diff --git a/crates/uv-install-wheel/src/wheel.rs b/crates/uv-install-wheel/src/wheel.rs
index 8d518b9e0..559237e16 100644
--- a/crates/uv-install-wheel/src/wheel.rs
+++ b/crates/uv-install-wheel/src/wheel.rs
@@ -143,7 +143,7 @@ fn format_shebang(executable: impl AsRef<Path>, os_name: &str, relocatable: bool
         // (note: the Windows trampoline binaries natively support relative paths to executable)
         if shebang_length > 127 || executable.contains(' ') || relocatable {
             let prefix = if relocatable {
-                r#""$(CDPATH= cd -- "$(dirname -- "$0")" && echo "$PWD")"/"#
+                r#""$(dirname -- "$(realpath -- "$0")")"/"#
             } else {
                 ""
             };
@@ -1019,7 +1019,7 @@ mod test {
         let os_name = "posix";
         assert_eq!(
             format_shebang(executable, os_name, true),
-            "#!/bin/sh\n'''exec' \"$(CDPATH= cd -- \"$(dirname -- \"$0\")\" && echo \"$PWD\")\"/'python3' \"$0\" \"$@\"\n' '''"
+            "#!/bin/sh\n'''exec' \"$(dirname -- \"$(realpath -- \"$0\")\")\"/'python3' \"$0\" \"$@\"\n' '''"
         );
 
         // Except on Windows...
diff --git a/crates/uv-virtualenv/src/virtualenv.rs b/crates/uv-virtualenv/src/virtualenv.rs
index d46839707..70f0ca22e 100644
--- a/crates/uv-virtualenv/src/virtualenv.rs
+++ b/crates/uv-virtualenv/src/virtualenv.rs
@@ -298,9 +298,7 @@ pub(crate) fn create(
 
         let virtual_env_dir = match (relocatable, name.to_owned()) {
             (true, "activate") => {
-                // Extremely verbose, but should cover all major POSIX shells,
-                // as well as platforms where `readlink` does not implement `-f`.
-                r#"'"$(dirname -- "$(CDPATH= cd -- "$(dirname -- "$SCRIPT_PATH")" > /dev/null && echo "$PWD")")"'"#
+                r#"'"$(dirname -- "$(dirname -- "$(realpath -- "$SCRIPT_PATH")")")"'"#
             }
             (true, "activate.bat") => r"%~dp0..",
             (true, "activate.fish") => {
diff --git a/crates/uv/tests/pip_install.rs b/crates/uv/tests/pip_install.rs
index be6ee3a49..610a3c3e0 100644
--- a/crates/uv/tests/pip_install.rs
+++ b/crates/uv/tests/pip_install.rs
@@ -6810,6 +6810,18 @@ fn install_relocatable() -> Result<()> {
         .success()
         .stdout(predicate::str::contains("Hello world!"));
 
+    // Relocatable entrypoint should still be usable even if symlinked.
+    // Only testable on POSIX since symlinks require elevated privilege on Windows
+    #[cfg(unix)]
+    {
+        let script_symlink_path = context.temp_dir.join("black");
+        std::os::unix::fs::symlink(script_path, script_symlink_path.clone())?;
+        Command::new(script_symlink_path.as_os_str())
+            .assert()
+            .success()
+            .stdout(predicate::str::contains("Hello world!"));
+    }
+
     Ok(())
 }
 
diff --git a/crates/uv/tests/venv.rs b/crates/uv/tests/venv.rs
index 53afcee72..b7dd0d6cf 100644
--- a/crates/uv/tests/venv.rs
+++ b/crates/uv/tests/venv.rs
@@ -957,7 +957,9 @@ fn verify_pyvenv_cfg_relocatable() {
 
     let activate_sh = scripts.child("activate");
     activate_sh.assert(predicates::path::is_file());
-    activate_sh.assert(predicates::str::contains(r#"VIRTUAL_ENV=''"$(dirname -- "$(CDPATH= cd -- "$(dirname -- "$SCRIPT_PATH")" > /dev/null && echo "$PWD")")"''"#));
+    activate_sh.assert(predicates::str::contains(
+        r#"VIRTUAL_ENV=''"$(dirname -- "$(dirname -- "$(realpath -- "$SCRIPT_PATH")")")"''"#,
+    ));
 
     let activate_bat = scripts.child("activate.bat");
     activate_bat.assert(predicates::path::is_file());