diff --git a/spring-webmvc/src/main/java/org/springframework/web/servlet/resource/ResourceUrlProvider.java b/spring-webmvc/src/main/java/org/springframework/web/servlet/resource/ResourceUrlProvider.java
index 519526fefe..41dc298aac 100644
--- a/spring-webmvc/src/main/java/org/springframework/web/servlet/resource/ResourceUrlProvider.java
+++ b/spring-webmvc/src/main/java/org/springframework/web/servlet/resource/ResourceUrlProvider.java
@@ -180,7 +180,7 @@ public class ResourceUrlProvider implements ApplicationListener<ContextRefreshed
 		}
 
 		int index = getPathHelper().getRequestUri(request).indexOf(pathWithinMapping);
-		Assert.state(index > 0 && index < requestUrl.length(), "Failed to determine lookup path: " + requestUrl);
+		Assert.state(index != -1, "Failed to determine lookup path: " + requestUrl);
 
 		String prefix = requestUrl.substring(0, index);
 		String lookupPath = requestUrl.substring(index);
diff --git a/spring-webmvc/src/test/java/org/springframework/web/servlet/resource/ResourceTransformerSupportTests.java b/spring-webmvc/src/test/java/org/springframework/web/servlet/resource/ResourceTransformerSupportTests.java
index b9f389e406..f3f2f96082 100644
--- a/spring-webmvc/src/test/java/org/springframework/web/servlet/resource/ResourceTransformerSupportTests.java
+++ b/spring-webmvc/src/test/java/org/springframework/web/servlet/resource/ResourceTransformerSupportTests.java
@@ -73,7 +73,7 @@ public class ResourceTransformerSupportTests {
 	}
 
 	@Test
-	public void rewriteAbsolutePath() throws Exception {
+	public void rewriteAbsolutePathWithContext() throws Exception {
 		this.request.setRequestURI("/servlet/context/resources/main.css");
 		this.request.setMethod("GET");
 		this.request.setServletPath("/servlet");
@@ -84,6 +84,18 @@ public class ResourceTransformerSupportTests {
 		Resource mainCss = new ClassPathResource("test/main.css", getClass());
 		String actual = this.transformer.resolveUrlPath(resourcePath, this.request, mainCss, this.transformerChain);
 		assertEquals("/servlet/context/resources/bar-11e16cf79faee7ac698c805cf28248d2.css", actual);
+	}
+
+	@Test
+	public void rewriteAbsolutePath() throws Exception {
+		this.request.setRequestURI("/resources/main.css");
+		this.request.setMethod("GET");
+		this.request.setAttribute(HandlerMapping.PATH_WITHIN_HANDLER_MAPPING_ATTRIBUTE, "/resources/main.css");
+
+		String resourcePath = "/resources/bar.css";
+		Resource mainCss = new ClassPathResource("test/main.css", getClass());
+		String actual = this.transformer.resolveUrlPath(resourcePath, this.request, mainCss, this.transformerChain);
+		assertEquals("/resources/bar-11e16cf79faee7ac698c805cf28248d2.css", actual);
 
 		actual = this.transformer.resolveUrlPath("bar.css", this.request, mainCss, this.transformerChain);
 		assertEquals("bar-11e16cf79faee7ac698c805cf28248d2.css", actual);
@@ -102,6 +114,19 @@ public class ResourceTransformerSupportTests {
 		assertEquals("bar-11e16cf79faee7ac698c805cf28248d2.css", actual);
 	}
 
+	@Test(expected = IllegalStateException.class)
+	public void rewriteAbsolutePathWrongPath() throws Exception {
+		this.request.setRequestURI("/servlet/context/resources/main.css");
+		this.request.setMethod("GET");
+		this.request.setServletPath("/servlet");
+		this.request.setContextPath("/context");
+		this.request.setAttribute(HandlerMapping.PATH_WITHIN_HANDLER_MAPPING_ATTRIBUTE, "/wrong/main.css");
+
+		String resourcePath = "/servlet/context/resources/bar.css";
+		Resource mainCss = new ClassPathResource("test/main.css", getClass());
+		this.transformer.resolveUrlPath(resourcePath, this.request, mainCss, this.transformerChain);
+	}
+
 	@Test
 	public void rewriteRelativePathUpperLevel() throws Exception {
 		this.request.setRequestURI("/servlet/context/resources/images/image.png");