diff --git a/crates/gourgeist/src/bare.rs b/crates/gourgeist/src/bare.rs
index 1b686b5ba..f3bcc41a7 100644
--- a/crates/gourgeist/src/bare.rs
+++ b/crates/gourgeist/src/bare.rs
@@ -61,18 +61,39 @@ pub fn create_bare_venv(location: &Utf8Path, interpreter: &Interpreter) -> io::R
     let base_python: Utf8PathBuf = fs_err::canonicalize(interpreter.sys_executable())?
         .try_into()
         .map_err(|err: FromPathBufError| err.into_io_error())?;
-    if location.exists() {
-        if location.join("pyvenv.cfg").is_file() {
-            info!("Removing existing directory");
-            fs::remove_dir_all(location)?;
-        } else {
-            return Err(io::Error::new(
-                io::ErrorKind::AlreadyExists,
-                format!("The directory {location} exists, but it is not virtualenv"),
-            ));
+
+    // Validate the existing location.
+    match location.metadata() {
+        Ok(metadata) => {
+            if metadata.is_file() {
+                return Err(io::Error::new(
+                    io::ErrorKind::AlreadyExists,
+                    format!("File exists at `{location}`"),
+                ));
+            } else if metadata.is_dir() {
+                if location.join("pyvenv.cfg").is_file() {
+                    info!("Removing existing directory");
+                    fs::remove_dir_all(location)?;
+                    fs::create_dir_all(location)?;
+                } else if location
+                    .read_dir()
+                    .is_ok_and(|mut dir| dir.next().is_none())
+                {
+                    info!("Ignoring empty directory");
+                } else {
+                    return Err(io::Error::new(
+                        io::ErrorKind::AlreadyExists,
+                        format!("The directory `{location}` exists, but it's not a virtualenv"),
+                    ));
+                }
+            }
         }
+        Err(err) if err.kind() == io::ErrorKind::NotFound => {
+            fs::create_dir_all(location)?;
+        }
+        Err(err) => return Err(err),
     }
-    fs::create_dir_all(location)?;
+
     // TODO(konstin): I bet on windows we'll have to strip the prefix again
     let location = location.canonicalize_utf8()?;
     let bin_name = if cfg!(unix) {
diff --git a/crates/puffin/tests/venv.rs b/crates/puffin/tests/venv.rs
index 60f382d78..1d38f3440 100644
--- a/crates/puffin/tests/venv.rs
+++ b/crates/puffin/tests/venv.rs
@@ -18,6 +18,7 @@ fn create_venv() -> Result<()> {
     let bin = create_bin_with_executables(&temp_dir, &["3.12"]).expect("Failed to create bin dir");
     let venv = temp_dir.child(".venv");
 
+    // Create a virtual environment at `.venv`.
     let filter_venv = regex::escape(&venv.normalized_display().to_string());
     let filters = &[
         (
@@ -35,6 +36,39 @@ fn create_venv() -> Result<()> {
         .arg(cache_dir.path())
         .arg("--exclude-newer")
         .arg(EXCLUDE_NEWER)
+        .env("PUFFIN_TEST_PYTHON_PATH", bin.clone())
+        .current_dir(&temp_dir), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    Using Python [VERSION] interpreter at [PATH]
+    Creating virtualenv at: /home/ferris/project/.venv
+    "###
+    );
+
+    venv.assert(predicates::path::is_dir());
+
+    // Create a virtual environment at the same location, which should replace it.
