diff --git a/test/unit/node/proxy.test.ts b/test/unit/node/proxy.test.ts
index febc8a6db..b40819cc1 100644
--- a/test/unit/node/proxy.test.ts
+++ b/test/unit/node/proxy.test.ts
@@ -1,5 +1,9 @@
 import bodyParser from "body-parser"
 import * as express from "express"
+import * as nodeFetch from "node-fetch"
+import * as http from "http"
+import { HttpCode } from "../../../src/common/http"
+import { proxy } from "../../../src/node/proxy"
 import * as httpserver from "../../utils/httpserver"
 import * as integration from "../../utils/integration"
 
@@ -102,4 +106,107 @@ describe("proxy", () => {
     expect(resp.status).toBe(200)
     expect(await resp.json()).toBe("coder is the best")
   })
+
+  it("should handle bad requests", async () => {
+    e.use(bodyParser.json({ strict: false }))
+    e.post("/wsup", (req, res) => {
+      res.json(req.body)
+    })
+    codeServer = await integration.setup(["--auth=none"], "")
+    const resp = await codeServer.fetch(proxyPath, {
+      method: "post",
+      body: "coder is the best",
+      headers: {
+        "Content-Type": "application/json",
+      },
+    })
+    expect(resp.status).toBe(400)
+    expect(resp.statusText).toMatch("Bad Request")
+  })
+
+  it("should handle invalid routes", async () => {
+    e.post("/wsup", (req, res) => {
+      res.json(req.body)
+    })
+    codeServer = await integration.setup(["--auth=none"], "")
+    const resp = await codeServer.fetch(`${proxyPath}/hello`)
+    expect(resp.status).toBe(404)
+    expect(resp.statusText).toMatch("Not Found")
+  })
+
+  it("should handle errors", async () => {
+    e.use(bodyParser.json({ strict: false }))
+    e.post("/wsup", (req, res) => {
+      throw new Error("BROKEN")
+    })
+    codeServer = await integration.setup(["--auth=none"], "")
+    const resp = await codeServer.fetch(proxyPath, {
+      method: "post",
+      body: JSON.stringify("coder is the best"),
+      headers: {
+        "Content-Type": "application/json",
+      },
+    })
+    expect(resp.status).toBe(500)
+    expect(resp.statusText).toMatch("Internal Server Error")
+  })
+})
+
+// NOTE@jsjoeio
+// Both this test suite and the one above it are very similar
+// The main difference is this one uses http and node-fetch
+// and specifically tests the proxy in isolation vs. using
+// the httpserver abstraction we've built.
+//
+// Leaving this as a separate test suite for now because
+// we may consider refactoring the httpserver abstraction
+// in the future.
+//
+// If you're writing a test specifically for code in
+// src/node/proxy.ts, you should probably add it to
+// this test suite.
+describe("proxy (standalone)", () => {
+  const PORT = 9003
+  const PROXY_PORT = 8003
+  const URL = `http://localhost:${PORT}`
+  const PROXY_URL = `http://localhost:${PROXY_PORT}`
+  let testServer: http.Server
+  let proxyTarget: http.Server
+
+  beforeEach(async () => {
+    // Define server and a proxy server
+    testServer = http.createServer((req, res) => {
+      proxy.web(req, res, {
+        target: PROXY_URL,
+      })
+    })
+
+    proxyTarget = http.createServer((req, res) => {
+      res.writeHead(200, { "Content-Type": "text/plain" })
+      res.end()
+    })
+
+    // Start both servers
+    await proxyTarget.listen(PROXY_PORT)
+    await testServer.listen(PORT)
+  })
+
+  afterEach(async () => {
+    await testServer.close()
+    await proxyTarget.close()
+  })
+
+  it("should return a 500 when proxy target errors ", async () => {
+    // Close the proxy target so that proxy errors
+    await proxyTarget.close()
+    const errorResp = await nodeFetch.default(`${URL}/error`)
+    expect(errorResp.status).toBe(HttpCode.ServerError)
+    expect(errorResp.statusText).toBe("Internal Server Error")
+  })
+
+  it("should proxy correctly", async () => {
+    const resp = await nodeFetch.default(`${URL}/route`)
+    expect(resp.status).toBe(200)
+    expect(resp.statusText).toBe("OK")
+  })
 })