diff --git a/packages/deploy-cloudflare/test/unit/static.test.ts b/packages/deploy-cloudflare/test/unit/static.test.ts
index aa746e7ef..32a2a8bc5 100644
--- a/packages/deploy-cloudflare/test/unit/static.test.ts
+++ b/packages/deploy-cloudflare/test/unit/static.test.ts
@@ -88,6 +88,26 @@ describe('Cloudflare static deployment', () => {
     });
   });
 
+  it('writes authored html_handling instead of the default fallback', () => {
+    const root = mkdtempSync(join(tmpdir(), 'void-static-html-handling-'));
+    const configPath = join(root, 'wrangler.jsonc');
+    writeFileSync(configPath, '{}\n');
+
+    writeCloudflareStaticDeployConfig({
+      configPath,
+      name: 'site',
+      accountId: 'account-id',
+      main: 'static.mjs',
+      assetsDirectory: 'dist',
+      compatibilityDate: '2026-09-11',
+      assetConfig: { not_found_handling: '404-page', html_handling: 'drop-trailing-slash' },
+    });
+
+    expect(parseRootWranglerConfig(configPath).assets).toMatchObject({
+      html_handling: 'drop-trailing-slash',
+    });
+  });
+
   it('rejects duplicate keys before an edit can silently target the wrong member', () => {
     const root = mkdtempSync(join(tmpdir(), 'void-static-duplicate-'));
     const configPath = join(root, 'wrangler.jsonc');
diff --git a/packages/void/src/cli/deploy-cloudflare-static.ts b/packages/void/src/cli/deploy-cloudflare-static.ts
index d6bd48da1..65523610e 100644
--- a/packages/void/src/cli/deploy-cloudflare-static.ts
+++ b/packages/void/src/cli/deploy-cloudflare-static.ts
@@ -59,7 +59,7 @@ import {
 import { type RunDeployOptions, type CloudflareDeployDeps } from './deploy-types.ts';
 import { type CliLogger } from './log-file.ts';
 import { getErrorMessage, note } from './output.ts';
-import { buildStaticManifest } from './package.ts';
+import { buildStaticManifest, readWranglerHtmlHandling } from './package.ts';
 import { detectPreset, type StaticPreset, type FrameworkPreset } from './preset.ts';
 import { deleteEnvVarCaseAware } from './provision.ts';
 import { readWranglerManagedQueueCleanupCandidates } from './wrangler.ts';
@@ -342,6 +342,7 @@ export async function runCloudflareStaticDeploy(
     redirectRules: merged.redirectRules,
     fallbackRules: merged.fallbackRules,
     notFound: voidConfig.routing?.notFound,
+    html_handling: readWranglerHtmlHandling(rootConfig),
   });
   const entryPath = join(root, '.void', 'deploy', 'cloudflare', 'static-edge.mjs');
   mkdirSync(dirname(entryPath), { recursive: true });
diff --git a/packages/void/src/cli/package.ts b/packages/void/src/cli/package.ts
index 069a79547..4a6238e65 100644
--- a/packages/void/src/cli/package.ts
+++ b/packages/void/src/cli/package.ts
@@ -640,6 +640,27 @@ export function collectWorkerFiles(workerDir: string): Map<string, Buffer> {
   return out;
 }
 
+const WRANGLER_HTML_HANDLING = new Set<AssetConfig['html_handling']>([
+  'auto-trailing-slash',
+  'force-trailing-slash',
+  'drop-trailing-slash',
+  'none',
+]);
+
+/** Read `assets.html_handling` from a materialized root Wrangler config object. */
+export function readWranglerHtmlHandling(
+  rootConfig: Record<string, unknown>,
+): AssetConfig['html_handling'] | undefined {
+  const assets = rootConfig.assets;
+  if (typeof assets !== 'object' || assets === null || Array.isArray(assets)) {
+    return undefined;
+  }
+  const value = (assets as Record<string, unknown>).html_handling;
+  return typeof value === 'string' && WRANGLER_HTML_HANDLING.has(value as AssetConfig['html_handling'])
+    ? (value as AssetConfig['html_handling'])
+    : undefined;
+}
+
 /**
  * Build a static-deploy manifest. Pure shape transformation — no I/O.
  */
@@ -651,20 +672,32 @@ export function buildStaticManifest(opts: {
   fallbackRules?: Array<DevRedirectRule>;
   /** Explicit `routing.notFound` — overrides the appType-inferred handling. */
   notFound?: NotFoundHandling;
+  /** Authored `cloudflare.assets.html_handling` from the root Wrangler config. */
+  html_handling?: AssetConfig['html_handling'];
 }): DeployManifest {
-  const { appType, hashedAssetsPrefix, headerRules, redirectRules, fallbackRules, notFound } = opts;
+  const {
+    appType,
+    hashedAssetsPrefix,
+    headerRules,
+    redirectRules,
+    fallbackRules,
+    notFound,
+    html_handling,
+  } = opts;
   const { assetConfig, fallbackRules: resolvedFallbackRules } = resolveSpaFallbackChain(
     appType,
     fallbackRules,
     notFound,
   );
+  const resolvedAssetConfig =
+    html_handling === undefined ? assetConfig : { ...assetConfig, html_handling };
 
