diff --git a/.changeset/seven-bottles-warn.md b/.changeset/seven-bottles-warn.md
new file mode 100644
index 0000000000..653618200d
--- /dev/null
+++ b/.changeset/seven-bottles-warn.md
@@ -0,0 +1,5 @@
+---
+'astro': patch
+---
+
+Fixes dev server not stopping cleanly
diff --git a/packages/astro/src/core/dev/index.ts b/packages/astro/src/core/dev/index.ts
index 56808fd784..a7856bf332 100644
--- a/packages/astro/src/core/dev/index.ts
+++ b/packages/astro/src/core/dev/index.ts
@@ -26,7 +26,7 @@ export interface DevOptions {
   logging: LogOptions;
 }
 
-interface DevServer {
+export interface DevServer {
   hostname: string;
   port: number;
   server: connect.Server;
@@ -96,7 +96,7 @@ export class AstroDevServer {
       await this.viteServer.close();
     }
     if (this.httpServer) {
-      await promisify(this.httpServer.close)();
+      await promisify(this.httpServer.close.bind(this.httpServer))();
     }
   }
 
diff --git a/packages/astro/test/astro-styles-ssr.test.js b/packages/astro/test/astro-styles-ssr.test.js
index 168cded3e0..ad9e0b7ee9 100644
--- a/packages/astro/test/astro-styles-ssr.test.js
+++ b/packages/astro/test/astro-styles-ssr.test.js
@@ -3,7 +3,7 @@ import cheerio from 'cheerio';
 import { loadFixture } from './test-utils.js';
 
 describe('Styles SSR', function () {
-  this.timeout(5000);
+  this.timeout(10000);
 
