diff --git a/initiatorpool/errors.go b/initiatorpool/errors.go
index 2044cce..8dfb8b4 100644
--- a/initiatorpool/errors.go
+++ b/initiatorpool/errors.go
@@ -4,18 +4,27 @@ import "errors"
 import "fmt"
 
 var (
+	// Config errors
 	InvalidKeepaliveTimeout = errors.New("keepalive timeout cannot be negative")
 	InvalidMaxQueueSize     = errors.New("maximum queue size cannot be negative")
+
+	// Pool errors
+	ErrPoolClosed   = errors.New("pool is closed")
+	ErrPeerNotFound = errors.New("peer not found")
+	ErrPeerExists   = errors.New("peer already exists")
+
+	// Worker errors
+	ErrConnectionUnavailable = errors.New("connection unavailable")
 )
 
 func NewConfigError(text string) error {
 	return fmt.Errorf("configuration error: %s", text)
 }
 
-func NewPoolError(text string) error {
-	return fmt.Errorf("pool error: %s", text)
+func NewPoolError(err error) error {
+	return fmt.Errorf("pool error: %w", err)
 }
 
-func NewWorkerError(id string, text string) error {
-	return fmt.Errorf("worker %q error: %s", id, text)
+func NewWorkerError(id string, err error) error {
+	return fmt.Errorf("worker %q error: %w", id, err)
 }
diff --git a/initiatorpool/helper_test.go b/initiatorpool/helper_test.go
new file mode 100644
index 0000000..a275bae
--- /dev/null
+++ b/initiatorpool/helper_test.go
@@ -0,0 +1,62 @@
+package initiatorpool
+
+import (
+	"fmt"
+	"git.wisehodl.dev/jay/go-honeybee/honeybeetest"
+	"git.wisehodl.dev/jay/go-honeybee/transport"
+	"github.com/stretchr/testify/assert"
+	"io"
+	"testing"
+)
+
+func setupWorkerTestConnection(t *testing.T) (
+	conn *transport.Connection,
+	mockSocket *honeybeetest.MockSocket,
+	incomingData chan honeybeetest.MockIncomingData,
+	outgoingData chan honeybeetest.MockOutgoingData,
+) {
+	t.Helper()
+
+	incomingData = make(chan honeybeetest.MockIncomingData, 100)
+	outgoingData = make(chan honeybeetest.MockOutgoingData, 100)
+	mockSocket = honeybeetest.NewMockSocket()
+
+	mockSocket.CloseFunc = func() error {
+		mockSocket.Once.Do(func() { close(mockSocket.Closed) })
+		return nil
+	}
+
+	mockSocket.ReadMessageFunc = func() (int, []byte, error) {
+		select {
+		case data := <-incomingData:
+			return data.MsgType, data.Data, data.Err
+		case <-mockSocket.Closed:
+			return 0, nil, io.EOF
+		}
+	}
+
+	mockSocket.WriteMessageFunc = func(msgType int, data []byte) error {
+		select {
+		case outgoingData <- honeybeetest.MockOutgoingData{MsgType: msgType, Data: data}:
+			return nil
+		case <-mockSocket.Closed:
+			return io.EOF
+		default:
+			return fmt.Errorf("mock outgoing channel unavailable")
+		}
+	}
+
+	var err error
+	conn, err = transport.NewConnectionFromSocket(mockSocket, nil, nil)
+	assert.NoError(t, err)
+	return
+}
+
+func connClosed(conn *transport.Connection) bool {
+	select {
+	case _, ok := <-conn.Errors():
+		return !ok
+	default:
+		return false
+	}
+}
diff --git a/initiatorpool/pool.go b/initiatorpool/pool.go
index faecbc6..ed85c78 100644
--- a/initiatorpool/pool.go
+++ b/initiatorpool/pool.go
@@ -155,12 +155,12 @@ func (p *Pool) Connect(id string) error {
 	defer p.mu.Unlock()
 
 	if p.closed {
-		return NewPoolError("pool is closed")
+		return NewPoolError(ErrPoolClosed)
 	}
 	_, exists := p.peers[id]
 
 	if exists {
-		return NewPoolError("connection already exists")
+		return NewPoolError(ErrPeerExists)
 	}
 
