diff --git a/.changeset/bright-insects-peel.md b/.changeset/bright-insects-peel.md
new file mode 100644
index 000000000000..69a1213cbfbc
--- /dev/null
+++ b/.changeset/bright-insects-peel.md
@@ -0,0 +1,5 @@
+---
+'astro': patch
+---
+
+Harden the limits on the number of decoding on the URL.
diff --git a/packages/astro/src/core/fetch/fetch-state.ts b/packages/astro/src/core/fetch/fetch-state.ts
index 816dc94758f3..b0dc5b79163d 100644
--- a/packages/astro/src/core/fetch/fetch-state.ts
+++ b/packages/astro/src/core/fetch/fetch-state.ts
@@ -35,7 +35,7 @@ import { getParams, getProps } from '../render/index.js';
 import { Rewrites } from '../rewrites/handler.js';
 import { isRoute404or500, isRouteServerIsland } from '../routing/match.js';
 import { normalizeUrl } from '../util/normalized-url.js';
-import { validateAndDecodePathname } from '../util/pathname.js';
+import { MultiLevelEncodingError, validateAndDecodePathname } from '../util/pathname.js';
 import { getOriginPathname, setOriginPathname } from '../routing/rewrite.js';
 import { computePathnameFromDomain } from '../i18n/domain.js';
 import { getCustom404Route, routeHasHtmlExtension } from '../routing/helpers.js';
@@ -170,6 +170,12 @@ export class FetchState implements AstroFetchState {
 	status = 200;
 	/** Whether user middleware should be skipped for this request. */
 	skipMiddleware = false;
+	/**
+	 * Set to `true` when the request path was encoded too many times to fully
+	 * decode (see {@link validateAndDecodePathname}). These requests are
+	 * rejected with a `400` before middleware or routing run.
+	 */
+	invalidEncoding = false;
 	/** A flag that tells the render content if the rewriting was triggered. */
 	isRewriting = false;
 	/** A safety net in case of loops (rewrite counter). */
@@ -915,6 +921,13 @@ export class FetchState implements AstroFetchState {
 		try {
 			return validateAndDecodePathname(pathname);
 		} catch (e: any) {
+			// The path was encoded too many times to fully decode. Mark it so
+			// the handler can reject the request with a 400 before middleware
+			// or routing run, instead of working with a half-decoded path.
+			if (e instanceof MultiLevelEncodingError) {
+				this.invalidEncoding = true;
+				return pathname;
+			}
 			this.pipeline.logger.error(null, e.toString());
 			return pathname;
 		}
diff --git a/packages/astro/src/core/i18n/handler.ts b/packages/astro/src/core/i18n/handler.ts
index e798c7fde7e3..7574029b9b2e 100644
--- a/packages/astro/src/core/i18n/handler.ts
+++ b/packages/astro/src/core/i18n/handler.ts
@@ -70,7 +70,9 @@ export class I18n {
 			return response;
 		}
 
-		const url = new URL(state.request.url);
+		// Use Astro's already-decoded URL (`state.url`) instead of reading the
+		// raw request URL again, so locale checks use the same path as routing.
+		const url = state.url;
 		const currentLocale = state.computeCurrentLocale();
 		const isPrerendered = state.routeData!.prerender;
 
diff --git a/packages/astro/src/core/routing/handler.ts b/packages/astro/src/core/routing/handler.ts
index c900921908a8..84f3d4aa3c5e 100644
--- a/packages/astro/src/core/routing/handler.ts
+++ b/packages/astro/src/core/routing/handler.ts
@@ -73,6 +73,14 @@ export class AstroHandler {
 		// forget to include anything.
 		state.pipeline.usedFeatures |= ALL_PIPELINE_FEATURES;
 