   let fixture;
   let index$;
diff --git a/packages/astro/test/dev-routing.test.js b/packages/astro/test/dev-routing.test.js
new file mode 100644
index 0000000000..0a96aefdb4
--- /dev/null
+++ b/packages/astro/test/dev-routing.test.js
@@ -0,0 +1,129 @@
+import { expect } from 'chai';
+import cheerio from 'cheerio';
+import { loadFixture } from './test-utils.js';
+
+describe('Development Routing', () => {
+  describe('No site config', () => {
+    /** @type {import('./test-utils').Fixture} */
+    let fixture
+    /** @type {import('./test-utils').DevServer} */
+    let devServer;
+
+    before(async () => {
+      fixture = await loadFixture({ projectRoot: './fixtures/without-site-config/' });
+      devServer = await fixture.startDevServer();
+    });
+
+    after(async () => {
+      devServer && await devServer.stop();
+    });
+
+    it('200 when loading /', async () => {
+      const response = await fixture.fetch('/');
+      expect(response.status).to.equal(200);
+    });
+
+    it('200 when loading non-root page', async () => {
+      const response = await fixture.fetch('/another');
+      expect(response.status).to.equal(200);
+    })
+  });
+
+  describe('No subpath used', () => {
+    /** @type {import('./test-utils').Fixture} */
+    let fixture
+    /** @type {import('./test-utils').DevServer} */
+    let devServer;
+
+    before(async () => {
+      fixture = await loadFixture({ projectRoot: './fixtures/without-subpath/' });
+      devServer = await fixture.startDevServer();
+    });
+
+    after(async () => {
+      devServer && await devServer.stop();
+    });
+
+    it('200 when loading /', async () => {
+      const response = await fixture.fetch('/');
+      expect(response.status).to.equal(200);
+    });
+
+    it('200 when loading non-root page', async () => {
+      const response = await fixture.fetch('/another');
+      expect(response.status).to.equal(200);
+    })
+  });
+
+  describe('Subpath with trailing slash', () => {
+    /** @type {import('./test-utils').Fixture} */
+    let fixture
+    /** @type {import('./test-utils').DevServer} */
+    let devServer;
+
+    before(async () => {
+      fixture = await loadFixture({ projectRoot: './fixtures/with-subpath-trailing-slash/' });
+      devServer = await fixture.startDevServer();
+    });
+
+    after(async () => {
+      devServer && await devServer.stop();
+    });
+
+    it('404 when loading /', async () => {
+      const response = await fixture.fetch('/');
+      expect(response.status).to.equal(404);
+    });
+
+    it('200 when loading subpath root', async () => {
+      const response = await fixture.fetch('/blog/');
+      expect(response.status).to.equal(200);
+    });
+
+    it('404 when loading subpath root without trailing slash', async () => {
+      const response = await fixture.fetch('/blog');
+      expect(response.status).to.equal(404);
+    });
+
+    it('200 when loading another page with subpath used', async () => {
+      const response = await fixture.fetch('/blog/another/');
+      expect(response.status).to.equal(200);
+    });
+  });
+
+  describe('Subpath without trailing slash', () => {
+    /** @type {import('./test-utils').Fixture} */
+    let fixture
+    /** @type {import('./test-utils').DevServer} */
+    let devServer;
+
+    before(async () => {
+      fixture = await loadFixture({ projectRoot: './fixtures/with-subpath-no-trailing-slash/' });
+      devServer = await fixture.startDevServer();
+    });
+
+    after(async () => {
+      devServer && await devServer.stop();
+    });
+
+    it('404 when loading /', async () => {
+      const response = await fixture.fetch('/');
+      expect(response.status).to.equal(404);
+    });
+
+    it('200 when loading subpath root with trailing slash', async () => {
+      const response = await fixture.fetch('/blog/');
+      expect(response.status).to.equal(200);
+    });
+
+    it('200 when loading subpath root without trailing slash', async () => {
+      const response = await fixture.fetch('/blog');
+      expect(response.status).to.equal(200);
+    });
+
+    it('200 when loading another page with subpath used', async () => {
+      const response = await fixture.fetch('/blog/another/');
+      expect(response.status).to.equal(200);
+    });
+  });
+});
\ No newline at end of file
diff --git a/packages/astro/test/fixtures/with-subpath-no-trailing-slash/astro.config.mjs b/packages/astro/test/fixtures/with-subpath-no-trailing-slash/astro.config.mjs
new file mode 100644
index 0000000000..616285e2b4
--- /dev/null
+++ b/packages/astro/test/fixtures/with-subpath-no-trailing-slash/astro.config.mjs
@@ -0,0 +1,6 @@
+
+export default {
+  buildOptions: {
+    site: 'http://example.com/blog'
+  }
+}
\ No newline at end of file
diff --git a/packages/astro/test/fixtures/with-subpath-no-trailing-slash/src/pages/another.astro b/packages/astro/test/fixtures/with-subpath-no-trailing-slash/src/pages/another.astro
new file mode 100644
index 0000000000..d0563f4145
--- /dev/null
+++ b/packages/astro/test/fixtures/with-subpath-no-trailing-slash/src/pages/another.astro
@@ -0,0 +1 @@
+<div>another page</div>