 	// The worker factory must be non-blocking to avoid deadlocks
@@ -199,13 +199,13 @@ func (p *Pool) Remove(id string) error {
 	p.mu.Lock()
 	if p.closed {
 		p.mu.Unlock()
-		return NewPoolError("pool is closed")
+		return NewPoolError(ErrPoolClosed)
 	}
 
 	peer, exists := p.peers[id]
 	if !exists {
 		p.mu.Unlock()
-		return NewPoolError("connection not found")
+		return NewPoolError(ErrPeerNotFound)
 	}
 	delete(p.peers, id)
 	p.mu.Unlock()
@@ -225,12 +225,12 @@ func (p *Pool) Send(id string, data []byte) error {
 	defer p.mu.RUnlock()
 
 	if p.closed {
-		return NewPoolError("pool is closed")
+		return NewPoolError(ErrPoolClosed)
 	}
 
 	peer, exists := p.peers[id]
 	if !exists {
-		return NewPoolError("connection not found")
+		return NewPoolError(ErrPeerNotFound)
 	}
 
 	return peer.worker.Send(data)
diff --git a/initiatorpool/pool_test.go b/initiatorpool/pool_test.go
index ccc62fa..b887a0b 100644
--- a/initiatorpool/pool_test.go
+++ b/initiatorpool/pool_test.go
@@ -64,7 +64,7 @@ func _TestPoolConnect(t *testing.T) {
 		// trailing slash normalizes to same key
 		err = pool.Connect("wss://test/")
 		assert.Error(t, err)
-		assert.ErrorContains(t, err, "already exists")
+		assert.ErrorIs(t, err, ErrPeerExists)
 
 		pool.mu.RLock()
 		assert.Len(t, pool.peers, 1)
@@ -152,7 +152,7 @@ func _TestPoolRemove(t *testing.T) {
 
 		// remove unknown connection
 		err = pool.Remove("wss://unknown")
-		assert.ErrorContains(t, err, "connection not found")
+		assert.ErrorIs(t, err, ErrPeerNotFound)
 	})
 
 	t.Run("closed pool returns error", func(t *testing.T) {
@@ -172,7 +172,7 @@ func _TestPoolRemove(t *testing.T) {
 
 		// attempt to remove connection
 		err = pool.Remove("wss://test")
-		assert.ErrorContains(t, err, "pool is closed")
+		assert.ErrorIs(t, err, ErrPoolClosed)
 	})
 
 }
diff --git a/initiatorpool/worker.go b/initiatorpool/worker.go
index ed495df..fb58e08 100644
--- a/initiatorpool/worker.go
+++ b/initiatorpool/worker.go
@@ -5,6 +5,7 @@ import (
 	"context"
 	"git.wisehodl.dev/jay/go-honeybee/transport"
 	"sync"
+	"sync/atomic"
 	"time"
 )
 
@@ -16,11 +17,14 @@ type receivedMessage struct {
 }
 
 type Worker struct {
-	ctx      context.Context
-	cancel   context.CancelFunc
-	id       string
-	config   *WorkerConfig
-	outbound chan []byte
+	ctx    context.Context
+	cancel context.CancelFunc
+
+	id     string
+	config *WorkerConfig
+
+	conn      atomic.Pointer[transport.Connection]
+	heartbeat chan struct{}
 }
 
 func NewWorker(
@@ -40,25 +44,34 @@ func NewWorker(
 
 	wctx, cancel := context.WithCancel(ctx)
 	w := &Worker{
-		ctx:      wctx,
-		cancel:   cancel,
-		id:       id,
-		outbound: make(chan []byte, 64),
-		config:   config,
+		ctx:       wctx,
+		cancel:    cancel,
+		id:        id,
+		config:    config,
+		heartbeat: make(chan struct{}),
 	}
 