+		// Reject paths that were encoded too many times to fully decode, before
+		// any routing or middleware runs. If we let them through, middleware
+		// could check one path while a later decode turns it into a different
+		// route.
+		if (state.invalidEncoding) {
+			return new Response(null, { status: 400, statusText: 'Bad Request' });
+		}
+
 		const trailingSlashRedirect = this.#trailingSlashHandler.handle(state);
 		if (trailingSlashRedirect) {
 			return trailingSlashRedirect;
diff --git a/packages/astro/src/core/routing/rewrite.ts b/packages/astro/src/core/routing/rewrite.ts
index 6f4f3e5516fb..07790e28cc5a 100644
--- a/packages/astro/src/core/routing/rewrite.ts
+++ b/packages/astro/src/core/routing/rewrite.ts
@@ -14,6 +14,7 @@ import {
 	trimSlashes,
 } from '../path.js';
 import { createRequest } from '../request.js';
+import { validateAndDecodePathname } from '../util/pathname.js';
 import { DEFAULT_404_ROUTE } from './internal/astro-designed-error-pages.js';
 import { isRoute404, isRoute500 } from './internal/route-errors.js';
 
@@ -64,7 +65,13 @@ export function findRouteToRewrite({
 	);
 	newUrl.pathname = resolvedUrlPathname;
 
-	const decodedPathname = decodeURI(pathname);
+	// Decode the path the same way the first route match did (see
+	// `validateAndDecodePathname`) instead of calling `decodeURI` once here.
+	// Routing has to use the exact same path that middleware checked; decoding
+	// one extra time here is what let an encoded path slip past middleware and
+	// still reach a protected route. For an already-decoded path this changes
+	// nothing.
+	const decodedPathname = validateAndDecodePathname(pathname);
 
 	// Error pages (404/500) take precedence over dynamic routes that might
 	// capture the same path (e.g. [locale] matching /404). See #15098.
diff --git a/packages/astro/src/core/util/pathname.ts b/packages/astro/src/core/util/pathname.ts
index cf78d09973a7..8885f3bd8a70 100644
--- a/packages/astro/src/core/util/pathname.ts
+++ b/packages/astro/src/core/util/pathname.ts
@@ -1,30 +1,40 @@
 /**
- * Error thrown when multi-level URL encoding is detected in a pathname.
- * This is a distinct error type so callers can handle it specifically
- * (e.g., returning a 400 response) rather than falling back to partial decoding.
- *
- * @deprecated No longer thrown internally — multi-level encoding is now
- * decoded iteratively instead of rejected. Kept for backwards compatibility
- * in case third-party code references the class.
+ * Thrown when a URL path is encoded so many times that we give up decoding it
+ * (see {@link validateAndDecodePathname}). When this happens we reject the
+ * request with a `400` instead of guessing the path. If we let a half-decoded
+ * path through, your middleware might check one path while Astro routes to a
+ * different one.
  */
 export class MultiLevelEncodingError extends Error {
 	constructor() {
-		super('Multi-level URL encoding is not allowed');
+		super('URL encoding depth exceeded the maximum number of decode iterations');
 		this.name = 'MultiLevelEncodingError';
 	}
 }
 