   const manifest: DeployManifest = {
     version: 3,
     assetManifestVersion: 2,
     bindings: {},
     type: appType,
-    assetConfig,
+    assetConfig: resolvedAssetConfig,
   };
 
   if (hashedAssetsPrefix) {
diff --git a/packages/void/src/config.ts b/packages/void/src/config.ts
index dfa475d8f..3cf522fac 100644
--- a/packages/void/src/config.ts
+++ b/packages/void/src/config.ts
@@ -1,4 +1,4 @@
-import { isRecord } from '@void/deploy-core';
+import { isRecord, type AssetConfig } from '@void/deploy-core';
 import type { RewriteDestination } from 'void/routes';
 import {
   VOID_AUTH_PROVIDERS,
@@ -156,6 +156,7 @@ export type CloudflareConfig = Record<string, unknown> & {
     directory?: string;
     binding?: string;
     not_found_handling?: NotFoundHandling;
+    html_handling?: AssetConfig['html_handling'];
     run_worker_first?: boolean | Array<string>;
   }>;
   triggers?: CloudflareField<{ crons?: Array<string> }>;
diff --git a/packages/void/test/unit/cloudflare-deploy.test.ts b/packages/void/test/unit/cloudflare-deploy.test.ts
index 2b711ae10..549f5bd43 100644
--- a/packages/void/test/unit/cloudflare-deploy.test.ts
+++ b/packages/void/test/unit/cloudflare-deploy.test.ts
@@ -2680,6 +2680,38 @@ describe('runCloudflareDeploy — static, SPA, and SSG apps', () => {
     expect(trace.indexOf('postgres-migrate')).toBeLessThan(trace.indexOf('wrangler:deploy'));
   });
 
+  it('preserves authored assets.html_handling in the generated static Wrangler config', async () => {
+    const root = makeProject({
+      'package.json': JSON.stringify({ name: 'ssgapp' }),
+      'void.json': JSON.stringify({ output: 'static' }),
+      'wrangler.jsonc': JSON.stringify({
+        account_id: 'acc123',
+        assets: { html_handling: 'drop-trailing-slash' },
+      }),
+      'pages/index.vue': `<template><div>hi</div></template>`,
+      'pages/index.server.ts': `export const loader = () => ({});`,
+    });
+    const { deps, trace, exitCalls } = harness({
+      runStaticBuild: () => {
+        trace.push('static-build');
+        mkdirSync(join(root, 'dist/client'), { recursive: true });
+        writeFileSync(join(root, 'dist/client/index.html'), '<h1>Prerendered</h1>');
+      },
+    });
+
+    await runCloudflareDeploy(root, { platform: 'cloudflare' }, silentCliLog, deps);
+
+    expect(exitCalls).toEqual([]);
+    expect(trace).toEqual(['wrangler:whoami', 'static-build', 'wrangler:deploy']);
+    expect(parseRootWranglerConfig(generatedStaticConfig(root))).toMatchObject({
+      assets: {
+        directory: '../../../dist/client',
+        not_found_handling: '404-page',
+        html_handling: 'drop-trailing-slash',
+      },
+    });
+  });
+
   it('deploys a fully prerenderable output:"static" Pages app through the thin edge Worker', async () => {
     const root = makeProject({
       'package.json': JSON.stringify({ name: 'ssgapp' }),
diff --git a/packages/void/test/unit/package.test.ts b/packages/void/test/unit/package.test.ts
index 46e704f7a..85a8312a8 100644
--- a/packages/void/test/unit/package.test.ts
+++ b/packages/void/test/unit/package.test.ts
@@ -4,6 +4,7 @@ import { afterEach, beforeEach, describe, expect, it } from 'vite-plus/test';
 import {
   buildFrameworkManifest,
   buildStaticManifest,
+  readWranglerHtmlHandling,
   buildVoidManifest,
   computeAssetHash,
   collectAndHashAssets,
@@ -315,6 +316,30 @@ describe('buildStaticManifest', () => {
       { source: '/docs/*', destination: '/docs.html', status: 200 },
     ]);
   });
+
+  it('carries authored html_handling into assetConfig', () => {
+    expect(
+      buildStaticManifest({ appType: 'static', html_handling: 'drop-trailing-slash' }).assetConfig,
+    ).toEqual({
+      not_found_handling: '404-page',
+      html_handling: 'drop-trailing-slash',
+    });
+  });
+});
+
+describe('readWranglerHtmlHandling', () => {
+  it('reads a supported assets.html_handling value', () => {
+    expect(
+      readWranglerHtmlHandling({
+        assets: { html_handling: 'drop-trailing-slash' },
+      }),
+    ).toBe('drop-trailing-slash');
+  });
+
+  it('ignores missing or invalid values', () => {
+    expect(readWranglerHtmlHandling({})).toBeUndefined();
+    expect(readWranglerHtmlHandling({ assets: { html_handling: 'bogus' } })).toBeUndefined();
+  });
 });
 
 describe('collectAndHashAssets', () => {