diff --git a/test/e2e/baseFixture.ts b/test/e2e/baseFixture.ts
index 3778593d6..1efad7f7a 100644
--- a/test/e2e/baseFixture.ts
+++ b/test/e2e/baseFixture.ts
@@ -70,8 +70,8 @@ export const test = base.extend<TestFixtures>({
     // made too). In these cases just accept.
     page.on("dialog", (d) => d.accept())
 
-    const codeServerPage = new CodeServerPage(codeServer, page)
-    await codeServerPage.setup(authenticated)
+    const codeServerPage = new CodeServerPage(codeServer, page, authenticated)
+    await codeServerPage.navigate()
     await use(codeServerPage)
   },
 })
diff --git a/test/e2e/codeServer.test.ts b/test/e2e/codeServer.test.ts
index 5d09f3331..30e8cc6c5 100644
--- a/test/e2e/codeServer.test.ts
+++ b/test/e2e/codeServer.test.ts
@@ -1,8 +1,45 @@
+import * as cp from "child_process"
 import { promises as fs } from "fs"
+import * as os from "os"
 import * as path from "path"
+import * as util from "util"
 import { describe, test, expect } from "./baseFixture"
+import { CodeServer } from "./models/CodeServer"
+
+describe("code-server", true, [], {}, () => {
+  // TODO@asher: Generalize this?  Could be nice if we were to ever need
+  // multiple migration tests in other suites.
+  const instances = new Map<string, CodeServer>()
+  test.afterAll(async () => {
+    const procs = Array.from(instances.values())
+    instances.clear()
+    await Promise.all(procs.map((cs) => cs.close()))
+  })
+
+  /**
+   * Spawn a specific version of code-server using the install script.
+   */
+  const spawn = async (version: string, dir?: string): Promise<CodeServer> => {
+    let instance = instances.get(version)
+    if (!instance) {
+      await util.promisify(cp.exec)(`./install.sh --method standalone --version ${version}`, {
+        cwd: path.join(__dirname, "../.."),
+      })
+
+      instance = new CodeServer(
+        "code-server@" + version,
+        ["--auth=none"],
+        { VSCODE_DEV: "" },
+        dir,
+        `${os.homedir()}/.local/lib/code-server-${version}`,
+      )
+
+      instances.set(version, instance)
+    }
+
+    return instance
+  }
 
-describe("CodeServer", true, [], {}, () => {
   test("should navigate to home page", async ({ codeServerPage }) => {
     // We navigate codeServer before each test
     // and we start the test with a storage state
@@ -34,24 +71,50 @@ describe("CodeServer", true, [], {}, () => {
     await codeServerPage.openFile(file)
   })
 
-  test("should not share state with other paths", async ({ codeServerPage }) => {
+  test("should migrate state to avoid collisions", async ({ codeServerPage }) => {
+    // This can take a very long time in development because of how long pages
+    // take to load and we are doing a lot of that here.
+    test.slow()
+
     const dir = await codeServerPage.workspaceDir
-    const file = path.join(dir, "foo")
-    await fs.writeFile(file, "bar")
+    const files = [path.join(dir, "foo"), path.join(dir, "bar")]
+    await Promise.all(
+      files.map((file) => {
+        return fs.writeFile(file, path.basename(file))
+      }),
+    )
 
-    await codeServerPage.openFile(file)
+    // Open a file in the latest instance.
+    await codeServerPage.openFile(files[0])
+    await codeServerPage.stateFlush()
 
-    // If we reload now VS Code will be unable to save the state changes so wait
-    // until those have been written to the database.  It flushes every five
-    // seconds so we need to wait at least that long.
-    await codeServerPage.page.waitForTimeout(5500)
+    // Open a file in an older version of code-server.  It should not see the
+    // file opened in the new instance since the database has a different
+    // name.  This must be accessed through the proxy so it shares the same
+    // domain and can write to the same database.
+    const cs = await spawn("4.0.2", dir)
+    const address = new URL(await cs.address())
+    await codeServerPage.navigate("/proxy/" + address.port + "/")
+    await codeServerPage.openFile(files[1])
+    expect(await codeServerPage.tabIsVisible(files[0])).toBe(false)
+    await codeServerPage.stateFlush()
 
-    // The tab should re-open on refresh.
-    await codeServerPage.page.reload()
-    await codeServerPage.waitForTab(file)
+    // Move back to latest code-server.  We should see the file we previously
+    // opened with it but not the old code-server file because the new instance
+    // already created its own database on this path and will avoid migrating.
+    await codeServerPage.navigate()
+    await codeServerPage.waitForTab(files[0])
+    expect(await codeServerPage.tabIsVisible(files[1])).toBe(false)
 