 	return w, nil
 }
 
 func (w *Worker) Send(data []byte) error {
-	select {
-	case w.outbound <- data:
-		return nil
-	case <-w.ctx.Done():
-		return NewWorkerError(w.id, "worker is stopped")
-	default:
-		return NewWorkerError(w.id, "outbound queue full")
+	conn := w.conn.Load()
+	if conn == nil {
+		return NewWorkerError(w.id, ErrConnectionUnavailable)
 	}
+
+	err := conn.Send(data)
+
+	if err != nil {
+		return NewWorkerError(w.id, err)
+	}
+
+	select {
+	case w.heartbeat <- struct{}{}:
+	case <-w.ctx.Done():
+	}
+
+	return nil
 }
 
 func (w *Worker) Start(
@@ -76,7 +89,6 @@ func (w *Worker) runSession(
 	wctx WorkerContext,
 
 	messages chan<- receivedMessage,
-	heartbeat chan<- struct{},
 	dial chan<- struct{},
 
 	keepalive <-chan struct{},
@@ -88,19 +100,38 @@ func (w *Worker) runSession(
 func (w *Worker) runReader(
 	conn *transport.Connection,
 	messages chan<- receivedMessage,
-	heartbeat chan<- struct{},
 	sessionDone <-chan struct{},
 	onStop func(),
 ) {
-}
+	defer func() {
+		conn.Close()
+		onStop()
+	}()
 
-func (w *Worker) runWriter(
-	conn *transport.Connection,
-	outbound <-chan []byte,
-	heartbeat chan<- struct{},
-	sessionDone <-chan struct{},
-	onStop func(),
-) {
+	for {
+		select {
+		case <-sessionDone:
+			return
+		case data, ok := <-conn.Incoming():
+			if !ok {
+				// connection has closed
+				return
+			}
+
+			// send message forward
+			messages <- receivedMessage{
+				data:       data,
+				receivedAt: time.Now(),
+			}
+
+			// send heartbeat
+			select {
+			case w.heartbeat <- struct{}{}:
+			case <-sessionDone:
+				return
+			}
+		}
+	}
 }
 
 func (w *Worker) runStopMonitor(
@@ -110,6 +141,16 @@ func (w *Worker) runStopMonitor(
 	sessionDone <-chan struct{},
 	onStop func(),
 ) {
+	defer func() {
+		conn.Close()
+		onStop()
+	}()
+
+	select {
+	case <-ctx.Done():
+	case <-keepalive:
+	case <-sessionDone:
+	}
 }
 
 func (w *Worker) runForwarder(
@@ -157,7 +198,6 @@ func (w *Worker) runForwarder(
 
 func (w *Worker) runKeepalive(
 	ctx context.Context,
-	heartbeat <-chan struct{},
 	keepalive chan<- struct{},
 ) {
 	// disable keepalive timeout if not configured
@@ -176,7 +216,7 @@ func (w *Worker) runKeepalive(
 		select {
 		case <-ctx.Done():
 			return
-		case <-heartbeat:
+		case <-w.heartbeat:
 			// drain the timer channel and reset
 			if !timer.Stop() {
 				select {
diff --git a/initiatorpool/worker_test.go b/initiatorpool/worker_test.go
index 8e31119..829a734 100644
--- a/initiatorpool/worker_test.go
+++ b/initiatorpool/worker_test.go
@@ -8,6 +8,7 @@ import (
 	"git.wisehodl.dev/jay/go-honeybee/types"
 	"github.com/stretchr/testify/assert"
 	"net/http"
+	"sync"
 	"sync/atomic"
 	"testing"
 	"time"
@@ -109,18 +110,21 @@ func TestRunForwarder(t *testing.T) {
 
 func TestRunKeepalive(t *testing.T) {
 	t.Run("heartbeat resets timer, no keepalive signal fired", func(t *testing.T) {
-		heartbeat := make(chan struct{}, 3)
+		heartbeat := make(chan struct{})
 		keepalive := make(chan struct{}, 1)
 		ctx, cancel := context.WithCancel(context.Background())
 		defer cancel()
 
-		w := &Worker{config: &WorkerConfig{KeepaliveTimeout: 100 * time.Millisecond}}
-		go w.runKeepalive(ctx, heartbeat, keepalive)
+		w := &Worker{
+			config:    &WorkerConfig{KeepaliveTimeout: 100 * time.Millisecond},
+			heartbeat: heartbeat,
+		}
+		go w.runKeepalive(ctx, keepalive)
 
