diff --git a/spring-web/src/main/java/org/springframework/web/server/adapter/HttpWebHandlerAdapter.java b/spring-web/src/main/java/org/springframework/web/server/adapter/HttpWebHandlerAdapter.java
index c34f872243a..125a38816ed 100644
--- a/spring-web/src/main/java/org/springframework/web/server/adapter/HttpWebHandlerAdapter.java
+++ b/spring-web/src/main/java/org/springframework/web/server/adapter/HttpWebHandlerAdapter.java
@@ -362,15 +362,14 @@ public class HttpWebHandlerAdapter extends WebHandlerDecorator implements HttpHa
 		ServerHttpResponse response = exchange.getResponse();
 		String logPrefix = exchange.getLogPrefix();
 
-		// Sometimes a remote call error can look like a disconnected client.
-		// Try to set the response first before the "isDisconnectedClient" check.
-
-		if (response.setStatusCode(HttpStatus.INTERNAL_SERVER_ERROR)) {
-			logger.error(logPrefix + "500 Server Error for " + formatRequest(request), ex);
+		if (disconnectedClientHelper.checkAndLogClientDisconnectedException(ex)) {
+			// Attempt to send 500 in case of onward (rather than client) connection issue
+			response.setStatusCode(HttpStatus.INTERNAL_SERVER_ERROR);
+			observationContext.setConnectionAborted(true);
 			return Mono.empty();
 		}
-		else if (disconnectedClientHelper.checkAndLogClientDisconnectedException(ex)) {
-			observationContext.setConnectionAborted(true);
+		else if (response.setStatusCode(HttpStatus.INTERNAL_SERVER_ERROR)) {
+			logger.error(logPrefix + "500 Server Error for " + formatRequest(request), ex);
 			return Mono.empty();
 		}
 		else {