diff --git a/source/main.ts b/source/main.ts
index 332b19c7..230b389c 100755
--- a/source/main.ts
+++ b/source/main.ts
@@ -76,14 +76,21 @@ if (configError || !config) {
 
 // If the user wants all the URLs rewritten to `/index.html`, make it happen.
 if (args['--single']) {
+  const singleFile = args['--single-file'];
+  let destination = '/index.html';
+
+  if (singleFile && singleFile.length > 0) {
+    destination = singleFile.startsWith('/') ? singleFile : `/${singleFile}`;
+  }
+
   const { rewrites } = config;
   const existingRewrites = Array.isArray(rewrites) ? rewrites : [];
 
   // Ensure this is the first rewrite rule so it gets priority.
   config.rewrites = [
     {
-      source: '**',
-      destination: '/index.html',
+      source: '/**/:path([^/.]+)',
+      destination,
     },
     ...existingRewrites,
   ];
diff --git a/source/types.ts b/source/types.ts
index 9294d7c3..d1565257 100644
--- a/source/types.ts
+++ b/source/types.ts
@@ -73,6 +73,7 @@ export declare interface Options {
   '--version': boolean;
   '--listen': ParsedEndpoint[];
   '--single': boolean;
+  '--single-file': string;
   '--debug': boolean;
   '--config': Path;
   '--no-request-logging': boolean;
diff --git a/source/utilities/cli.ts b/source/utilities/cli.ts
index 726c5268..7c3eb9e0 100644
--- a/source/utilities/cli.ts
+++ b/source/utilities/cli.ts
@@ -40,6 +40,8 @@ const helpText = chalkTemplate`
 
     -s, --single                        Rewrite all not-found requests to \`index.html\`
 
+    --single-file                      Rewrite all not-found requests to custom page (default: index.html)
+
     -d, --debug                         Show debugging information
 
     -c, --config                        Specify custom path to \`serve.json\`
@@ -148,6 +150,7 @@ const options = {
   '--version': Boolean,
   '--listen': [parseEndpoint] as [typeof parseEndpoint],
   '--single': Boolean,
+  '--single-file': String,
   '--debug': Boolean,
   '--config': String,
   '--no-clipboard': Boolean,
diff --git a/tests/__fixtures__/server/app/bundle.js b/tests/__fixtures__/server/app/bundle.js
new file mode 100644
index 00000000..a1983a84
--- /dev/null
+++ b/tests/__fixtures__/server/app/bundle.js
@@ -0,0 +1 @@
+console.log('bundle');
diff --git a/tests/__snapshots__/cli.test.ts.snap b/tests/__snapshots__/cli.test.ts.snap
index 9cddf0e0..a470d5f6 100644
--- a/tests/__snapshots__/cli.test.ts.snap
+++ b/tests/__snapshots__/cli.test.ts.snap
@@ -29,6 +29,8 @@ exports[`utilities/cli > render help text 1`] = `
 
     -s, --single                        Rewrite all not-found requests to \`index.html\`
 
+    --single-file                      Rewrite all not-found requests to custom page (default: index.html)
+
     -d, --debug                         Show debugging information
 
     -c, --config                        Specify custom path to \`serve.json\`
diff --git a/tests/cli.test.ts b/tests/cli.test.ts
index 21ba189a..aa78200a 100644
--- a/tests/cli.test.ts
+++ b/tests/cli.test.ts
@@ -9,6 +9,7 @@ import {
   getHelpText,
   parseEndpoint,
   checkForUpdates,
+  parseArguments,
 } from '../source/utilities/cli.js';
 import { logger } from '../source/utilities/logger.js';
 import { ParsedEndpoint } from '../source/types.js';
@@ -42,6 +43,22 @@ describe('utilities/cli', () => {
   // message, then make sure to run `vitest` with the `--update-snapshot` flag.
   test('render help text', () => expect(getHelpText()).toMatchSnapshot());
 
+  // Make sure we can set a custom fallback file when using single-page mode.
+  test('parse single-file option', () => {
+    const originalArguments = process.argv;
+
+    try {
+      process.argv = ['node', 'test', '-s', '--single-file', '_shell.html'];
+
+      const args = parseArguments();
+
+      expect(args['--single']).toBe(true);
+      expect(args['--single-file']).toBe('_shell.html');
+    } finally {
+      process.argv = originalArguments;
+    }
+  });
+
   // Make sure the `parseEndpoint` function parses valid endpoints correctly.
   test.each(validEndpoints)(
     'parse %s as endpoint',
diff --git a/tests/server.test.ts b/tests/server.test.ts
index 3656bd31..e85af5db 100644
--- a/tests/server.test.ts
+++ b/tests/server.test.ts
@@ -97,4 +97,34 @@ describe('utilities/server', () => {
 
     expect(consoleSpy).not.toHaveBeenCalled();
   });
+
+  test('rewrite extensionless routes to index when single-page rewrites are set', async () => {
+    const configWithSingle = {
+      ...config,
+      rewrites: [{ source: '/**/:path([^/.]+)', destination: '/index.html' }],
+    };
+
+    const address = await startServer({ port: 3005 }, configWithSingle, {});
+    const response = await fetch(`${address.local!}/users/settings`);
+
+    expect(response.statusCode).toBe(200);
+    expect(response.body).toContain('Hello there!');
+  });
+
+  test('do not rewrite dotted request paths when single-page rewrites are set', async () => {
+    const configWithSingle = {
+      ...config,
+      rewrites: [{ source: '/**/:path([^/.]+)', destination: '/index.html' }],
+    };
+
+    const address = await startServer({ port: 3006 }, configWithSingle, {});
+    const extensionResponse = await fetch(`${address.local!}/bundle.js`);
+    const missingExtensionResponse = await fetch(
+      `${address.local!}/does-not-exist.js`,
+    );
+
+    expect(extensionResponse.statusCode).toBe(200);
+    expect(extensionResponse.body.trimEnd()).toBe("console.log('bundle');");
+    expect(missingExtensionResponse.statusCode).toBe(404);
+  });
 });