diff --git a/x/configurl/module.go b/x/configurl/module.go
index 83e14b89..3e11f10c 100644
--- a/x/configurl/module.go
+++ b/x/configurl/module.go
@@ -65,6 +65,8 @@ func RegisterDefaultProviders(c *ProviderContainer) *ProviderContainer {
 	registerWebsocketStreamDialer(&c.StreamDialers, "ws", c.StreamDialers.NewInstance)
 	registerWebsocketPacketDialer(&c.PacketDialers, "ws", c.StreamDialers.NewInstance)
 
+	registerWaitStreamDialer(&c.StreamDialers, "waitstream", c.StreamDialers.NewInstance)
+
 	return c
 }
 
diff --git a/x/configurl/wait_stream.go b/x/configurl/wait_stream.go
new file mode 100644
index 00000000..f6e1f4bf
--- /dev/null
+++ b/x/configurl/wait_stream.go
@@ -0,0 +1,62 @@
+// Copyright 2024 The Outline Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     https://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package configurl
+
+import (
+	"context"
+	"fmt"
+	"net/url"
+	"time"
+
+	"github.com/Jigsaw-Code/outline-sdk/transport"
+	"github.com/Jigsaw-Code/outline-sdk/x/wait_stream"
+)
+
+func registerWaitStreamDialer(r TypeRegistry[transport.StreamDialer], typeID string, newSD BuildFunc[transport.StreamDialer]) {
+	r.RegisterType(typeID, func(ctx context.Context, config *Config) (transport.StreamDialer, error) {
+		sd, err := newSD(ctx, config.BaseConfig)
+		if err != nil {
+			return nil, err
+		}
+
+		queryUrlParameters, err := url.ParseQuery(config.URL.Opaque)
+		if err != nil {
+			return nil, fmt.Errorf("waitstream: failed to parse URL parameters: %w", err)
+		}
+
+		resultStreamDialer, err := wait_stream.NewStreamDialer(sd)
+		if err != nil {
+			return nil, err
+		}
+
+		if queryUrlParameters.Has("timeout") {
+			timeout, err := time.ParseDuration(queryUrlParameters.Get("timeout"))
+			if err != nil {
+				return nil, fmt.Errorf("waitstream: failed to parse timeout parameter: %w", err)
+			}
+			resultStreamDialer.SetWaitingTimeout(timeout)
+		}
+
+		if queryUrlParameters.Has("delay") {
+			delay, err := time.ParseDuration(queryUrlParameters.Get("delay"))
+			if err != nil {
+				return nil, fmt.Errorf("waitstream: failed to parse delay parameter: %w", err)
+			}
+			resultStreamDialer.SetWaitingDelay(delay)
+		}
+
+		return resultStreamDialer, err
+	})
+}
diff --git a/x/wait_stream/is_sending_bytes_linux.go b/x/wait_stream/is_sending_bytes_linux.go
new file mode 100644
index 00000000..751a7045
--- /dev/null
+++ b/x/wait_stream/is_sending_bytes_linux.go
@@ -0,0 +1,15 @@
+//go:build linux
+
+package wait_stream
+
+import (
+	"golang.org/x/sys/unix"
+)
+
+func isSocketFdSendingBytes(fd int) (bool, error) {
+	tcpInfo, err := unix.GetsockoptTCPInfo(fd, unix.IPPROTO_TCP, unix.TCP_INFO)
+	if err != nil {
+		return false, err
+	}
+	return tcpInfo.Notsent_bytes != 0, nil
+}
diff --git a/x/wait_stream/is_sending_bytes_not_implemented.go b/x/wait_stream/is_sending_bytes_not_implemented.go
new file mode 100644
index 00000000..2c89203a
--- /dev/null
+++ b/x/wait_stream/is_sending_bytes_not_implemented.go
@@ -0,0 +1,12 @@
+//go:build !linux
+
+package wait_stream
+
+import (
+	"errors"
+	"fmt"
+)
+
+func isSocketFdSendingBytes(_ int) (bool, error) {
+	return false, fmt.Errorf("%w: checking if socket is sending bytes is not implemented on this platform", errors.ErrUnsupported)
+}
diff --git a/x/wait_stream/stream_dialer.go b/x/wait_stream/stream_dialer.go
new file mode 100644
index 00000000..4a1f8bc1
--- /dev/null
+++ b/x/wait_stream/stream_dialer.go
@@ -0,0 +1,76 @@
+// Copyright 2024 The Outline Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     https://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package wait_stream
+
+import (
+	"context"
+	"errors"
+	"net"
+	"time"
+
+	"github.com/Jigsaw-Code/outline-sdk/transport"
+)
+
+type WaitStreamDialer struct {
+	dialer transport.StreamDialer
+
+	// Stop waiting on a packet after this timeout
+	waitingTimeout time.Duration
+	// Check if socket is sending bytes that often
+	waitingDelay time.Duration
+}
+
+var _ transport.StreamDialer = (*WaitStreamDialer)(nil)
+
+// byeDPI uses a default delay of 500ms with 1ms sleep
+// We might reconsider the defaults later, if needed.
