diff --git a/src/libraries/System.Net.WebSockets.Client/src/System/Net/WebSockets/ClientWebSocket.cs b/src/libraries/System.Net.WebSockets.Client/src/System/Net/WebSockets/ClientWebSocket.cs
index 487aab5594d813..4e55cd9575b8b4 100644
--- a/src/libraries/System.Net.WebSockets.Client/src/System/Net/WebSockets/ClientWebSocket.cs
+++ b/src/libraries/System.Net.WebSockets.Client/src/System/Net/WebSockets/ClientWebSocket.cs
@@ -135,6 +135,9 @@ public override Task SendAsync(ArraySegment<byte> buffer, WebSocketMessageType m
         public override ValueTask SendAsync(ReadOnlyMemory<byte> buffer, WebSocketMessageType messageType, bool endOfMessage, CancellationToken cancellationToken) =>
             ConnectedWebSocket.SendAsync(buffer, messageType, endOfMessage, cancellationToken);
 
+        public override ValueTask SendAsync(ReadOnlyMemory<byte> buffer, WebSocketMessageType messageType, WebSocketMessageFlags messageFlags, CancellationToken cancellationToken) =>
+            ConnectedWebSocket.SendAsync(buffer, messageType, messageFlags, cancellationToken);
+
         public override Task<WebSocketReceiveResult> ReceiveAsync(ArraySegment<byte> buffer, CancellationToken cancellationToken) =>
             ConnectedWebSocket.ReceiveAsync(buffer, cancellationToken);
 
diff --git a/src/libraries/System.Net.WebSockets.Client/tests/DeflateTests.cs b/src/libraries/System.Net.WebSockets.Client/tests/DeflateTests.cs
index 9836f31df16cb7..158aa0983a01b1 100644
--- a/src/libraries/System.Net.WebSockets.Client/tests/DeflateTests.cs
+++ b/src/libraries/System.Net.WebSockets.Client/tests/DeflateTests.cs
@@ -87,6 +87,91 @@ await LoopbackServer.CreateClientAndServerAsync(async uri =>
             }), new LoopbackServer.Options { WebSocketEndpoint = true });
         }
 
+        [ConditionalFact(nameof(WebSocketsSupported))]
+        public async Task ThrowsWhenContinuationHasDifferentCompressionFlags()
+        {
+            var deflateOpt = new WebSocketDeflateOptions
+            {
+                ClientMaxWindowBits = 14,
+                ClientContextTakeover = true,
+                ServerMaxWindowBits = 14,
+                ServerContextTakeover = true
+            };
+            await LoopbackServer.CreateClientAndServerAsync(async uri =>
+            {
+                using var cws = new ClientWebSocket();
+                using var cts = new CancellationTokenSource(TimeOutMilliseconds);
+
+                cws.Options.DangerousDeflateOptions = deflateOpt;
+                await ConnectAsync(cws, uri, cts.Token);
+
+
+                await cws.SendAsync(Memory<byte>.Empty, WebSocketMessageType.Text, WebSocketMessageFlags.DisableCompression, default);
+                Assert.Throws<ArgumentException>("messageFlags", () =>
+                   cws.SendAsync(Memory<byte>.Empty, WebSocketMessageType.Binary, WebSocketMessageFlags.EndOfMessage, default));
+            }, server => server.AcceptConnectionAsync(async connection =>
+            {
+                string extensionsReply = CreateDeflateOptionsHeader(deflateOpt);
+                await LoopbackHelper.WebSocketHandshakeAsync(connection, extensionsReply);
+            }), new LoopbackServer.Options { WebSocketEndpoint = true });
+        }
+
+        [ConditionalFact(nameof(WebSocketsSupported))]
+        public async Task SendHelloWithDisableCompression()
+        {
+            byte[] bytes = "Hello"u8.ToArray();
+
+            int prefixLength = 2;
+            byte[] rawPrefix = new byte[] { 0x81, 0x85 }; // fin=1, rsv=0, opcode=text; mask=1, len=5
+            int rawRemainingBytes = 9; // mask bytes (4) + payload bytes (5)
+            byte[] compressedPrefix = new byte[] { 0xc1, 0x87 }; // fin=1, rsv=compressed, opcode=text; mask=1, len=7
+            int compressedRemainingBytes = 11; // mask bytes (4) + payload bytes (7)
+
+            var deflateOpt = new WebSocketDeflateOptions
+            {
+                ClientMaxWindowBits = 14,
+                ClientContextTakeover = true,
+                ServerMaxWindowBits = 14,
+                ServerContextTakeover = true
+            };
+
+            await LoopbackServer.CreateClientAndServerAsync(async uri =>
+            {
+                using var cws = new ClientWebSocket();
+                using var cts = new CancellationTokenSource(TimeOutMilliseconds);
+
+                cws.Options.DangerousDeflateOptions = deflateOpt;
+                await ConnectAsync(cws, uri, cts.Token);
+
+                await cws.SendAsync(bytes, WebSocketMessageType.Text, true, cts.Token);
+
+                WebSocketMessageFlags flags = WebSocketMessageFlags.DisableCompression | WebSocketMessageFlags.EndOfMessage;
+                await cws.SendAsync(bytes, WebSocketMessageType.Text, flags, cts.Token);
+            }, server => server.AcceptConnectionAsync(async connection =>
+            {
+                var buffer = new byte[compressedRemainingBytes];
+                string extensionsReply = CreateDeflateOptionsHeader(deflateOpt);
+                await LoopbackHelper.WebSocketHandshakeAsync(connection, extensionsReply);
+
+                // first message is compressed
+                await ReadExactAsync(buffer, prefixLength);
+                Assert.Equal(compressedPrefix, buffer[..prefixLength]);
+                // read rest of the frame
+                await ReadExactAsync(buffer, compressedRemainingBytes);
+
+                // second message is not compressed
+                await ReadExactAsync(buffer, prefixLength);
+                Assert.Equal(rawPrefix, buffer[..prefixLength]);
+                // read rest of the frame
+                await ReadExactAsync(buffer, rawRemainingBytes);
+
+                async Task ReadExactAsync(byte[] buf, int n)
+                {
+                    await connection.Stream.ReadAtLeastAsync(buf.AsMemory(0, n), n);
+                }
+            }), new LoopbackServer.Options { WebSocketEndpoint = true });
+        }
+
         private static string CreateDeflateOptionsHeader(WebSocketDeflateOptions options)
         {
             var builder = new StringBuilder();