diff --git a/README.md b/README.md
index aff64c8..81f218b 100644
--- a/README.md
+++ b/README.md
@@ -62,6 +62,19 @@ Entering worktree: feature/payments
 (wt) $          # Your changes are here
 ```
 
+Re-running `wt new <name>` for an existing worktree drops you back into it —
+no error, no stash:
+
+```bash
+$ wt new feature/auth
+Worktree 'feature/auth' already exists at /…/.worktrees/feature--auth, entering it.
+(wt) $
+```
+
+If a directory exists under `.worktrees/` but is not registered with git
+(e.g. after a partial `wt rm`), `wt new` exits with an actionable error and
+leaves the directory untouched.
+
 ### Switch workspaces
 
 ```bash
diff --git a/commands/do.md b/commands/do.md
index c957ba1..859708f 100644
--- a/commands/do.md
+++ b/commands/do.md
@@ -46,7 +46,9 @@ curl -s -H "Shortcut-Token: $SHORTCUT_API_TOKEN" \
 wt new <branch-name> --print-path
 ```
 
-This prints the worktree path. Capture it.
+This prints the worktree path. Capture it. Re-running this command for an
+already-created worktree is safe — it prints the existing path and exits 0
+without spawning a shell or creating a stash.
 
 ### 4. Set working context
 
diff --git a/src/main.rs b/src/main.rs
index af8289b..c62142c 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -172,6 +172,22 @@ fn cmd_new(config: &RepoConfig, name: Option<String>, base: &str, print_path: bo
         }
     };
 
+    let manager = WorktreeManager::new(config.root.clone())?;
+
+    if let Some(info) = manager.get_worktree_info(&name)? {
+        eprintln!(
+            "Worktree '{}' already exists at {}, entering it.",
+            name,
+            info.path.display()
+        );
+        if print_path {
+            println!("{}", info.path.display());
+        } else {
+            spawn_wt_shell(&info.path, &info.task_id, &info.branch)?;
+        }
+        return Ok(());
+    }
+
     // If creating worktree for currently checked out branch, migrate the work
     let migrating = name == current_branch && current_branch != root_branch;
     let had_changes = if migrating {
@@ -180,7 +196,6 @@ fn cmd_new(config: &RepoConfig, name: Option<String>, base: &str, print_path: bo
         false
     };
 
-    let manager = WorktreeManager::new(config.root.clone())?;
     ensure_worktrees_in_gitignore(&config.root, &config.worktree_dir)?;
     std::fs::create_dir_all(&config.worktree_dir)?;
     let path = manager.create_worktree(&name, base, &config.worktree_dir, |remotes| {
diff --git a/src/worktree_manager.rs b/src/worktree_manager.rs
index 17c8f51..a5deda1 100644
--- a/src/worktree_manager.rs
+++ b/src/worktree_manager.rs
@@ -169,7 +169,22 @@ impl WorktreeManager {
         let worktree_path = worktree_dir.join(&safe_name);
 
         if worktree_path.exists() {
-            anyhow::bail!("Worktree path already exists: {:?}", worktree_path);
+            let registered = self
+                .list_worktrees()?
+                .into_iter()
+                .any(|w| w.path == worktree_path);
+            if registered {
+                anyhow::bail!(
+                    "Worktree '{}' is already registered at {:?}",
+                    task_id,
+                    worktree_path
+                );
+            }
+            anyhow::bail!(
+                "Path {:?} exists but is not a registered worktree.\n\
+                 Remove the directory before retrying.",
+                worktree_path
+            );
         }
 
         let mut upstream_branch: Option<String> = None;
@@ -601,6 +616,10 @@ mod tests {
             |_| unreachable!(),
         );
         assert!(result.is_err());
+        assert!(result
+            .unwrap_err()
+            .to_string()
+            .contains("already registered"));
     }
 
     #[test]
diff --git a/tests/new_resume_test.rs b/tests/new_resume_test.rs
new file mode 100644
index 0000000..ba46b18
--- /dev/null
+++ b/tests/new_resume_test.rs
@@ -0,0 +1,139 @@
+use std::process::Command;
+use tempfile::TempDir;
+use wt::worktree_manager::WorktreeManager;
+
+fn setup_git_repo() -> TempDir {
+    let temp_dir = TempDir::new().unwrap();
+    let repo_path = temp_dir.path();
+
+    Command::new("git")
+        .args(["init", "-b", "main"])
+        .current_dir(repo_path)
+        .output()
+        .unwrap();
+
+    Command::new("git")
+        .args(["config", "user.email", "test@example.com"])
+        .current_dir(repo_path)
+        .output()
+        .unwrap();
+
+    Command::new("git")
+        .args(["config", "user.name", "Test User"])
+        .current_dir(repo_path)
+        .output()
+        .unwrap();
+
+    std::fs::write(repo_path.join("README.md"), "# Test Repo\n").unwrap();
+
+    Command::new("git")
+        .args(["add", "."])