 /**
- * Decodes a pathname iteratively until stable, collapsing all levels of
- * percent-encoding into a single canonical form. This prevents
- * double/triple encoding from bypassing middleware authorization checks
- * (CVE-2025-66202) — instead of rejecting multi-level encoding, we
- * fully resolve it so middleware always sees the true decoded path.
+ * How many times {@link validateAndDecodePathname} will decode a path before
+ * giving up. A normal URL is encoded once, or at most twice — for example a
+ * `[` (`%5B`) can arrive as `%255B` when a link is built from a value that was
+ * already encoded. A path that is still encoded after this many tries is
+ * almost certainly an attack, so we reject it instead of decoding again.
+ */
+const MAX_DECODE_ITERATIONS = 10;
+
+/**
+ * Decodes a URL path over and over until it stops changing, so a path that was
+ * encoded several times ends up as a single, final path. This stops someone
+ * from sneaking a path like `/admin` past middleware by encoding it multiple
+ * times — middleware always sees the real, decoded path.
  *
- * @param pathname - The pathname to decode
- * @returns The fully decoded pathname
- * @throws Error if the pathname contains invalid URL encoding that
- *   cannot be decoded at all (e.g., a bare `%` not followed by hex digits)
+ * @param pathname - The path to decode
+ * @returns The final, fully decoded path
+ * @throws Error if the path has broken encoding that can't be decoded at all
+ *   (for example a lone `%` that isn't followed by two hex digits)
+ * @throws MultiLevelEncodingError if the path is still changing after
+ *   {@link MAX_DECODE_ITERATIONS} tries (it was encoded too many times).
+ *   Handing back a half-decoded path here would bring back the security hole
+ *   this function exists to close.
  */
 export function validateAndDecodePathname(pathname: string): string {
 	let decoded: string;
@@ -33,21 +43,28 @@ export function validateAndDecodePathname(pathname: string): string {
 	} catch (_e) {
 		throw new Error('Invalid URL encoding');
 	}
-	// Iteratively decode until stable. Multi-level encoding (e.g.,
-	// %2561 → %61 → a) is resolved completely so that downstream code
-	// — especially middleware auth checks — always sees the canonical
-	// pathname regardless of how many encoding layers the client used.
-	// We cap iterations to prevent infinite loops on pathological input.
+	// Keep decoding until the path stops changing. A path can be encoded more
+	// than once (for example %2561 → %61 → a), and we want the final decoded
+	// path so the rest of Astro — especially middleware security checks —
+	// always sees the same real path, no matter how many times it was encoded.
 	let iterations = 0;
-	while (decoded !== pathname && iterations < 10) {
+	while (decoded !== pathname) {
+		// The path is still changing after the maximum number of tries, so it
+		// was encoded too many times for us to fully decode. Stop and reject
+		// it: handing back a half-decoded path could let middleware check one
+		// path while a later decode (during rewrite routing) turns it into a
+		// different, possibly protected, path.
+		if (iterations >= MAX_DECODE_ITERATIONS) {
+			throw new MultiLevelEncodingError();
+		}
 		pathname = decoded;
 		try {
 			decoded = decodeURI(pathname);
 		} catch {
-			// decodeURI can fail when a decoded literal '%' forms an
-			// invalid sequence with adjacent characters (e.g., '%?.pdf'
-			// after decoding %25%3F). This is fine — we've decoded as
-			// far as possible.
+			// decodeURI throws when decoding leaves a real '%' next to
+			// characters that look like broken encoding (for example '%?.pdf'
+			// after decoding %25%3F). That's fine — we've decoded as far as we
+			// can and the path won't change any further.
 			break;
 		}
 		iterations++;
diff --git a/packages/astro/test/units/app/double-encoding-bypass.test.ts b/packages/astro/test/units/app/double-encoding-bypass.test.ts
index 30e3b333cad4..54fba02c604f 100644
--- a/packages/astro/test/units/app/double-encoding-bypass.test.ts
+++ b/packages/astro/test/units/app/double-encoding-bypass.test.ts
@@ -78,6 +78,26 @@ function createAuthMiddleware() {
 	})) as () => Promise<{ onRequest: MiddlewareHandler }>;
 }
 