+// https://github.com/hufrea/byedpi/blob/main/desync.c#L90
+var defaultTimeout = time.Millisecond * 10
+var defaultDelay = time.Microsecond * 1
+
+func NewStreamDialer(dialer transport.StreamDialer) (*WaitStreamDialer, error) {
+	if dialer == nil {
+		return nil, errors.New("argument dialer must not be nil")
+	}
+	return &WaitStreamDialer{
+		dialer:         dialer,
+		waitingTimeout: defaultTimeout,
+		waitingDelay:   defaultDelay,
+	}, nil
+}
+
+func (d *WaitStreamDialer) SetWaitingTimeout(timeout time.Duration) {
+	d.waitingTimeout = timeout
+}
+
+func (d *WaitStreamDialer) SetWaitingDelay(timeout time.Duration) {
+	d.waitingDelay = timeout
+}
+
+func (d *WaitStreamDialer) DialStream(ctx context.Context, remoteAddr string) (transport.StreamConn, error) {
+	innerConn, err := d.dialer.DialStream(ctx, remoteAddr)
+	if err != nil {
+		return nil, err
+	}
+
+	tcpInnerConn, ok := innerConn.(*net.TCPConn)
+	if !ok {
+		return nil, errors.New("wait_stream strategy: expected base dialer to return TCPConn")
+	}
+
+	dw := NewWriter(tcpInnerConn, d.waitingTimeout, d.waitingDelay)
+
+	return transport.WrapConn(innerConn, innerConn, dw), nil
+}
diff --git a/x/wait_stream/writer.go b/x/wait_stream/writer.go
new file mode 100644
index 00000000..ab59e361
--- /dev/null
+++ b/x/wait_stream/writer.go
@@ -0,0 +1,79 @@
+// Copyright 2024 The Outline Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     https://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package wait_stream
+
+import (
+	"errors"
+	"fmt"
+	"io"
+	"net"
+	"time"
+)
+
+type waitStreamWriter struct {
+	conn *net.TCPConn
+
+	waitingTimeout time.Duration
+	waitingDelay   time.Duration
+}
+
+var _ io.Writer = (*waitStreamWriter)(nil)
+
+func NewWriter(conn *net.TCPConn, waitingTimeout time.Duration, waitingDelay time.Duration) io.Writer {
+	return &waitStreamWriter{
+		conn:           conn,
+		waitingTimeout: waitingTimeout,
+		waitingDelay:   waitingDelay,
+	}
+}
+
+func isConnectionSendingBytes(conn *net.TCPConn) (result bool, err error) {
+	syscallConn, err := conn.SyscallConn()
+	if err != nil {
+		return false, err
+	}
+	syscallConn.Control(func(fd uintptr) {
+		result, err = isSocketFdSendingBytes(int(fd))
+	})
+	return
+}
+
+func waitUntilBytesAreSent(conn *net.TCPConn, waitingTimeout time.Duration, waitingDelay time.Duration) error {
+	startTime := time.Now()
+	for time.Since(startTime) < waitingTimeout {
+		isSendingBytes, err := isConnectionSendingBytes(conn)
+		if err != nil {
+			return err
+		}
+		if !isSendingBytes {
+			return nil
+		}
+
+		time.Sleep(waitingDelay)
+	}
+	// not sure about the right behaviour here: fail or give up waiting?
+	// giving up feels safer, and matches byeDPI behavior
+	return nil
+}
+
+func (w *waitStreamWriter) Write(data []byte) (written int, err error) {
+	// This may not be implemented, so it's best effort really.
+	waitUntilBytesAreSentErr := waitUntilBytesAreSent(w.conn, w.waitingTimeout, w.waitingDelay)
+	if waitUntilBytesAreSentErr != nil && !errors.Is(waitUntilBytesAreSentErr, errors.ErrUnsupported) {
+		return 0, fmt.Errorf("error when waiting for stream to send all bytes: %w", waitUntilBytesAreSentErr)
+	}
+
+	return w.conn.Write(data)
+}