diff --git a/src/libraries/System.Net.WebSockets/src/System/Net/WebSockets/ManagedWebSocket.cs b/src/libraries/System.Net.WebSockets/src/System/Net/WebSockets/ManagedWebSocket.cs
index 553a254c2770d4..9436a7f2731d59 100644
--- a/src/libraries/System.Net.WebSockets/src/System/Net/WebSockets/ManagedWebSocket.cs
+++ b/src/libraries/System.Net.WebSockets/src/System/Net/WebSockets/ManagedWebSocket.cs
@@ -510,15 +510,16 @@ private ValueTask SendFrameLockAcquiredNonCancelableAsync(MessageOpcode opcode,
                 if (writeTask.IsCompleted)
                 {
                     writeTask.GetAwaiter().GetResult();
-                    ValueTask flushTask = new ValueTask(_stream.FlushAsync());
+                    Task flushTask = _stream.FlushAsync();
                     if (flushTask.IsCompleted)
                     {
-                        return flushTask;
+                        flushTask.GetAwaiter().GetResult();
+                        return ValueTask.CompletedTask;
                     }
                     else
                     {
                         releaseSendBufferAndSemaphore = false;
-                        return WaitForWriteTaskAsync(flushTask, shouldFlush: false);
+                        return WaitForWriteTaskAsync(new ValueTask(flushTask), shouldFlush: false);
                     }
                 }
 
diff --git a/src/libraries/System.Net.WebSockets/tests/WebSocketTestStream.cs b/src/libraries/System.Net.WebSockets/tests/WebSocketTestStream.cs
index 64ec09f88807f2..e5a87210a43166 100644
--- a/src/libraries/System.Net.WebSockets/tests/WebSocketTestStream.cs
+++ b/src/libraries/System.Net.WebSockets/tests/WebSocketTestStream.cs
@@ -86,6 +86,12 @@ public Span<byte> NextAvailableBytes
         /// </summary>
         public bool IgnoreCancellationToken { get; set; }
 
+        /// <summary>
+        /// If set, causes FlushAsync to return a synchronously-faulted Task with this exception.
+        /// Used to exercise sync-completion-faulted code paths in the WebSocket send flow.
+        /// </summary>
+        public Exception? FlushException { get; set; }
+
         public override bool CanRead => true;
 
         public override bool CanSeek => false;
@@ -226,6 +232,15 @@ public override async ValueTask WriteAsync(ReadOnlyMemory<byte> buffer, Cancella
 
         public override void Flush() { }
 
+        public override Task FlushAsync(CancellationToken cancellationToken)
+        {
+            if (FlushException is not null)
+            {
+                return Task.FromException(FlushException);
+            }
+            return base.FlushAsync(cancellationToken);
+        }
+
         public override int Read(byte[] buffer, int offset, int count) => throw new NotSupportedException();
 
         public override long Seek(long offset, SeekOrigin origin) => throw new NotSupportedException();
diff --git a/src/libraries/System.Net.WebSockets/tests/WebSocketTests.cs b/src/libraries/System.Net.WebSockets/tests/WebSocketTests.cs
index 41c7fe341d266d..cf01437fc3d97d 100644
--- a/src/libraries/System.Net.WebSockets/tests/WebSocketTests.cs
+++ b/src/libraries/System.Net.WebSockets/tests/WebSocketTests.cs
@@ -182,6 +182,23 @@ public async Task ThrowWhenContinuationWithDifferentCompressionFlags()
                client.SendAsync(Memory<byte>.Empty, WebSocketMessageType.Binary, WebSocketMessageFlags.EndOfMessage, default));
         }
 
+        [Fact]
+        public async Task SendAsync_FlushAsyncSyncFaulted_WrapsExceptionInWebSocketException()
+        {
+            var underlying = new IOException("flush failed");
+            using var stream = new WebSocketTestStream { FlushException = underlying };
+            using WebSocket ws = WebSocket.CreateFromStream(
+                stream, isServer: false, subProtocol: null, keepAliveInterval: Timeout.InfiniteTimeSpan);
+
+            var buffer = new ArraySegment<byte>(new byte[] { 1, 2, 3 });
+
+            WebSocketException ex = await Assert.ThrowsAsync<WebSocketException>(
+                () => ws.SendAsync(buffer, WebSocketMessageType.Binary, endOfMessage: true, CancellationToken.None));
+
+            Assert.Equal(WebSocketError.ConnectionClosedPrematurely, ex.WebSocketErrorCode);
+            Assert.Same(underlying, ex.InnerException);
+        }
+
         [Fact]
         public async Task ReceiveAsync_ServerUnmaskedFrame_ThrowsWebSocketException()
         {