diff --git a/spring-cloud-gateway-server-webmvc/src/main/java/org/springframework/cloud/gateway/server/mvc/filter/XForwardedRequestHeadersFilter.java b/spring-cloud-gateway-server-webmvc/src/main/java/org/springframework/cloud/gateway/server/mvc/filter/XForwardedRequestHeadersFilter.java
index 4ef283ca8..960575e52 100644
--- a/spring-cloud-gateway-server-webmvc/src/main/java/org/springframework/cloud/gateway/server/mvc/filter/XForwardedRequestHeadersFilter.java
+++ b/spring-cloud-gateway-server-webmvc/src/main/java/org/springframework/cloud/gateway/server/mvc/filter/XForwardedRequestHeadersFilter.java
@@ -138,20 +138,22 @@ public HttpHeaders apply(HttpHeaders input, ServerRequest request) {
 					MvcUtils.GATEWAY_ORIGINAL_REQUEST_URL_ATTR);
 			URI requestUri = request.uri();
 
-			if (originalUris != null && requestUri != null) {
+			if (originalUris != null && !originalUris.isEmpty() && requestUri != null) {
 
-				originalUris.forEach(originalUri -> {
+				// only the first uri counts: it is the url as received from the client.
+				// later entries are intermediate snapshots added by each path-mutating
+				// filter and would produce overlapping prefixes (gh-4237)
+				URI originalUri = originalUris.iterator().next();
 
-					if (originalUri != null && originalUri.getPath() != null) {
-						// strip trailing slashes before checking if request path is end
-						// of original path
-						String originalUriPath = stripTrailingSlash(originalUri);
-						String requestUriPath = stripTrailingSlash(requestUri);
+				if (originalUri != null && originalUri.getPath() != null) {
+					// strip trailing slashes before checking if request path is end
+					// of original path
+					String originalUriPath = stripTrailingSlash(originalUri);
+					String requestUriPath = stripTrailingSlash(requestUri);
 
-						updateRequest(updated, originalUri, originalUriPath, requestUriPath);
+					updateRequest(updated, originalUri, originalUriPath, requestUriPath);
 
-					}
-				});
+				}
 			}
 		}
 
diff --git a/spring-cloud-gateway-server-webmvc/src/test/java/org/springframework/cloud/gateway/server/mvc/filter/XForwardedRequestHeadersFilterTests.java b/spring-cloud-gateway-server-webmvc/src/test/java/org/springframework/cloud/gateway/server/mvc/filter/XForwardedRequestHeadersFilterTests.java
index 28846ba0a..741599033 100644
--- a/spring-cloud-gateway-server-webmvc/src/test/java/org/springframework/cloud/gateway/server/mvc/filter/XForwardedRequestHeadersFilterTests.java
+++ b/spring-cloud-gateway-server-webmvc/src/test/java/org/springframework/cloud/gateway/server/mvc/filter/XForwardedRequestHeadersFilterTests.java
@@ -16,6 +16,7 @@
 
 package org.springframework.cloud.gateway.server.mvc.filter;
 
+import java.net.URI;
 import java.util.Collections;
 
 import org.assertj.core.api.Assertions;
@@ -28,6 +29,7 @@
 import org.springframework.boot.tomcat.autoconfigure.servlet.TomcatServletWebServerAutoConfiguration;
 import org.springframework.boot.webmvc.autoconfigure.WebMvcAutoConfiguration;
 import org.springframework.cloud.gateway.server.mvc.GatewayServerMvcAutoConfiguration;
+import org.springframework.cloud.gateway.server.mvc.common.MvcUtils;
 import org.springframework.cloud.gateway.server.mvc.config.GatewayMvcProperties;
 import org.springframework.cloud.gateway.server.mvc.predicate.PredicateAutoConfiguration;
 import org.springframework.http.HttpHeaders;
@@ -39,6 +41,7 @@
 import static org.springframework.cloud.gateway.server.mvc.filter.XForwardedRequestHeadersFilter.X_FORWARDED_FOR_HEADER;
 import static org.springframework.cloud.gateway.server.mvc.filter.XForwardedRequestHeadersFilter.X_FORWARDED_HOST_HEADER;
 import static org.springframework.cloud.gateway.server.mvc.filter.XForwardedRequestHeadersFilter.X_FORWARDED_PORT_HEADER;
+import static org.springframework.cloud.gateway.server.mvc.filter.XForwardedRequestHeadersFilter.X_FORWARDED_PREFIX_HEADER;
 import static org.springframework.cloud.gateway.server.mvc.filter.XForwardedRequestHeadersFilter.X_FORWARDED_PROTO_HEADER;
 
 /**
@@ -162,4 +165,44 @@ public void remoteAdddressIsNullUnTrustedProxyNotAppended() {
 		assertThat(headers.getFirst(X_FORWARDED_FOR_HEADER)).doesNotContain("127.0.0.1");
 	}
 
+	@Test
+	public void prefixToInferOnceWhenChainedPathFiltersProcessRequest() {
+		MockHttpServletRequest servletRequest = MockMvcRequestBuilders.get("http://localhost:8080/blue")
+			.remoteAddress("10.0.0.1:80")
+			.buildRequest(null);
+		ServerRequest request = ServerRequest.create(servletRequest, Collections.emptyList());
+
+		// two chained path filters, e.g. StripPrefix=1 twice, add one entry each
+		MvcUtils.addOriginalRequestUrl(request, URI.create("http://localhost:8080/tenant/api/blue"));
+		MvcUtils.addOriginalRequestUrl(request, URI.create("http://localhost:8080/api/blue"));
+
+		XForwardedRequestHeadersFilter filter = new XForwardedRequestHeadersFilter(
+				new XForwardedRequestHeadersFilterProperties(), ".*");
+
+		HttpHeaders headers = filter.apply(request.headers().asHttpHeaders(), request);
+
+		assertThat(headers.headerNames()).contains(X_FORWARDED_PREFIX_HEADER);
+
+		assertThat(headers.getFirst(X_FORWARDED_PREFIX_HEADER)).isEqualTo("/tenant/api");
+	}
+
+	@Test
+	public void prefixAppendedToExistingHeaderOnceWhenChainedPathFiltersProcessRequest() {
+		MockHttpServletRequest servletRequest = MockMvcRequestBuilders.get("http://localhost:8080/blue")
+			.remoteAddress("10.0.0.1:80")
+			.header(X_FORWARDED_PREFIX_HEADER, "/upstream")
+			.buildRequest(null);
+		ServerRequest request = ServerRequest.create(servletRequest, Collections.emptyList());
+
+		MvcUtils.addOriginalRequestUrl(request, URI.create("http://localhost:8080/tenant/api/blue"));
+		MvcUtils.addOriginalRequestUrl(request, URI.create("http://localhost:8080/api/blue"));
+
+		XForwardedRequestHeadersFilter filter = new XForwardedRequestHeadersFilter(
+				new XForwardedRequestHeadersFilterProperties(), ".*");
+
+		HttpHeaders headers = filter.apply(request.headers().asHttpHeaders(), request);
+
+		assertThat(headers.getFirst(X_FORWARDED_PREFIX_HEADER)).isEqualTo("/upstream,/tenant/api");
+	}
+
 }