diff --git a/cli/tools/upgrade.rs b/cli/tools/upgrade.rs
index 933dad095a..0748b4e8b8 100644
--- a/cli/tools/upgrade.rs
+++ b/cli/tools/upgrade.rs
@@ -265,13 +265,15 @@ pub async fn upgrade(
 ) -> Result<(), AnyError> {
   let ps = ProcState::build(flags).await?;
   let current_exe_path = std::env::current_exe()?;
-  let metadata = fs::metadata(&current_exe_path)?;
+  let output_exe_path =
+    upgrade_flags.output.as_ref().unwrap_or(&current_exe_path);
+  let metadata = fs::metadata(output_exe_path)?;
   let permissions = metadata.permissions();
 
   if permissions.readonly() {
     bail!(
       "You do not have write permission to {}",
-      current_exe_path.display()
+      output_exe_path.display()
     );
   }
   #[cfg(unix)]
@@ -282,7 +284,7 @@ pub async fn upgrade(
       "You don't have write permission to {} because it's owned by root.\n",
       "Consider updating deno through your package manager if its installed from it.\n",
       "Otherwise run `deno upgrade` as root.",
-    ), current_exe_path.display());
+    ), output_exe_path.display());
   }
 
   let client = &ps.http_client;