diff --git a/packages/server/src/server/workspace-create-worktree-source.e2e.test.ts b/packages/server/src/server/workspace-create-worktree-source.e2e.test.ts
index fc9efe1684..cd9ec71d83 100644
--- a/packages/server/src/server/workspace-create-worktree-source.e2e.test.ts
+++ b/packages/server/src/server/workspace-create-worktree-source.e2e.test.ts
@@ -493,6 +493,7 @@ async function createRestorableWorkspace(baseRef: string) {
   commitFile(cwd, "feature.txt", "feature change\n");
   const head = runGit(cwd, "rev-parse", "HEAD");
   await client.checkoutRefresh(cwd);
+  expect(await client.getCheckoutStatus(cwd)).toMatchObject({ isPaseoOwnedWorktree: true });
   const before = await client.getCheckoutDiff(cwd, { mode: "base", baseRef: "main" });
   expect(before.error).toBeNull();
   expect(before.files.map((file) => file.path)).toEqual(["feature.txt"]);
diff --git a/packages/server/src/utils/worktree.test.ts b/packages/server/src/utils/worktree.test.ts
index 848feddf99..605e2b8c20 100644
--- a/packages/server/src/utils/worktree.test.ts
+++ b/packages/server/src/utils/worktree.test.ts
@@ -5,6 +5,7 @@ import {
   deletePaseoWorktree,
   isPaseoOwnedWorktreeCwd,
   mapWorkspaceCwdToWorktree,
+  runWorktreeTeardownCommands,
   slugify,
   type CreateWorktreeOptions,
   type WorktreeConfig,
@@ -172,6 +173,14 @@ describe("paseo worktree manager", () => {
 
     const ownership = await isPaseoOwnedWorktreeCwd(created.worktreePath, { paseoHome });
     expect(ownership).toMatchObject({ allowed: true, worktreePath: created.worktreePath });
+    // Windows may report the same root through native 8.3 and JS long spellings.
+    const nativeWorktreePath = realpathSync.native(created.worktreePath);
+    await expect(
+      runWorktreeTeardownCommands({
+        worktreePath: created.worktreePath,
+        teardownCwd: nativeWorktreePath,
+      }),
+    ).resolves.toEqual([]);
     await expect(
       isPaseoOwnedWorktreeCwd(join(created.worktreePath, "packages", "app"), { paseoHome }),
     ).resolves.toMatchObject({
diff --git a/packages/server/src/utils/worktree.ts b/packages/server/src/utils/worktree.ts
index 687f8c1e54..faa7ec4065 100644
--- a/packages/server/src/utils/worktree.ts
+++ b/packages/server/src/utils/worktree.ts
@@ -6,6 +6,7 @@ import { join, basename, dirname, isAbsolute, resolve, sep } from "path";
 import net from "node:net";
 import { createHash } from "node:crypto";
 import stripAnsi from "strip-ansi";
+import pLimit from "p-limit";
 import {
   buildStringCommandShellInvocation,
   createStringCommandShellEnv,
@@ -912,20 +913,32 @@ export function mapWorkspaceRelativeCwdToWorktree(input: {
 // Keep the former realpathSync spelling on Windows: promises.realpath uses the
 // native resolver and can return an 8.3 alias instead of the long path.
 const resolveOwnershipPath = promisify(realpath);
+const resolveNativeOwnershipPath = promisify(realpath.native);
+const ownershipIdentityIo = pLimit(2);
 
 async function normalizePathForOwnership(input: string): Promise<string> {
   try {
-    return await resolveOwnershipPath(input);
+    return await ownershipIdentityIo(() => resolveOwnershipPath(input));
   } catch {
     return resolve(input);
   }
 }
 
+async function ownershipPathVariants(input: string): Promise<string[]> {
+  const variants = new Set([input, await normalizePathForOwnership(input)]);
+  try {
+    variants.add(await ownershipIdentityIo(() => resolveNativeOwnershipPath(input)));
+  } catch {
+    // Missing descendants still match a lexical or established root spelling.
+  }
+  return [...variants];
+}
+
 // Keep lexical variants for missing paths: archive must still recognize a removed
 // worktree below a symlinked worktrees root, whose full realpath no longer exists.
 async function getOwnershipRelativePath(root: string, candidate: string): Promise<string | null> {
-  const roots = [root, await normalizePathForOwnership(root)];
-  const candidates = [candidate, await normalizePathForOwnership(candidate)];
+  const roots = await ownershipPathVariants(root);
+  const candidates = await ownershipPathVariants(candidate);
   for (const rootPath of roots) {
     for (const candidatePath of candidates) {
       const relative = getRelativePathInsideRoot(rootPath, candidatePath);
@@ -1062,7 +1075,7 @@ export async function listPaseoWorktrees({
     envOverlay: READ_ONLY_GIT_ENV,
   });
 
-  const roots = [projectWorktreesRoot, await normalizePathForOwnership(projectWorktreesRoot)];
+  const roots = await ownershipPathVariants(projectWorktreesRoot);
   const worktrees: PaseoWorktreeInfo[] = [];
   // Inspect foreign paths sequentially; a large worktree list must not consume the FS pool.
   for (const entry of parseWorktreeList(stdout)) {