 		// send heartbeats faster than the timeout
 		for i := 0; i < 5; i++ {
 			time.Sleep(30 * time.Millisecond)
-			heartbeat <- struct{}{}
+			w.heartbeat <- struct{}{}
 		}
 
 		// because the timer is being reset, keepalive signal should not be sent
@@ -135,13 +139,12 @@ func TestRunKeepalive(t *testing.T) {
 	})
 
 	t.Run("keepalive timeout fires signal", func(t *testing.T) {
-		heartbeat := make(chan struct{})
 		keepalive := make(chan struct{}, 1)
 		ctx, cancel := context.WithCancel(context.Background())
 		defer cancel()
 
 		w := &Worker{config: &WorkerConfig{KeepaliveTimeout: 20 * time.Millisecond}}
-		go w.runKeepalive(ctx, heartbeat, keepalive)
+		go w.runKeepalive(ctx, keepalive)
 
 		// send no heartbeats, wait for timeout and keepalive signal
 		assert.Eventually(t, func() bool {
@@ -155,14 +158,13 @@ func TestRunKeepalive(t *testing.T) {
 	})
 
 	t.Run("exits on context cancellation", func(t *testing.T) {
-		heartbeat := make(chan struct{})
 		keepalive := make(chan struct{}, 1)
 		ctx, cancel := context.WithCancel(context.Background())
 
 		w := &Worker{config: &WorkerConfig{KeepaliveTimeout: 20 * time.Second}}
 		done := make(chan struct{})
 		go func() {
-			w.runKeepalive(ctx, heartbeat, keepalive)
+			w.runKeepalive(ctx, keepalive)
 			close(done)
 		}()
 