+/**
+ * Like {@link createAuthMiddleware}, but every allowed request is sent back
+ * through routing again with `next(context.url)`. The route it lands on must
+ * match the same path the `/api/admin` check looked at; otherwise an encoded
+ * path can slip past the check and still be decoded into `/api/admin`.
+ */
+function createRewriteAuthMiddleware() {
+	return (async () => ({
+		onRequest: (async (context, next) => {
+			if (context.url.pathname.startsWith('/api/admin')) {
+				return new Response(JSON.stringify({ error: 'Unauthorized' }), {
+					status: 401,
+					headers: { 'Content-Type': 'application/json' },
+				});
+			}
+			return next(context.url);
+		}) satisfies MiddlewareHandler,
+	})) as () => Promise<{ onRequest: MiddlewareHandler }>;
+}
+
 function createApp(middleware: ReturnType<typeof createAuthMiddleware>) {
 	return new App(
 		createManifest({
@@ -233,3 +253,48 @@ describe('URL normalization: double-encoding middleware bypass', () => {
 	});
 	// #endregion
 });
+
+describe('URL normalization: rewrite-based middleware bypass', () => {
+	it('blocks /api/admin even when middleware calls next(context.url)', async () => {
+		const app = createApp(createRewriteAuthMiddleware());
+		const response = await app.render(new Request('http://example.com/api/admin'));
+		assert.equal(response.status, 401, '/api/admin must be blocked by middleware');
+	});
+
+	it('blocks double-encoded /api/%2561dmin with a rewriting middleware', async () => {
+		// This decodes to /api/admin, so middleware must see /api/admin and
+		// block it, even though the request is then sent back through routing.
+		const app = createApp(createRewriteAuthMiddleware());
+		const response = await app.render(new Request('http://example.com/api/%2561dmin'));
+		assert.equal(
+			response.status,
+			401,
+			'double-encoded /api/admin must be blocked even with a rewriting middleware',
+		);
+	});
+
+	it('rejects an over-encoded path with 400 instead of bypassing to /api/admin', async () => {
+		// Encoded more times than we decode.
+		const app = createApp(createRewriteAuthMiddleware());
+		const response = await app.render(
+			new Request('http://example.com/api/%2525252525252525252561dmin'),
+		);
+		assert.equal(response.status, 400, 'over-encoded path must be rejected, not served');
+	});
+
+	it('rejects a deeply over-encoded payload with 400', async () => {
+		const app = createApp(createRewriteAuthMiddleware());
+		const response = await app.render(
+			new Request('http://example.com/api/%252525252525252525252561dmin'),
+		);
+		assert.equal(response.status, 400);
+	});
+
+	it('still serves non-protected routes through the rewriting middleware', async () => {
+		const app = createApp(createRewriteAuthMiddleware());
+		const response = await app.render(new Request('http://example.com/api/public/data'));
+		assert.equal(response.status, 200, '/api/public/data should be accessible');
+		const body = await response.json();
+		assert.equal(body.path, 'public/data');
+	});
+});
diff --git a/packages/astro/test/units/util/validate-and-decode-pathname.test.ts b/packages/astro/test/units/util/validate-and-decode-pathname.test.ts
index 713876a1a28d..1c6be6c62dda 100644
--- a/packages/astro/test/units/util/validate-and-decode-pathname.test.ts
+++ b/packages/astro/test/units/util/validate-and-decode-pathname.test.ts
@@ -1,6 +1,9 @@
 import assert from 'node:assert/strict';
 import { describe, it } from 'node:test';
-import { validateAndDecodePathname } from '../../../dist/core/util/pathname.js';
+import {
+	MultiLevelEncodingError,
+	validateAndDecodePathname,
+} from '../../../dist/core/util/pathname.js';
 
 describe('validateAndDecodePathname', () => {
 	// #region Plain paths (no encoding)
@@ -33,7 +36,7 @@ describe('validateAndDecodePathname', () => {
 	//
 	// Multi-level encoding is decoded iteratively until stable. This
 	// ensures middleware always sees the canonical path and can make
-	// correct authorization decisions (CVE-2025-66202 mitigation).
+	// correct authorization decisions.
 
 	it('fully decodes double-encoded unreserved chars: %2561 (a)', () => {
 		// %2561 → decodeURI → %61 → decodeURI → a
@@ -187,4 +190,39 @@ describe('validateAndDecodePathname', () => {
 		);
 	});
 	// #endregion
+	// #region Encoded too many times (rejected, must throw)
+	//
+	// If a path is still encoded after the maximum number of decode tries, we
+	// can't fully decode it. Returning the half-decoded path would let
+	// middleware check one path while a later decode (during rewrite routing)
+	// turns it into a different, protected path. So we reject these instead.
+
+	it('decodes a path encoded right up to the limit (10 times)', () => {
+		// Encoded 10 times — the most we allow — still decodes fully.
+		assert.equal(validateAndDecodePathname('/api/%25252525252525252561dmin'), '/api/admin');
+	});
+
+	it('throws MultiLevelEncodingError once a path is encoded past the limit (11 times)', () => {
+		assert.throws(
+			() => validateAndDecodePathname('/api/%2525252525252525252561dmin'),
+			(err: any) => {
+				assert.equal(err instanceof MultiLevelEncodingError, true);
+				return true;
+			},
+			'a path encoded past the limit must be rejected',
+		);
+	});
+
+	it('throws MultiLevelEncodingError for a path encoded many times', () => {
+		// Before the fix, this decoded only part way to `/%61dmin` and slipped
+		// past middleware.
+		assert.throws(
+			() => validateAndDecodePathname('/%252525252525252525252561dmin'),
+			(err: any) => {
+				assert.equal(err instanceof MultiLevelEncodingError, true);
+				return true;
+			},
+		);
+	});
+	// #endregion
 });