diff --git a/spring-web/src/main/java/org/springframework/web/filter/UrlHandlerFilter.java b/spring-web/src/main/java/org/springframework/web/filter/UrlHandlerFilter.java
index ef805b2bf1..905fbaafa4 100644
--- a/spring-web/src/main/java/org/springframework/web/filter/UrlHandlerFilter.java
+++ b/spring-web/src/main/java/org/springframework/web/filter/UrlHandlerFilter.java
@@ -278,7 +278,7 @@ public final class UrlHandlerFilter extends OncePerRequestFilter {
 
 		@Override
 		public boolean canHandle(HttpServletRequest request, RequestPath path) {
-			List<PathContainer.Element> elements = path.elements();
+			List<PathContainer.Element> elements = path.pathWithinApplication().elements();
 			return (elements.size() > 1 && elements.get(elements.size() - 1).value().equals("/"));
 		}
 
diff --git a/spring-web/src/main/java/org/springframework/web/filter/reactive/UrlHandlerFilter.java b/spring-web/src/main/java/org/springframework/web/filter/reactive/UrlHandlerFilter.java
index 5d1d2c62f0..d76bffcee7 100644
--- a/spring-web/src/main/java/org/springframework/web/filter/reactive/UrlHandlerFilter.java
+++ b/spring-web/src/main/java/org/springframework/web/filter/reactive/UrlHandlerFilter.java
@@ -253,7 +253,8 @@ public final class UrlHandlerFilter implements WebFilter {
 
 		@Override
 		public boolean canHandle(ServerWebExchange exchange) {
-			List<PathContainer.Element> elements = exchange.getRequest().getPath().elements();
+			ServerHttpRequest request = exchange.getRequest();
+			List<PathContainer.Element> elements = request.getPath().pathWithinApplication().elements();
 			return (elements.size() > 1 && elements.get(elements.size() - 1).value().equals("/"));
 		}
 
diff --git a/spring-web/src/test/java/org/springframework/web/filter/UrlHandlerFilterTests.java b/spring-web/src/test/java/org/springframework/web/filter/UrlHandlerFilterTests.java
index d3d1ee73bb..41a4f21555 100644
--- a/spring-web/src/test/java/org/springframework/web/filter/UrlHandlerFilterTests.java
+++ b/spring-web/src/test/java/org/springframework/web/filter/UrlHandlerFilterTests.java
@@ -87,17 +87,20 @@ public class UrlHandlerFilterTests {
 
 	@Test
 	void noUrlHandling() throws Exception {
-		testNoUrlHandling("/path/**", "/path/123");
-		testNoUrlHandling("/path/*", "/path/123");
-		testNoUrlHandling("/**", "/"); // gh-33444
+		testNoUrlHandling("/path/**", "", "/path/123");
+		testNoUrlHandling("/path/*", "", "/path/123");
+		testNoUrlHandling("/**", "", "/"); // gh-33444
+		testNoUrlHandling("/**", "/myApp", "/myApp/"); // gh-33565
 	}
 
-	private static void testNoUrlHandling(String pattern, String requestURI) throws ServletException, IOException {
+	private static void testNoUrlHandling(String pattern, String contextPath, String requestURI)
+			throws ServletException, IOException {
 
 		// No request wrapping
 		UrlHandlerFilter filter = UrlHandlerFilter.trailingSlashHandler(pattern).wrapRequest().build();
 
 		MockHttpServletRequest request = new MockHttpServletRequest("GET", requestURI);
+		request.setContextPath(contextPath);
 		MockFilterChain chain = new MockFilterChain();
 		filter.doFilterInternal(request, new MockHttpServletResponse(), chain);
 
@@ -109,6 +112,7 @@ public class UrlHandlerFilterTests {
 		filter = UrlHandlerFilter.trailingSlashHandler(pattern).redirect(status).build();
 
 		request = new MockHttpServletRequest("GET", requestURI);
+		request.setContextPath(contextPath);
 		MockHttpServletResponse response = new MockHttpServletResponse();
 
 		chain = new MockFilterChain();
diff --git a/spring-web/src/test/java/org/springframework/web/filter/reactive/UrlHandlerFilterTests.java b/spring-web/src/test/java/org/springframework/web/filter/reactive/UrlHandlerFilterTests.java
index a92f2194af..d3288302f7 100644
--- a/spring-web/src/test/java/org/springframework/web/filter/reactive/UrlHandlerFilterTests.java
+++ b/spring-web/src/test/java/org/springframework/web/filter/reactive/UrlHandlerFilterTests.java
@@ -76,17 +76,18 @@ public class UrlHandlerFilterTests {
 
 	@Test
 	void noUrlHandling() {
-		testNoUrlHandling("/path/**", "/path/123");
-		testNoUrlHandling("/path/*", "/path/123");
-		testNoUrlHandling("/**", "/"); // gh-33444
+		testNoUrlHandling("/path/**", "", "/path/123");
+		testNoUrlHandling("/path/*", "", "/path/123");
+		testNoUrlHandling("/**", "", "/"); // gh-33444
+		testNoUrlHandling("/**", "/myApp", "/myApp/"); // gh-33565
 	}
 
-	private static void testNoUrlHandling(String pattern, String path) {
+	private static void testNoUrlHandling(String pattern, String contextPath, String path) {
 
 		// No request mutation
 		UrlHandlerFilter filter = UrlHandlerFilter.trailingSlashHandler(pattern).mutateRequest().build();
 
-		MockServerHttpRequest request = MockServerHttpRequest.get(path).build();
+		MockServerHttpRequest request = MockServerHttpRequest.get(path).contextPath(contextPath).build();
 		ServerWebExchange exchange = MockServerWebExchange.from(request);
 
 		ServerHttpRequest actual = invokeFilter(filter, exchange);
@@ -98,7 +99,7 @@ public class UrlHandlerFilterTests {
 		HttpStatus status = HttpStatus.PERMANENT_REDIRECT;
 		filter = UrlHandlerFilter.trailingSlashHandler(pattern).redirect(status).build();
 
-		request = MockServerHttpRequest.get(path).build();
+		request = MockServerHttpRequest.get(path).contextPath(contextPath).build();
 		exchange = MockServerWebExchange.from(request);
 
 		actual = invokeFilter(filter, exchange);