diff --git a/src/resources/extensions/gsd/auto-worktree.ts b/src/resources/extensions/gsd/auto-worktree.ts
index 7dd510d60..e45ae0544 100644
--- a/src/resources/extensions/gsd/auto-worktree.ts
+++ b/src/resources/extensions/gsd/auto-worktree.ts
@@ -54,7 +54,9 @@ export function shouldUseWorktreeIsolation(basePath: string, overridePrefs?: { i
 
   // Legacy detection: check for existing gsd/*/* branches (branch-per-slice pattern)
   try {
-    const output = execSync("git branch --list 'gsd/*/*'", {
+    // Use unquoted glob pattern — single quotes are not interpreted by cmd.exe on Windows,
+    // causing the pattern to match literally instead of as a glob.
+    const output = execSync("git branch --list gsd/*/*", {
       cwd: basePath,
       stdio: ["ignore", "pipe", "pipe"],
       encoding: "utf-8",
diff --git a/src/resources/extensions/gsd/doctor.ts b/src/resources/extensions/gsd/doctor.ts
index 80bf451f1..16cfd4a58 100644
--- a/src/resources/extensions/gsd/doctor.ts
+++ b/src/resources/extensions/gsd/doctor.ts
@@ -1,6 +1,6 @@
 import { execSync } from "node:child_process";
 import { existsSync, mkdirSync } from "node:fs";
-import { join } from "node:path";
+import { join, sep } from "node:path";
 
 import { loadFile, parsePlan, parseRoadmap, parseSummary, saveFile, parseTaskPlanMustHaves, countMustHavesMentionedInSummary } from "./files.js";
 import { resolveMilestoneFile, resolveMilestonePath, resolveSliceFile, resolveSlicePath, resolveTaskFile, resolveTaskFiles, resolveTasksDir, milestonesDir, gsdRoot, relMilestoneFile, relSliceFile, relTaskFile, relSlicePath, relGsdRootFile, resolveGsdRootFile } from "./paths.js";
@@ -511,7 +511,7 @@ async function checkGitHealth(
         if (shouldFix("orphaned_auto_worktree")) {
           // Never remove a worktree matching current working directory
           const cwd = process.cwd();
-          if (wt.path === cwd || cwd.startsWith(wt.path + "/")) {
+          if (wt.path === cwd || cwd.startsWith(wt.path + sep)) {
             fixesApplied.push(`skipped removing worktree at ${wt.path} (is cwd)`);
           } else {
             try {
@@ -527,7 +527,9 @@ async function checkGitHealth(
 
     // ── Stale milestone branches ─────────────────────────────────────────
     try {
-      const branchOutput = execSync("git branch --list 'milestone/*'", { cwd: basePath, stdio: "pipe" }).toString().trim();
+      // Use unquoted glob — single quotes are not interpreted by cmd.exe on Windows,
+      // causing the pattern to match literally instead of as a glob.
+      const branchOutput = execSync("git branch --list milestone/*", { cwd: basePath, stdio: "pipe" }).toString().trim();
       if (branchOutput) {
         const branches = branchOutput.split("\n").map(b => b.trim().replace(/^\*\s*/, "")).filter(Boolean);
         const worktreeBranches = new Set(milestoneWorktrees.map(wt => wt.branch));
diff --git a/src/resources/extensions/gsd/worktree-manager.ts b/src/resources/extensions/gsd/worktree-manager.ts
index 6b08a52bb..6696b7cf8 100644
--- a/src/resources/extensions/gsd/worktree-manager.ts
+++ b/src/resources/extensions/gsd/worktree-manager.ts
@@ -17,7 +17,7 @@
 
 import { existsSync, mkdirSync, realpathSync } from "node:fs";
 import { execSync } from "node:child_process";
-import { join, resolve } from "node:path";
+import { join, resolve, sep } from "node:path";
 
 // ─── Types ─────────────────────────────────────────────────────────────────
 
@@ -213,7 +213,11 @@ export function listWorktrees(basePath: string): WorktreeInfo[] {
 
     const entryPath = wtLine.replace("worktree ", "");
     const branch = branchLine.replace("branch refs/heads/", "");
-    const branchWorktreeName = branch.startsWith("worktree/") ? branch.slice("worktree/".length) : null;
+    const branchWorktreeName = branch.startsWith("worktree/")
+      ? branch.slice("worktree/".length)
+      : branch.startsWith("milestone/")
+        ? branch.slice("milestone/".length)
+        : null;
     const entryVariants = [resolve(entryPath)];
     if (existsSync(entryPath)) {
       entryVariants.push(realpathSync(entryPath));
@@ -272,7 +276,7 @@ export function removeWorktree(
   // If we're inside the worktree, move out first — git can't remove an in-use directory
   const cwd = process.cwd();
   const resolvedCwd = existsSync(cwd) ? realpathSync(cwd) : cwd;
-  if (resolvedCwd === resolvedWtPath || resolvedCwd.startsWith(resolvedWtPath + "/")) {
+  if (resolvedCwd === resolvedWtPath || resolvedCwd.startsWith(resolvedWtPath + sep)) {
     process.chdir(basePath);
   }