-    // The tab should not re-open on a different path.
-    await codeServerPage.setup(true, "/vscode")
-    expect(await codeServerPage.tabIsVisible(file)).toBe(false)
+    // Open a new path in latest code-server.  This one should migrate the
+    // database from old code-server but see nothing from the new database
+    // created on the root.
+    await codeServerPage.navigate("/vscode")
+    await codeServerPage.waitForTab(files[1])
+    expect(await codeServerPage.tabIsVisible(files[0])).toBe(false)
+    // Should still be open after a reload.
+    await codeServerPage.navigate("/vscode")
+    await codeServerPage.waitForTab(files[1])
+    expect(await codeServerPage.tabIsVisible(files[0])).toBe(false)
   })
 })
diff --git a/test/e2e/models/CodeServer.ts b/test/e2e/models/CodeServer.ts
index f6c55cb67..004fd99f0 100644
--- a/test/e2e/models/CodeServer.ts
+++ b/test/e2e/models/CodeServer.ts
@@ -3,7 +3,7 @@ import * as cp from "child_process"
 import { promises as fs } from "fs"
 import * as path from "path"
 import { Page } from "playwright"
-import util from "util"
+import * as util from "util"
 import { logError, plural } from "../../../src/common/util"
 import { onLine } from "../../../src/node/util"
 import { PASSWORD, workspaceDir } from "../../utils/constants"
@@ -38,12 +38,13 @@ export class CodeServer {
   private process: Promise<CodeServerProcess> | undefined
   public readonly logger: Logger
   private closed = false
-  private _workspaceDir: Promise<string> | undefined
 
   constructor(
     name: string,
-    private readonly codeServerArgs: string[],
-    private readonly codeServerEnv: NodeJS.ProcessEnv,
+    private readonly args: string[],
+    private readonly env: NodeJS.ProcessEnv,
+    private readonly _workspaceDir: Promise<string> | string | undefined,
+    private readonly entry = process.env.CODE_SERVER_TEST_ENTRY || ".",
   ) {
     this.logger = logger.named(name)
   }
@@ -75,7 +76,7 @@ export class CodeServer {
    */
   private async createWorkspace(): Promise<string> {
     const dir = await this.workspaceDir
-    await fs.mkdir(path.join(dir, "User"))
+    await fs.mkdir(path.join(dir, "User"), { recursive: true })
     await fs.writeFile(
       path.join(dir, "User/settings.json"),
       JSON.stringify({
@@ -96,36 +97,33 @@ export class CodeServer {
     const dir = await this.createWorkspace()
 
     return new Promise((resolve, reject) => {
-      this.logger.debug("spawning")
-      const proc = cp.spawn(
-        "node",
-        [
-          process.env.CODE_SERVER_TEST_ENTRY || ".",
-          "--extensions-dir",
-          path.join(dir, "extensions"),
-          ...this.codeServerArgs,
-          // Using port zero will spawn on a random port.
-          "--bind-addr",
-          "127.0.0.1:0",
-          // Setting the XDG variables would be easier and more thorough but the
-          // modules we import ignores those variables for non-Linux operating
-          // systems so use these flags instead.
-          "--config",
-          path.join(dir, "config.yaml"),
-          "--user-data-dir",
-          dir,
-          // The last argument is the workspace to open.
-          dir,
-        ],
-        {
-          cwd: path.join(__dirname, "../../.."),
-          env: {
-            ...process.env,
-            ...this.codeServerEnv,
-            PASSWORD,
-          },
+      const args = [
+        this.entry,
+        "--extensions-dir",
+        path.join(dir, "extensions"),
+        ...this.args,
+        // Using port zero will spawn on a random port.
+        "--bind-addr",
+        "127.0.0.1:0",
+        // Setting the XDG variables would be easier and more thorough but the
+        // modules we import ignores those variables for non-Linux operating
+        // systems so use these flags instead.
+        "--config",
+        path.join(dir, "config.yaml"),
+        "--user-data-dir",
+        dir,
+        // The last argument is the workspace to open.
+        dir,
+      ]
+      this.logger.debug("spawning `node " + args.join(" ") + "`")
+      const proc = cp.spawn("node", args, {
+        cwd: path.join(__dirname, "../../.."),
+        env: {
+          ...process.env,
+          ...this.env,
+          PASSWORD,
         },
-      )
+      })
 
       const timer = idleTimer("Failed to extract address; did the format change?", reject)
 