+        .current_dir(repo_path)
+        .output()
+        .unwrap();
+
+    Command::new("git")
+        .args(["commit", "-m", "Initial commit"])
+        .current_dir(repo_path)
+        .output()
+        .unwrap();
+
+    temp_dir
+}
+
+#[test]
+fn test_create_worktree_fresh_succeeds() {
+    let repo = setup_git_repo();
+    let worktree_dir = TempDir::new().unwrap();
+
+    let manager = WorktreeManager::new(repo.path().to_path_buf()).unwrap();
+    let result = manager.create_worktree(
+        "fresh-feature",
+        "main",
+        worktree_dir.path(),
+        |_| unreachable!(),
+    );
+
+    assert!(result.is_ok(), "fresh create should succeed: {:?}", result);
+    let path = result.unwrap();
+    assert!(path.exists());
+    assert!(manager.worktree_exists("fresh-feature"));
+}
+
+#[test]
+fn test_create_worktree_already_registered_errors_at_manager_layer() {
+    let repo = setup_git_repo();
+    let worktree_dir = TempDir::new().unwrap();
+
+    let manager = WorktreeManager::new(repo.path().to_path_buf()).unwrap();
+    manager
+        .create_worktree(
+            "dup-feature",
+            "main",
+            worktree_dir.path(),
+            |_| unreachable!(),
+        )
+        .unwrap();
+
+    let result = manager.create_worktree(
+        "dup-feature",
+        "main",
+        worktree_dir.path(),
+        |_| unreachable!(),
+    );
+
+    assert!(result.is_err());
+    let msg = result.unwrap_err().to_string();
+    assert!(
+        msg.contains("already registered"),
+        "expected 'already registered' in error: {msg}"
+    );
+}
+
+#[test]
+fn test_create_worktree_orphan_directory_errors() {
+    let repo = setup_git_repo();
+    let worktree_dir = TempDir::new().unwrap();
+
+    let manager = WorktreeManager::new(repo.path().to_path_buf()).unwrap();
+    let path = manager
+        .create_worktree(
+            "orphan-feature",
+            "main",
+            worktree_dir.path(),
+            |_| unreachable!(),
+        )
+        .unwrap();
+
+    // Deregister from git but leave the directory on disk
+    Command::new("git")
+        .args(["worktree", "remove", "--force", path.to_str().unwrap()])
+        .current_dir(repo.path())
+        .output()
+        .unwrap();
+
+    // Write a marker file to prove the directory is not cleaned up on error
+    let marker = path.join("user_work.txt");
+    std::fs::create_dir_all(&path).unwrap();
+    std::fs::write(&marker, "precious work").unwrap();
+
+    let result = manager.create_worktree(
+        "orphan-feature",
+        "main",
+        worktree_dir.path(),
+        |_| unreachable!(),
+    );
+
+    assert!(result.is_err());
+    let msg = result.unwrap_err().to_string();
+    assert!(
+        msg.contains("not a registered worktree"),
+        "expected actionable error, got: {msg}"
+    );
+    assert!(
+        msg.contains("Remove the directory"),
+        "expected removal hint in error: {msg}"
+    );
+    // Directory must not be deleted
+    assert!(marker.exists(), "orphan directory must not be auto-cleaned");
+}