@@ -178,6 +180,73 @@ func TestRunKeepalive(t *testing.T) {
 	})
 }
 
+func TestRunStopMonitor(t *testing.T) {
+	t.Run("keepalive signal calls conn.Close and onStop", func(t *testing.T) {
+		conn, _, _, _ := setupWorkerTestConnection(t)
+		ctx, cancel := context.WithCancel(context.Background())
+		defer cancel()
+
+		keepalive := make(chan struct{}, 1)
+		sessionDone := make(chan struct{})
+		onStopCalled := atomic.Bool{}
+		onStop := func() { onStopCalled.Store(true) }
+
+		w := &Worker{id: "wss://test"}
+		go w.runStopMonitor(ctx, conn, keepalive, sessionDone, onStop)
+
+		keepalive <- struct{}{}
+
+		assert.Eventually(t, func() bool {
+			return connClosed(conn)
+		}, honeybeetest.TestTimeout, honeybeetest.TestTick)
+
+		assert.True(t, onStopCalled.Load())
+	})
+
+	t.Run("ctx.Done calls conn.Close and onStop", func(t *testing.T) {
+		conn, _, _, _ := setupWorkerTestConnection(t)
+		ctx, cancel := context.WithCancel(context.Background())
+
+		keepalive := make(chan struct{})
+		sessionDone := make(chan struct{})
+		onStopCalled := atomic.Bool{}
+		onStop := func() { onStopCalled.Store(true) }
+
+		w := &Worker{id: "wss://test"}
+		go w.runStopMonitor(ctx, conn, keepalive, sessionDone, onStop)
+
+		cancel()
+
+		assert.Eventually(t, func() bool {
+			return connClosed(conn)
+		}, honeybeetest.TestTimeout, honeybeetest.TestTick)
+
+		assert.True(t, onStopCalled.Load())
+	})
+
+	t.Run("sessionDone close calls conn.Close and onStop", func(t *testing.T) {
+		conn, _, _, _ := setupWorkerTestConnection(t)
+		ctx, cancel := context.WithCancel(context.Background())
+		defer cancel()
+
+		keepalive := make(chan struct{})
+		sessionDone := make(chan struct{})
+		onStopCalled := atomic.Bool{}
+		onStop := func() { onStopCalled.Store(true) }
+
+		w := &Worker{id: "wss://test"}
+		go w.runStopMonitor(ctx, conn, keepalive, sessionDone, onStop)
+
+		close(sessionDone)
+
+		assert.Eventually(t, func() bool {
+			return connClosed(conn)
+		}, honeybeetest.TestTimeout, honeybeetest.TestTick)
+
+		assert.True(t, onStopCalled.Load())
+	})
+}
+
 func TestRunDialer(t *testing.T) {
 	t.Run("successful dial delivers connection to newConn", func(t *testing.T) {
 		w := &Worker{id: "wss://test"}
@@ -395,3 +464,104 @@ func TestRunDialer(t *testing.T) {
 		assert.Empty(t, newConn)
 	})
 }
+
+func TestWorkerSend(t *testing.T) {
+	t.Run("data sent to mock socket", func(t *testing.T) {
+		conn, _, _, outgoingData := setupWorkerTestConnection(t)
+		defer conn.Close()
+
+		ctx, cancel := context.WithCancel(context.Background())
+
+		heartbeat := make(chan struct{})
+		heartbeatCount := atomic.Int32{}
+
+		w := &Worker{
+			ctx:       ctx,
+			cancel:    cancel,
+			id:        "wss://test",
+			heartbeat: heartbeat,
+		}
+		w.conn.Store(conn)
+		defer w.cancel()
+
+		go func() {
+			for range heartbeat {
+				heartbeatCount.Add(1)
+			}
+		}()
+
+		testData := []byte("hello")
+		err := w.Send(testData)
+		assert.NoError(t, err)
+
+		// one heartbeat was sent
+		assert.Equal(t, 1, int(heartbeatCount.Load()))
+
+		// message was sent by the socket
+		assert.Eventually(t, func() bool {
+			select {
+			case msg := <-outgoingData:
+				return string(msg.Data) == "hello"
+			default:
+				return false
+			}
+		}, honeybeetest.TestTimeout, honeybeetest.TestTick)
+	})
+
+	t.Run("sends one heartbeat per successful send", func(t *testing.T) {
+		conn, _, _, _ := setupWorkerTestConnection(t)
+		defer conn.Close()
+
+		ctx, cancel := context.WithCancel(context.Background())
+
+		heartbeat := make(chan struct{})
+		heartbeatCount := atomic.Int32{}
+
+		w := &Worker{
+			ctx:       ctx,
+			cancel:    cancel,
+			id:        "wss://test",
+			heartbeat: heartbeat,
+		}
+		w.conn.Store(conn)
+		defer w.cancel()
+
+		go func() {
+			for range heartbeat {
+				heartbeatCount.Add(1)
+			}
+		}()
+
+		const count = 3
+		for i := 0; i < count; i++ {
+			err := w.Send([]byte(fmt.Sprintf("msg-%d", i)))
+			assert.NoError(t, err)
+		}
+
+		assert.Equal(t, count, int(heartbeatCount.Load()))
+	})
+
+	t.Run("returns error if connection is unavailable", func(t *testing.T) {
+		// no connection available to worker
+
+		ctx, cancel := context.WithCancel(context.Background())
+
+		heartbeat := make(chan struct{})
+
+		w := &Worker{
+			ctx:       ctx,
+			cancel:    cancel,
+			id:        "wss://test",
+			heartbeat: heartbeat,
+		}
+		defer w.cancel()
+
+		go func() {
+			for range heartbeat {
+			}
+		}()
+
+		err := w.Send([]byte("hello"))
+		assert.ErrorIs(t, err, ErrConnectionUnavailable)
+	})
+}
diff --git a/transport/connection.go b/transport/connection.go
index 4867ad2..4ede803 100644
--- a/transport/connection.go
+++ b/transport/connection.go
@@ -45,15 +45,15 @@ type Connection struct {
 	logger *slog.Logger
 
 	incoming chan []byte
-	outgoing chan []byte
 	errors   chan error
 	done     chan struct{}
 
 	state ConnectionState
 
-	wg     sync.WaitGroup
-	closed bool
-	mu     sync.RWMutex
+	wg      sync.WaitGroup
+	closed  bool
+	mu      sync.RWMutex
+	writeMu sync.Mutex
 }
 