@@ -136,7 +134,7 @@ export class CodeServer {
       })
 
       proc.on("close", (code) => {
-        const error = new Error("closed unexpectedly")
+        const error = new Error("code-server closed unexpectedly")
         if (!this.closed) {
           this.logger.error(error.message, field("code", code))
         }
@@ -153,7 +151,7 @@ export class CodeServer {
         timer.reset()
 
         // Log the line without the timestamp.
-        this.logger.trace(line.replace(/\[.+\]/, ""))
+        this.logger.debug(line.replace(/\[.+\]/, ""))
         if (resolved) {
           return
         }
@@ -194,7 +192,11 @@ export class CodeServer {
 export class CodeServerPage {
   private readonly editorSelector = "div.monaco-workbench"
 
-  constructor(private readonly codeServer: CodeServer, public readonly page: Page) {
+  constructor(
+    private readonly codeServer: CodeServer,
+    public readonly page: Page,
+    private readonly authenticated: boolean,
+  ) {
     this.page.on("console", (message) => {
       this.codeServer.logger.debug(message)
     })
@@ -215,11 +217,18 @@ export class CodeServerPage {
   }
 
   /**
-   * Navigate to a code-server endpoint.  By default go to the root.
+   * Navigate to a code-server endpoint (root by default).  Then wait for the
+   * editor to become available.
    */
   async navigate(endpoint = "/") {
     const to = new URL(endpoint, await this.codeServer.address())
     await this.page.goto(to.toString(), { waitUntil: "networkidle" })
+
+    // Only reload editor if authenticated. Otherwise we'll get stuck
+    // reloading the login page.
+    if (this.authenticated) {
+      await this.reloadUntilEditorIsReady()
+    }
   }
 
   /**
@@ -456,21 +465,7 @@ export class CodeServerPage {
   }
 
   /**
-   * Navigates to code-server then reloads until the editor is ready.
-   *
-   * It is recommended to run setup before using this model in any tests.
-   */
-  async setup(authenticated: boolean, endpoint = "/") {
-    await this.navigate(endpoint)
-    // If we aren't authenticated we'll see a login page so we can't wait until
-    // the editor is ready.
-    if (authenticated) {
-      await this.reloadUntilEditorIsReady()
-    }
-  }
-
-  /**
-   * Execute a command in t root of the instance's workspace directory.
+   * Execute a command in the root of the instance's workspace directory.
    */
   async exec(command: string): Promise<void> {
     await util.promisify(cp.exec)(command, {
@@ -488,4 +483,15 @@ export class CodeServerPage {
       cwd: path.join(__dirname, "../../.."),
     })
   }
+
+  /**
+   * Wait for state to be flushed to the database.
+   */
+  async stateFlush(): Promise<void> {
+    // If we reload too quickly VS Code will be unable to save the state changes
+    // so wait until those have been written to the database.  It flushes every
+    // five seconds so we need to wait at least that long.
+    // TODO@asher: There must be a better way.
+    await this.page.waitForTimeout(5500)
+  }
 }
diff --git a/vendor/package.json b/vendor/package.json
index 9d00927be..86f905adf 100644
--- a/vendor/package.json
+++ b/vendor/package.json
@@ -7,6 +7,6 @@
     "postinstall": "./postinstall.sh"
   },
   "devDependencies": {
-    "code-oss-dev": "coder/vscode#bd734e3d9f21b1bce4dabab2514177e90c090ee6"
+    "code-oss-dev": "coder/vscode#94384412221f432c15bb679315c49964925090be"
   }
 }
diff --git a/vendor/yarn.lock b/vendor/yarn.lock
index 9a5eff2e1..14b8b6f42 100644
--- a/vendor/yarn.lock
+++ b/vendor/yarn.lock
@@ -274,9 +274,9 @@ clone-response@^1.0.2:
   dependencies:
     mimic-response "^1.0.0"
 
-code-oss-dev@coder/vscode#bd734e3d9f21b1bce4dabab2514177e90c090ee6:
+code-oss-dev@coder/vscode#94384412221f432c15bb679315c49964925090be:
   version "1.63.0"
-  resolved "https://codeload.github.com/coder/vscode/tar.gz/bd734e3d9f21b1bce4dabab2514177e90c090ee6"
+  resolved "https://codeload.github.com/coder/vscode/tar.gz/94384412221f432c15bb679315c49964925090be"
   dependencies:
     "@microsoft/applicationinsights-web" "^2.6.4"
     "@parcel/watcher" "2.0.3"