diff --git a/rye/src/bootstrap.rs b/rye/src/bootstrap.rs
index ef58585a34..74a88c6c3d 100644
--- a/rye/src/bootstrap.rs
+++ b/rye/src/bootstrap.rs
@@ -224,6 +224,7 @@ pub fn update_core_shims(shims: &Path, this: &Path) -> Result<(), Error> {
         } else {
             fs::remove_file(shims.join("python")).ok();
             symlink_file(this, shims.join("python")).context("tried to symlink python shim")?;
+            fs::remove_file(shims.join("python3")).ok();
             symlink_file(this, shims.join("python3")).context("tried to symlink python3 shim")?;
         }
     }