diff --git a/cli/js/tests/remove_test.ts b/cli/js/tests/remove_test.ts
index 4c0bb6768e..8de577838c 100644
--- a/cli/js/tests/remove_test.ts
+++ b/cli/js/tests/remove_test.ts
@@ -479,3 +479,48 @@ unitTest({ perms: { write: false } }, async function removeAllPerm(): Promise<
   assert(err instanceof Deno.errors.PermissionDenied);
   assertEquals(err.name, "PermissionDenied");
 });
+
+if (Deno.build.os === "windows") {
+  unitTest(
+    { perms: { run: true, write: true, read: true } },
+    async function removeFileSymlink(): Promise<void> {
+      const symlink = Deno.run({
+        cmd: ["cmd", "/c", "mklink", "file_link", "bar"],
+        stdout: "null",
+      });
+
+      assert(await symlink.status());
+      symlink.close();
+      await Deno.remove("file_link");
+      let err;
+      try {
+        await Deno.lstat("file_link");
+      } catch (e) {
+        err = e;
+      }
+      assert(err instanceof Deno.errors.NotFound);
+    }
+  );
+
+  unitTest(
+    { perms: { run: true, write: true, read: true } },
+    async function removeDirSymlink(): Promise<void> {
+      const symlink = Deno.run({
+        cmd: ["cmd", "/c", "mklink", "/d", "dir_link", "bar"],
+        stdout: "null",
+      });
+
+      assert(await symlink.status());
+      symlink.close();
+
+      await Deno.remove("dir_link");
+      let err;
+      try {
+        await Deno.lstat("dir_link");
+      } catch (e) {
+        err = e;
+      }
+      assert(err instanceof Deno.errors.NotFound);
+    }
+  );
+}
diff --git a/cli/ops/fs.rs b/cli/ops/fs.rs
index 116366c8dc..068dbaf7ec 100644
--- a/cli/ops/fs.rs
+++ b/cli/ops/fs.rs
@@ -394,13 +394,29 @@ fn op_remove(
 
   let is_sync = args.promise_id.is_none();
   blocking_json(is_sync, move || {
+    #[cfg(not(unix))]
+    use std::os::windows::prelude::MetadataExt;
+
     let metadata = std::fs::symlink_metadata(&path)?;
+
     debug!("op_remove {} {}", path.display(), recursive);
     let file_type = metadata.file_type();
-    if file_type.is_file() || file_type.is_symlink() {
+    if file_type.is_file() {
       std::fs::remove_file(&path)?;
     } else if recursive {
       std::fs::remove_dir_all(&path)?;
+    } else if file_type.is_symlink() {
+      #[cfg(unix)]
+      std::fs::remove_file(&path)?;
+      #[cfg(not(unix))]
+      {
+        use winapi::um::winnt::FILE_ATTRIBUTE_DIRECTORY;
+        if metadata.file_attributes() & FILE_ATTRIBUTE_DIRECTORY != 0 {
+          std::fs::remove_dir(&path)?;
+        } else {
+          std::fs::remove_file(&path)?;
+        }
+      }
     } else {
       std::fs::remove_dir(&path)?;
     }