\ No newline at end of file
diff --git a/packages/astro/test/fixtures/with-subpath-no-trailing-slash/src/pages/index.astro b/packages/astro/test/fixtures/with-subpath-no-trailing-slash/src/pages/index.astro
new file mode 100644
index 0000000000..42e6a51771
--- /dev/null
+++ b/packages/astro/test/fixtures/with-subpath-no-trailing-slash/src/pages/index.astro
@@ -0,0 +1 @@
+<div>testing</div>
\ No newline at end of file
diff --git a/packages/astro/test/fixtures/with-subpath-trailing-slash/astro.config.mjs b/packages/astro/test/fixtures/with-subpath-trailing-slash/astro.config.mjs
new file mode 100644
index 0000000000..5f2ab2688d
--- /dev/null
+++ b/packages/astro/test/fixtures/with-subpath-trailing-slash/astro.config.mjs
@@ -0,0 +1,6 @@
+
+export default {
+  buildOptions: {
+    site: 'http://example.com/blog/'
+  }
+}
\ No newline at end of file
diff --git a/packages/astro/test/fixtures/with-subpath-trailing-slash/src/pages/another.astro b/packages/astro/test/fixtures/with-subpath-trailing-slash/src/pages/another.astro
new file mode 100644
index 0000000000..d0563f4145
--- /dev/null
+++ b/packages/astro/test/fixtures/with-subpath-trailing-slash/src/pages/another.astro
@@ -0,0 +1 @@
+<div>another page</div>
\ No newline at end of file
diff --git a/packages/astro/test/fixtures/with-subpath-trailing-slash/src/pages/index.astro b/packages/astro/test/fixtures/with-subpath-trailing-slash/src/pages/index.astro
new file mode 100644
index 0000000000..8dca56dd88
--- /dev/null
+++ b/packages/astro/test/fixtures/with-subpath-trailing-slash/src/pages/index.astro
@@ -0,0 +1 @@
+<div>Hello world</div>
\ No newline at end of file
diff --git a/packages/astro/test/fixtures/without-site-config/src/pages/another.astro b/packages/astro/test/fixtures/without-site-config/src/pages/another.astro
new file mode 100644
index 0000000000..d0563f4145
--- /dev/null
+++ b/packages/astro/test/fixtures/without-site-config/src/pages/another.astro
@@ -0,0 +1 @@
+<div>another page</div>
\ No newline at end of file
diff --git a/packages/astro/test/fixtures/without-site-config/src/pages/index.astro b/packages/astro/test/fixtures/without-site-config/src/pages/index.astro
new file mode 100644
index 0000000000..42e6a51771
--- /dev/null
+++ b/packages/astro/test/fixtures/without-site-config/src/pages/index.astro
@@ -0,0 +1 @@
+<div>testing</div>
\ No newline at end of file
diff --git a/packages/astro/test/fixtures/without-subpath/astro.config.mjs b/packages/astro/test/fixtures/without-subpath/astro.config.mjs
new file mode 100644
index 0000000000..7ac59b3413
--- /dev/null
+++ b/packages/astro/test/fixtures/without-subpath/astro.config.mjs
@@ -0,0 +1,6 @@
+
+export default {
+  buildOptions: {
+    site: 'http://example.com/'
+  }
+}
\ No newline at end of file
diff --git a/packages/astro/test/fixtures/without-subpath/src/pages/another.astro b/packages/astro/test/fixtures/without-subpath/src/pages/another.astro
new file mode 100644
index 0000000000..d0563f4145
--- /dev/null
+++ b/packages/astro/test/fixtures/without-subpath/src/pages/another.astro
@@ -0,0 +1 @@
+<div>another page</div>
\ No newline at end of file
diff --git a/packages/astro/test/fixtures/without-subpath/src/pages/index.astro b/packages/astro/test/fixtures/without-subpath/src/pages/index.astro
new file mode 100644
index 0000000000..42e6a51771
--- /dev/null
+++ b/packages/astro/test/fixtures/without-subpath/src/pages/index.astro
@@ -0,0 +1 @@
+<div>testing</div>
\ No newline at end of file
diff --git a/packages/astro/test/test-utils.js b/packages/astro/test/test-utils.js
index d4876563da..eb282b4c79 100644
--- a/packages/astro/test/test-utils.js
+++ b/packages/astro/test/test-utils.js
@@ -3,13 +3,25 @@ import fetch from 'node-fetch';
 import fs from 'fs';
 import { fileURLToPath } from 'url';
 import { loadConfig } from '../dist/core/config.js';
+import dev from '../dist/core/dev/index.js';
 import build from '../dist/core/build/index.js';
 import preview from '../dist/core/preview/index.js';
+/**
+ * @typedef {import('node-fetch').Response} Response
+ * @typedef {import('../src/core/dev/index').DevServer} DevServer
+ *
+ *
+ * @typedef {Object} Fixture
+ * @property {typeof build} build
+ * @property {(url: string, opts: any) => Promise<Response>} fetch
+ * @property {(path: string) => Promise<string>} readFile
+ * @property {() => Promise<DevServer>} startDevServer
+ */
 
 /**
  * Load Astro fixture
  * @param {Object} inlineConfig Astro config partial (note: must specify projectRoot)
- * @returns {Object} Fixture. Has the following properties:
+ * @returns {Fixture} The fixture. Has the following properties:
  *   .config     - Returns the final config. Will be automatically passed to the methods below:
  *
  *   Build
@@ -40,6 +52,7 @@ export async function loadFixture(inlineConfig) {
 
   return {
     build: (opts = {}) => build(config, { mode: 'development', logging: 'error', ...opts }),
+    startDevServer: () => dev(config, { logging: 'error' }),
     config,
     fetch: (url, init) => fetch(`http://${config.devOptions.hostname}:${config.devOptions.port}${url.replace(/^\/?/, '/')}`, init),
     preview: async (opts = {}) => {