diff --git a/cli/tools/upgrade.rs b/cli/tools/upgrade.rs
index 78ac599815..f37ee8455d 100644
--- a/cli/tools/upgrade.rs
+++ b/cli/tools/upgrade.rs
@@ -270,25 +270,31 @@ pub async fn upgrade(
   let factory = CliFactory::from_flags(flags).await?;
   let client = factory.http_client();
   let current_exe_path = std::env::current_exe()?;
-  let metadata = fs::metadata(&current_exe_path)?;
-  let permissions = metadata.permissions();
+  let output_exe_path =
+    upgrade_flags.output.as_ref().unwrap_or(&current_exe_path);
 
-  if permissions.readonly() {
-    bail!(
-      "You do not have write permission to {}",
-      current_exe_path.display()
-    );
-  }
-  #[cfg(unix)]
-  if std::os::unix::fs::MetadataExt::uid(&metadata) == 0
-    && !nix::unistd::Uid::effective().is_root()
-  {
-    bail!(concat!(
-      "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());
-  }
+  let permissions = if let Ok(metadata) = fs::metadata(output_exe_path) {
+    let permissions = metadata.permissions();
+    if permissions.readonly() {
+      bail!(
+        "You do not have write permission to {}",
+        output_exe_path.display()
+      );
+    }
+    #[cfg(unix)]
+    if std::os::unix::fs::MetadataExt::uid(&metadata) == 0
+      && !nix::unistd::Uid::effective().is_root()
+    {
+      bail!(concat!(
+        "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.",
+      ), output_exe_path.display());
+    }
+    permissions
+  } else {
+    fs::metadata(&current_exe_path)?.permissions()
+  };
 
   let install_version = match upgrade_flags.version {
     Some(passed_version) => {