diff --git a/.changeset/sharp-cameras-rescue.md b/.changeset/sharp-cameras-rescue.md
new file mode 100644
index 00000000..bda9afe6
--- /dev/null
+++ b/.changeset/sharp-cameras-rescue.md
@@ -0,0 +1,5 @@
+---
+'@astrojs/cloudflare': patch
+---
+
+Fixes an error with automatic deduplication of `_routes.json` for more complex project structures
diff --git a/packages/cloudflare/src/utils/deduplicatePatterns.ts b/packages/cloudflare/src/utils/deduplicatePatterns.ts
index 362ac167..b408083b 100644
--- a/packages/cloudflare/src/utils/deduplicatePatterns.ts
+++ b/packages/cloudflare/src/utils/deduplicatePatterns.ts
@@ -13,7 +13,7 @@ export function deduplicatePatterns(patterns: string[]) {
 	const uniquePatterns = [...new Set(patterns)];
 	for (const pattern of uniquePatterns) {
 		if (pattern.endsWith('*')) {
-			openPatterns.push(new RegExp(`^${pattern.replace(/(\*\/)*\*$/g, '[^*\n]*$')}`));
+			openPatterns.push(new RegExp(`^${pattern.replace(/(\*\/)*\*$/g, '(?=.{2,}).+[^*\n]$')}`));
 		}
 	}
 
diff --git a/packages/cloudflare/test/routes-json.test.js b/packages/cloudflare/test/routes-json.test.js
index 8997ac4e..e9889967 100644
--- a/packages/cloudflare/test/routes-json.test.js
+++ b/packages/cloudflare/test/routes-json.test.js
@@ -202,7 +202,7 @@ describe('_routes.json generation', () => {
 						assert.deepEqual(routes, {
 							version: 1,
 							include: ['/a/*', '/_image'],
-							exclude: ['/a/*', '/another'],
+							exclude: ['/a/', '/a/*', '/another'],
 						});
 					});
 				});