From 385673f420697274d788c614a00fba4cd3f47f21 Mon Sep 17 00:00:00 2001
From: Chris Wanstrath <chris@ozmm.org>
Date: Mon, 9 Mar 2026 12:04:04 -0700
Subject: [PATCH] Refactor symlink removal into unlinkSessionSymlink helper

---
 src/commands/cleanup.ts |  5 ++---
 src/commands/helpers.ts | 30 +++++++++++++++++++++++-------
 src/commands/new.ts     | 13 +++++++------
 3 files changed, 32 insertions(+), 16 deletions(-)

diff --git a/src/commands/cleanup.ts b/src/commands/cleanup.ts
index 599b05b..51fd1dc 100644
--- a/src/commands/cleanup.ts
+++ b/src/commands/cleanup.ts
@@ -1,8 +1,7 @@
-import { join } from "path"
 import { existsSync } from "fs"
-import { unlink } from "fs/promises"
 import * as git from "../git.ts"
 import * as state from "../state.ts"
+import { unlinkSessionSymlink } from "./helpers.ts"
 
 export async function action() {
   const root = await git.repoRoot()
@@ -23,7 +22,7 @@ export async function action() {
 
   for (const s of stale) {
     await state.removeSession(root, s.branch)
-    await unlink(join(root, '.sandlot', s.branch)).catch(() => {})
+    await unlinkSessionSymlink(root, s.branch)
     console.log(`✔ Removed stale session: ${s.branch}`)
   }
 }
diff --git a/src/commands/helpers.ts b/src/commands/helpers.ts
index 6270ea8..fbb45fa 100644
--- a/src/commands/helpers.ts
+++ b/src/commands/helpers.ts
@@ -1,6 +1,6 @@
-import { basename, join } from "path"
+import { basename, dirname, join } from "path"
 import { homedir } from "os"
-import { mkdir, symlink, unlink } from "fs/promises"
+import { mkdir, readdir, rmdir, symlink, unlink } from "fs/promises"
 import { $ } from "bun"
 import * as git from "../git.ts"
 import * as vm from "../vm.ts"
@@ -9,6 +9,22 @@ import { spinner } from "../spinner.ts"
 import { die } from "../fmt.ts"
 import type { Session } from "../state.ts"
 
+/** Remove a .sandlot/<branch> symlink and prune empty parent dirs up to .sandlot/. */
+export async function unlinkSessionSymlink(root: string, branch: string): Promise<void> {
+  const sandlotDir = join(root, '.sandlot')
+  const symlinkPath = join(sandlotDir, branch)
+  await unlink(symlinkPath).catch(() => {})
+
+  // Walk up from the symlink's parent, removing empty dirs, stopping at .sandlot/ itself
+  let dir = dirname(symlinkPath)
+  while (dir !== sandlotDir) {
+    const entries = await readdir(dir).catch(() => null)
+    if (!entries || entries.length > 0) break
+    await rmdir(dir).catch(() => {})
+    dir = dirname(dir)
+  }
+}
+
 /** Look up a session by branch, dying if it doesn't exist. */
 export async function requireSession(branch: string): Promise<{ root: string; session: Session }> {
   const root = await git.repoRoot()
@@ -35,12 +51,13 @@ export async function ensureSession(branch: string): Promise<{ root: string; ses
   const worktreeAbs = join(homedir(), '.sandlot', basename(root), branch)
   try {
     await git.createWorktree(branch, worktreeAbs, root)
-    await mkdir(join(root, '.sandlot'), { recursive: true })
-    await symlink(worktreeAbs, join(root, '.sandlot', branch))
+    const symlinkPath = join(root, '.sandlot', branch)
+    await mkdir(dirname(symlinkPath), { recursive: true })
+    await symlink(worktreeAbs, symlinkPath)
   } catch (err) {
     // Clean up on failure — but do NOT delete the branch (it already existed)
     await git.removeWorktree(worktreeAbs, root).catch(() => {})
-    await unlink(join(root, '.sandlot', branch)).catch(() => {})
+    await unlinkSessionSymlink(root, branch)
     die(`Failed to recreate session: ${(err as Error).message ?? err}`)
   }
 
@@ -60,8 +77,7 @@ export async function teardownSession(root: string, branch: string, worktree: st
   await git.removeWorktree(worktree, root)
     .catch((e) => console.warn(`⚠ Failed to remove worktree: ${e.message}`))
 
-  await unlink(join(root, '.sandlot', branch))
-    .catch(() => {}) // symlink may not exist
+  await unlinkSessionSymlink(root, branch)
 
   await state.removeSession(root, branch)
 }
diff --git a/src/commands/new.ts b/src/commands/new.ts
index 5b76f8f..2d85e7e 100644
--- a/src/commands/new.ts
+++ b/src/commands/new.ts
@@ -1,6 +1,6 @@
-import { basename, join } from "path"
+import { basename, dirname, join } from "path"
 import { homedir } from "os"
-import { mkdir, symlink, unlink } from "fs/promises"
+import { mkdir, symlink } from "fs/promises"
 import * as git from "../git.ts"
 import * as vm from "../vm.ts"
 import * as state from "../state.ts"
@@ -8,7 +8,7 @@ import { spinner } from "../spinner.ts"
 import { die } from "../fmt.ts"
 import { requireApiKey } from "../env.ts"
 import { renderMarkdown } from "../markdown.ts"
-import { saveChanges } from "./helpers.ts"
+import { saveChanges, unlinkSessionSymlink } from "./helpers.ts"
 
 const ADJECTIVES = [
   "calm", "bold", "warm", "cool", "keen", "soft", "fast", "wild", "fair", "rare",
@@ -99,8 +99,9 @@ export async function action(
   const spin = spinner("Creating worktree", branch)
   try {
     await git.createWorktree(branch, worktreeAbs, root)
-    await mkdir(join(root, '.sandlot'), { recursive: true })
-    await symlink(worktreeAbs, join(root, '.sandlot', branch))
+    const symlinkPath = join(root, '.sandlot', branch)
+    await mkdir(dirname(symlinkPath), { recursive: true })
+    await symlink(worktreeAbs, symlinkPath)
 
     spin.text = "Starting container"
     await vm.ensure((msg) => { spin.text = msg })
@@ -109,7 +110,7 @@ export async function action(
     spin.fail(String((err as Error).message ?? err))
     await git.removeWorktree(worktreeAbs, root).catch(() => {})
     await git.deleteLocalBranch(branch, root).catch(() => {})
-    await unlink(join(root, '.sandlot', branch)).catch(() => {})
+    await unlinkSessionSymlink(root, branch)
     process.exit(1)
   }