diff --git a/src/router.ts b/src/router.ts
index 34e85bcdbd7..c3c982b1135 100644
--- a/src/router.ts
+++ b/src/router.ts
@@ -145,6 +145,7 @@ export function pathToPattern(path: string): string {
 
   let route = "";
 
+  let nonOptionalSegments = 0;
   for (let i = 0; i < parts.length; i++) {
     const part = parts[i];
 
@@ -217,7 +218,12 @@ export function pathToPattern(path: string): string {
       }
     }
 
-    route += (optional ? "" : "/") + pattern;
+    if (optional) {
+      route += pattern;
+    } else {
+      nonOptionalSegments++;
+      route += "/" + pattern;
+    }
   }
 
   // Case: /(group)/index.tsx
@@ -225,5 +231,15 @@ export function pathToPattern(path: string): string {
     route = "/";
   }
 
+  // Handles all cases where a route starts with
+  // an optional parameter and does not contain
+  // any non-group and non-optional segments after
+  // Case: /[[id]].tsx
+  // Case: /(group)/[[id]].tsx
+  // Case: /(group)/[[name]]/(group2)/index.tsx
+  if (route.startsWith(`{/`) && nonOptionalSegments === 0) {
+    route = route.replace("{/", "/{");
+  }
+
   return route;
 }
diff --git a/src/router_test.ts b/src/router_test.ts
index 97addf3c0f7..80fcd72e05b 100644
--- a/src/router_test.ts
+++ b/src/router_test.ts
@@ -163,6 +163,11 @@ Deno.test("pathToPattern", async (t) => {
     ).toEqual(
       "/foo{/:name}?/bar{/:bob}?",
     );
+    expect(
+      pathToPattern("(group)/[[name]]/(group2)/index"),
+    ).toEqual(
+      "/{:name}?",
+    );
   });
 
   await t.step("throws on invalid patterns", () => {