diff --git a/src/libraries/System.Net.Sockets/tests/FunctionalTests/SendReceive/SendReceive.cs b/src/libraries/System.Net.Sockets/tests/FunctionalTests/SendReceive/SendReceive.cs
index b40047ff515d58..c320b753a8908b 100644
--- a/src/libraries/System.Net.Sockets/tests/FunctionalTests/SendReceive/SendReceive.cs
+++ b/src/libraries/System.Net.Sockets/tests/FunctionalTests/SendReceive/SendReceive.cs
@@ -1059,6 +1059,7 @@ await RetryHelper.ExecuteAsync(async () =>
                 (Socket socket1, Socket socket2) = SocketTestExtensions.CreateConnectedSocketPair(ipv6Server, dualModeClient);
                 using SafeSocketHandle? owner = ReplaceWithNonOwning(ref socket1, owning);
 
+                using (socket1)
                 using (socket2)
                 {
                     Task socketOperation;
@@ -1138,6 +1139,15 @@ await socketOperation
                                 peerSocketError = se.SocketErrorCode;
                                 break;
                             }
+                            catch (TimeoutException ex) when (!receiveOrSend && (PlatformDetection.IsApplePlatform || PlatformDetection.IsFreeBSD))
+                            {
+                                // BSD TCP stacks may reject a valid reset when sent data has not yet
+                                // been acknowledged. Retry with fresh sockets, not another receive.
+                                const string Message = "Timed out waiting for the peer to observe the connection reset, retry.";
+                                _output?.WriteLine(Message);
+                                _output?.WriteLine(ex.ToString());
+                                Assert.Fail(Message);
+                            }
                         }
 
                         try