diff --git a/cli/tools/standalone.rs b/cli/tools/standalone.rs
index 8cc574e505..884d2a31da 100644
--- a/cli/tools/standalone.rs
+++ b/cli/tools/standalone.rs
@@ -48,7 +48,11 @@ pub async fn get_base_binary(
   }
 
   let archive_data = tokio::fs::read(binary_path).await?;
-  let base_binary_path = crate::tools::upgrade::unpack(archive_data, exe_name)?;
+  let base_binary_path = crate::tools::upgrade::unpack(
+    archive_data,
+    exe_name,
+    target.contains("windows"),
+  )?;
   let base_binary = tokio::fs::read(base_binary_path).await?;
   Ok(base_binary)
 }
diff --git a/cli/tools/upgrade.rs b/cli/tools/upgrade.rs
index e00127fa47..e98ecf5ff1 100644
--- a/cli/tools/upgrade.rs
+++ b/cli/tools/upgrade.rs
@@ -109,7 +109,7 @@ pub async fn upgrade_command(
   println!("Deno is upgrading to version {}", &install_version);
 
   let old_exe_path = std::env::current_exe()?;
-  let new_exe_path = unpack(archive_data, "deno")?;
+  let new_exe_path = unpack(archive_data, "deno", cfg!(windows))?;
   let permissions = fs::metadata(&old_exe_path)?.permissions();
   fs::set_permissions(&new_exe_path, permissions)?;
   check_exe(&new_exe_path)?;
@@ -177,12 +177,13 @@ async fn download_package(
 pub fn unpack(
   archive_data: Vec<u8>,
   exe_name: &str,
+  is_windows: bool,
 ) -> Result<PathBuf, std::io::Error> {
   // We use into_path so that the tempdir is not automatically deleted. This is
   // useful for debugging upgrade, but also so this function can return a path
   // to the newly uncompressed file without fear of the tempdir being deleted.
   let temp_dir = TempDir::new()?.into_path();
-  let exe_ext = if cfg!(windows) { "exe" } else { "" };
+  let exe_ext = if is_windows { "exe" } else { "" };
   let archive_path = temp_dir.join(exe_name).with_extension(".zip");
   let exe_path = temp_dir.join(exe_name).with_extension(exe_ext);
   assert!(!exe_path.exists());