhase> = new Set([
+  "dispatched",
+  "wrapup-warning-sent",
+  "timeout",
+  "finalize-timeout",
+  "crashed",
+  "paused",
+]);
+
+export function isInFlightRuntimePhase(phase: UnitRuntimePhase): boolean {
+  return IN_FLIGHT_RUNTIME_PHASES.has(phase);
+}
+
 export interface ExecuteTaskRecoveryStatus {
   planPath: string;
   summaryPath: string;
   summaryExists: boolean;
   taskChecked: boolean;
   nextActionAdvanced: boolean;
+  dbComplete: boolean;
   mustHaveCount: number;
   mustHavesMentionedInSummary: number;
 }
@@ -199,6 +216,12 @@ export async function inspectExecuteTaskDurability(
   const escapedTid = tid.replace(/[.*+?^${}()|[\]\\]/g, "\\$&");
   const taskChecked = !!planContent && new RegExp(`^- \\[[xX]\\] \\*\\*${escapedTid}:`, "m").test(planContent);
   const nextActionAdvanced = !new RegExp(`Execute ${tid}\\b`).test(stateContent);
+  let dbComplete = false;
+  if (isDbAvailable()) {
+    refreshOpenDatabaseFromDisk();
+    const task = getTask(mid, sid, tid);
+    dbComplete = !!task && isClosedStatus(task.status);
+  }
 
   // Must-have coverage: load task plan and count mentions in summary
   let mustHaveCount = 0;
@@ -225,12 +248,14 @@ export async function inspectExecuteTaskDurability(
     summaryExists,
     taskChecked,
     nextActionAdvanced,
+    dbComplete,
     mustHaveCount,
     mustHavesMentionedInSummary,
   };
 }
 
 export function formatExecuteTaskRecoveryStatus(status: ExecuteTaskRecoveryStatus): string {
+  if (status.dbComplete) return "DB task status is closed";
   const missing = [] as string[];
   if (!status.summaryExists) missing.push(`summary missing (${status.summaryPath})`);
   if (!status.taskChecked) missing.push(`task checkbox unchecked in ${status.planPath}`);

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) {