diff --git a/vscode/src/test/suite/ruby/rubyInstaller.test.ts b/vscode/src/test/suite/ruby/rubyInstaller.test.ts
index 6775316975..8dc5e14b80 100644
--- a/vscode/src/test/suite/ruby/rubyInstaller.test.ts
+++ b/vscode/src/test/suite/ruby/rubyInstaller.test.ts
@@ -3,12 +3,13 @@ import assert from "assert";
 import path from "path";
 import os from "os";
 
+import sinon from "sinon";
 import { before, after } from "mocha";
 import * as vscode from "vscode";
 
 import { RubyInstaller } from "../../../ruby/rubyInstaller";
 import { WorkspaceChannel } from "../../../workspaceChannel";
-import { LOG_CHANNEL } from "../../../common";
+import { asyncExec, LOG_CHANNEL } from "../../../common";
 import { RUBY_VERSION } from "../../rubyVersion";
 
 suite("RubyInstaller", () => {
@@ -100,4 +101,39 @@ suite("RubyInstaller", () => {
       force: true,
     });
   });
+
+  test("Finds Ruby using Powershell", async () => {
+    const [major, minor, _patch] = RUBY_VERSION.split(".").map(Number);
+    fs.symlinkSync(
+      path.join(
+        "C:",
+        "hostedtoolcache",
+        "windows",
+        "Ruby",
+        RUBY_VERSION,
+        "x64",
+      ),
+      path.join("C:", `Ruby${major}${minor}-${os.arch()}`),
+    );
+
+    fs.writeFileSync(path.join(workspacePath, ".ruby-version"), RUBY_VERSION);
+
+    const windows = new RubyInstaller(workspaceFolder, outputChannel);
+
+    const { stdout } = await asyncExec("where powershell");
+    const stub = sinon.stub(vscode.env, "shell").returns(stdout.trim());
+
+    const { env, version, yjit } = await windows.activate();
+    stub.restore();
+
+    assert.match(env.GEM_PATH!, /ruby\/3\.3\.0/);
+    assert.match(env.GEM_PATH!, /lib\/ruby\/gems\/3\.3\.0/);
+    assert.strictEqual(version, RUBY_VERSION);
+    assert.notStrictEqual(yjit, undefined);
+
+    fs.rmSync(path.join("C:", `Ruby${major}${minor}-${os.arch()}`), {
+      recursive: true,
+      force: true,
+    });
+  });
 });