diff --git a/src/Path/FileMatch/FileMatch.php b/src/Path/FileMatch/FileMatch.php
index 295b6e9..5b90eae 100644
--- a/src/Path/FileMatch/FileMatch.php
+++ b/src/Path/FileMatch/FileMatch.php
@@ -73,13 +73,13 @@ protected function filterDynamicPathParts(
 		array $uriPathParts
 	):array {
 		$filePathParts = explode("/", $filePath);
-		$matchingSibling = in_array($uriPathParts, $this->siblingFilePathParts);
 
 		foreach($uriPathParts as $i => $uriPathPart) {
 			if(!isset($filePathParts[$i])) {
 				break;
 			}
 
+			$matchingSibling = in_array($uriPathParts, $this->siblingFilePathParts);
 			$filePathPart = $filePathParts[$i];
 
 // On the last iteration, don't convert if there's a sibling match.
diff --git a/test/phpunit/Path/FileMatch/BasicFileMatchTest.php b/test/phpunit/Path/FileMatch/BasicFileMatchTest.php
index d4270e8..15fbfbb 100644
--- a/test/phpunit/Path/FileMatch/BasicFileMatchTest.php
+++ b/test/phpunit/Path/FileMatch/BasicFileMatchTest.php
@@ -90,4 +90,17 @@ public function testMatches_dynamicPath_siblingMatchesIndex():void {
 		self::assertTrue($sut->matches("/request/dynamic-example"));
 		self::assertFalse($sut->matches("/request/secrets"));
 	}
+
+	public function testMatches_nestedDynamicPath_siblingMatchesIndex():void {
+		$sut = new BasicFileMatch(
+			"page/request/@share-id/@request-id.html",
+			"page",
+			[
+				"page/request/@share-id/index.html",
+				"page/request/@share-id/secrets.html",
+			]
+		);
+		self::assertTrue($sut->matches("/request/share123/dynamic-example"));
+		self::assertFalse($sut->matches("/request/share123/secrets"));
+	}
 }