+    let filter_venv = regex::escape(&venv.normalized_display().to_string());
+    let filters = &[
+        (
+            r"Using Python 3\.\d+\.\d+ interpreter at .+",
+            "Using Python [VERSION] interpreter at [PATH]",
+        ),
+        (&filter_venv, "/home/ferris/project/.venv"),
+    ];
+    puffin_snapshot!(filters, Command::new(get_bin())
+        .arg("venv")
+        .arg(venv.as_os_str())
+        .arg("--python")
+        .arg("3.12")
+        .arg("--cache-dir")
+        .arg(cache_dir.path())
+        .arg("--exclude-newer")
+        .arg(EXCLUDE_NEWER)
+        .env("PUFFIN_NO_WRAP", "1")
         .env("PUFFIN_TEST_PYTHON_PATH", bin)
         .current_dir(&temp_dir), @r###"
     success: true
@@ -75,6 +109,7 @@ fn create_venv_defaults_to_cwd() -> Result<()> {
         .arg(cache_dir.path())
         .arg("--exclude-newer")
         .arg(EXCLUDE_NEWER)
+        .env("PUFFIN_NO_WRAP", "1")
         .env("PUFFIN_TEST_PYTHON_PATH", bin)
         .current_dir(&temp_dir), @r###"
     success: true
@@ -117,6 +152,7 @@ fn seed() -> Result<()> {
         .arg(cache_dir.path())
         .arg("--exclude-newer")
         .arg(EXCLUDE_NEWER)
+        .env("PUFFIN_NO_WRAP", "1")
         .env("PUFFIN_TEST_PYTHON_PATH", bin)
         .current_dir(&temp_dir), @r###"
     success: true
@@ -154,6 +190,7 @@ fn create_venv_unknown_python_minor() -> Result<()> {
         .arg(cache_dir.path())
         .arg("--exclude-newer")
         .arg(EXCLUDE_NEWER)
+        .env("PUFFIN_NO_WRAP", "1")
         .env("PUFFIN_TEST_PYTHON_PATH", bin)
         .current_dir(&temp_dir);
     if cfg!(windows) {
@@ -208,6 +245,7 @@ fn create_venv_unknown_python_patch() -> Result<()> {
         .arg(cache_dir.path())
         .arg("--exclude-newer")
         .arg(EXCLUDE_NEWER)
+        .env("PUFFIN_NO_WRAP", "1")
         .env("PUFFIN_TEST_PYTHON_PATH", bin)
         .current_dir(&temp_dir), @r###"
     success: false
@@ -248,6 +286,7 @@ fn create_venv_python_patch() -> Result<()> {
         .arg(cache_dir.path())
         .arg("--exclude-newer")
         .arg(EXCLUDE_NEWER)
+        .env("PUFFIN_NO_WRAP", "1")
         .env("PUFFIN_TEST_PYTHON_PATH", bin)
         .current_dir(&temp_dir), @r###"
     success: true
@@ -264,3 +303,143 @@ fn create_venv_python_patch() -> Result<()> {
 
     Ok(())
 }
+
+#[test]
+fn file_exists() -> Result<()> {
+    let temp_dir = assert_fs::TempDir::new()?;
+    let cache_dir = assert_fs::TempDir::new()?;
+    let bin = create_bin_with_executables(&temp_dir, &["3.12"]).expect("Failed to create bin dir");
+    let venv = temp_dir.child(".venv");
+
+    // Create a file at `.venv`. Creating a virtualenv at the same path should fail.
