diff --git a/spring-cloud-gateway-core/src/main/java/org/springframework/cloud/gateway/filter/headers/XForwardedHeadersFilter.java b/spring-cloud-gateway-core/src/main/java/org/springframework/cloud/gateway/filter/headers/XForwardedHeadersFilter.java
index 789ba171..a5ec3a5e 100644
--- a/spring-cloud-gateway-core/src/main/java/org/springframework/cloud/gateway/filter/headers/XForwardedHeadersFilter.java
+++ b/spring-cloud-gateway-core/src/main/java/org/springframework/cloud/gateway/filter/headers/XForwardedHeadersFilter.java
@@ -242,11 +242,12 @@ public class XForwardedHeadersFilter implements HttpHeadersFilter, Ordered {
 
 						if(requestUriPath!=null && (originalUriPath.endsWith(requestUriPath))) {
 							prefix = originalUriPath.replace(requestUriPath, "");
+							if (prefix != null && prefix.length() > 0 &&
+									prefix.length() <= originalUri.getPath().length()) {
+								write(updated, X_FORWARDED_PREFIX_HEADER, prefix, isPrefixAppend());
+							}
 						}
-						if (prefix != null && prefix.length() > 0 &&
-								prefix.length() < originalUri.getPath().length()) {
-							write(updated, X_FORWARDED_PREFIX_HEADER, prefix, isPrefixAppend());
-						}
+
 					}
 				});
 			}
diff --git a/spring-cloud-gateway-core/src/test/java/org/springframework/cloud/gateway/filter/headers/XForwardedHeadersFilterTests.java b/spring-cloud-gateway-core/src/test/java/org/springframework/cloud/gateway/filter/headers/XForwardedHeadersFilterTests.java
index 31bade18..4049fe7c 100644
--- a/spring-cloud-gateway-core/src/test/java/org/springframework/cloud/gateway/filter/headers/XForwardedHeadersFilterTests.java
+++ b/spring-cloud-gateway-core/src/test/java/org/springframework/cloud/gateway/filter/headers/XForwardedHeadersFilterTests.java
@@ -20,6 +20,7 @@ package org.springframework.cloud.gateway.filter.headers;
 import java.net.InetAddress;
 import java.net.InetSocketAddress;
 import java.net.URI;
+import java.net.UnknownHostException;
 import java.util.LinkedHashSet;
 
 import org.junit.Test;
@@ -186,6 +187,29 @@ public class XForwardedHeadersFilterTests {
 		assertThat(headers.getFirst(X_FORWARDED_PREFIX_HEADER)).isEqualTo("/prefix");
 	}
 
+	@Test
+	public void prefixAddedWithoutTrailingSlash() throws Exception {
+		MockServerHttpRequest request = MockServerHttpRequest
+				.get("http://originalhost:8080/foo/bar")
+				.remoteAddress(new InetSocketAddress(InetAddress.getByName("10.0.0.1"), 80))
+				.build();
+
+		XForwardedHeadersFilter filter = new XForwardedHeadersFilter();
+		filter.setPrefixAppend(true);
+		filter.setPrefixEnabled(true);
+
+		ServerWebExchange exchange = MockServerWebExchange.from(request);
+		LinkedHashSet<URI> originalUris = new LinkedHashSet<>();
+		originalUris.add(UriComponentsBuilder.fromUriString("http://originalhost:8080/foo/bar").build().toUri());
+		exchange.getAttributes().put(GATEWAY_ORIGINAL_REQUEST_URL_ATTR, originalUris);
+		URI requestUri = UriComponentsBuilder.fromUriString("http://routedservice:8090/").build().toUri();
+		exchange.getAttributes().put(GATEWAY_REQUEST_URL_ATTR, requestUri);
+
+		HttpHeaders headers = filter.filter(request.getHeaders(), exchange);
+
+		assertThat(headers.getFirst(X_FORWARDED_PREFIX_HEADER)).isEqualTo("/foo/bar");
+	}
+
 	@Test
 	public void noPrefixToInfer() throws Exception {
 		MockServerHttpRequest request = MockServerHttpRequest