+    venv.touch()?;
+
+    let filter_venv = regex::escape(&venv.normalized_display().to_string());
+    let filters = &[
+        (
+            r"Using Python 3\.\d+\.\d+ interpreter at .+",
+            "Using Python [VERSION] interpreter at [PATH]",
+        ),
+        (&filter_venv, "/home/ferris/project/.venv"),
+    ];
+    puffin_snapshot!(filters, Command::new(get_bin())
+        .arg("venv")
+        .arg(venv.as_os_str())
+        .arg("--python")
+        .arg("3.12")
+        .arg("--cache-dir")
+        .arg(cache_dir.path())
+        .arg("--exclude-newer")
+        .arg(EXCLUDE_NEWER)
+        .env("PUFFIN_NO_WRAP", "1")
+        .env("PUFFIN_TEST_PYTHON_PATH", bin)
+        .current_dir(&temp_dir), @r###"
+    success: false
+    exit_code: 1
+    ----- stdout -----
+
+    ----- stderr -----
+    Using Python [VERSION] interpreter at [PATH]
+    Creating virtualenv at: /home/ferris/project/.venv
+    puffin::venv::creation
+
+      × Failed to create virtualenv
+      ╰─▶ File exists at `/home/ferris/project/.venv`
+    "###
+    );
+
+    Ok(())
+}
+
+#[test]
+fn empty_dir_exists() -> Result<()> {
+    let temp_dir = assert_fs::TempDir::new()?;
+    let cache_dir = assert_fs::TempDir::new()?;
+    let bin = create_bin_with_executables(&temp_dir, &["3.12"]).expect("Failed to create bin dir");
+    let venv = temp_dir.child(".venv");
+
+    // Create an empty directory at `.venv`. Creating a virtualenv at the same path should succeed.
+    venv.create_dir_all()?;
+
+    let filter_venv = regex::escape(&venv.normalized_display().to_string());
+    let filters = &[
+        (
+            r"Using Python 3\.\d+\.\d+ interpreter at .+",
+            "Using Python [VERSION] interpreter at [PATH]",
+        ),
+        (&filter_venv, "/home/ferris/project/.venv"),
+    ];
+    puffin_snapshot!(filters, Command::new(get_bin())
+        .arg("venv")
+        .arg(venv.as_os_str())
+        .arg("--python")
+        .arg("3.12")
+        .arg("--cache-dir")
+        .arg(cache_dir.path())
+        .arg("--exclude-newer")
+        .arg(EXCLUDE_NEWER)
+        .env("PUFFIN_NO_WRAP", "1")
+        .env("PUFFIN_TEST_PYTHON_PATH", bin)
+        .current_dir(&temp_dir), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    Using Python [VERSION] interpreter at [PATH]
+    Creating virtualenv at: /home/ferris/project/.venv
+    "###
+    );
+
+    venv.assert(predicates::path::is_dir());
+
+    Ok(())
+}
+
+#[test]
+fn non_empty_dir_exists() -> Result<()> {
+    let temp_dir = assert_fs::TempDir::new()?;
+    let cache_dir = assert_fs::TempDir::new()?;
+    let bin = create_bin_with_executables(&temp_dir, &["3.12"]).expect("Failed to create bin dir");
+    let venv = temp_dir.child(".venv");
+
+    // Create a non-empty directory at `.venv`. Creating a virtualenv at the same path should fail.
+    venv.create_dir_all()?;
+    venv.child("file").touch()?;
+
+    let filter_venv = regex::escape(&venv.normalized_display().to_string());
+    let filters = &[
+        (
+            r"Using Python 3\.\d+\.\d+ interpreter at .+",
+            "Using Python [VERSION] interpreter at [PATH]",
+        ),
+        (&filter_venv, "/home/ferris/project/.venv"),
+    ];
+    puffin_snapshot!(filters, Command::new(get_bin())
+        .arg("venv")
+        .arg(venv.as_os_str())
+        .arg("--python")
+        .arg("3.12")
+        .arg("--cache-dir")
+        .arg(cache_dir.path())
+        .arg("--exclude-newer")
+        .arg(EXCLUDE_NEWER)
+        .env("PUFFIN_NO_WRAP", "1")
+        .env("PUFFIN_TEST_PYTHON_PATH", bin)
+        .current_dir(&temp_dir), @r###"
+    success: false
+    exit_code: 1
+    ----- stdout -----
+
+    ----- stderr -----
+    Using Python [VERSION] interpreter at [PATH]
+    Creating virtualenv at: /home/ferris/project/.venv
+    puffin::venv::creation
+
+      × Failed to create virtualenv
+      ╰─▶ The directory `/home/ferris/project/.venv` exists, but it's not a virtualenv
+    "###
+    );
+
+    Ok(())
+}