 func NewConnection(urlStr string, config *ConnectionConfig, logger *slog.Logger) (*Connection, error) {
@@ -77,7 +77,6 @@ func NewConnection(urlStr string, config *ConnectionConfig, logger *slog.Logger)
 		config:   config,
 		logger:   logger,
 		incoming: make(chan []byte, 100),
-		outgoing: make(chan []byte, 100),
 		errors:   make(chan error, 10),
 		state:    StateDisconnected,
 		done:     make(chan struct{}),
@@ -108,7 +107,6 @@ func NewConnectionFromSocket(
 		config:   config,
 		logger:   logger,
 		incoming: make(chan []byte, 100),
-		outgoing: make(chan []byte, 100),
 		errors:   make(chan error, 10),
 		state:    StateConnected,
 		done:     make(chan struct{}),
@@ -119,7 +117,6 @@ func NewConnectionFromSocket(
 	}
 
 	conn.startReader()
-	conn.startWriter()
 
 	return conn, nil
 }
@@ -166,7 +163,6 @@ func (c *Connection) Connect(ctx context.Context) error {
 	}
 
 	c.startReader()
-	c.startWriter()
 
 	return nil
 }
@@ -221,63 +217,32 @@ func (c *Connection) startReader() {
 
 }
 
-func (c *Connection) startWriter() {
-	c.wg.Add(1)
-	go func() {
-		defer c.wg.Done()
-
-		for {
-			select {
-			case <-c.done:
-				return
-			case data := <-c.outgoing:
-				if c.config.WriteTimeout > 0 {
-					if err := c.socket.SetWriteDeadline(time.Now().Add(c.config.WriteTimeout)); err != nil {
-						if c.logger != nil {
-							c.logger.Error("write deadline error", "error", err)
-						}
-						select {
-						case c.errors <- fmt.Errorf("failed to set write deadline: %w", err):
-						case <-c.done:
-						}
-						c.shutdown()
-						return
-					}
-				}
-
-				if err := c.socket.WriteMessage(websocket.TextMessage, data); err != nil {
-					if c.logger != nil {
-						c.logger.Error("write error", "error", err)
-					}
-					select {
-					case c.errors <- err:
-					case <-c.done:
-					}
-					c.shutdown()
-					return
-				}
-			}
-		}
-	}()
-
-}
-
 func (c *Connection) Send(data []byte) error {
-	c.mu.RLock()
-	defer c.mu.RUnlock()
+	c.writeMu.Lock()
+	defer c.writeMu.Unlock()
 
 	if c.closed {
-		return NewConnectionError("connection closed")
+		return ErrConnectionClosed
 	}
 
-	select {
-	case c.outgoing <- data:
-		return nil
-	case <-c.done:
-		return NewConnectionError("connection closing")
-	default:
-		return NewConnectionError("outgoing queue full")
+	if c.config.WriteTimeout > 0 {
+		if err := c.socket.SetWriteDeadline(time.Now().Add(c.config.WriteTimeout)); err != nil {
+			if c.logger != nil {
+				c.logger.Error("write deadline error", "error", err)
+			}
+			c.shutdown()
+			return fmt.Errorf("failed to set write deadline: %w", err)
+		}
 	}
+
+	if err := c.socket.WriteMessage(websocket.TextMessage, data); err != nil {
+		if c.logger != nil {
+			c.logger.Error("write error", "error", err)
+		}
+		return fmt.Errorf("%w: %w", ErrWriteFailed, err)
+	}
+
+	return nil
 }
 
 func (c *Connection) Incoming() <-chan []byte {
@@ -326,7 +291,6 @@ func (c *Connection) shutdown() {
 
 		c.wg.Wait()
 		close(c.incoming)
-		close(c.outgoing)
 		close(c.errors)
 	}()
 
diff --git a/transport/connection_goroutine_test.go b/transport/connection_goroutine_test.go
index df54e0c..8203c63 100644
--- a/transport/connection_goroutine_test.go
+++ b/transport/connection_goroutine_test.go
@@ -5,10 +5,7 @@ import (
 	"git.wisehodl.dev/jay/go-honeybee/honeybeetest"
 	"github.com/gorilla/websocket"
 	"github.com/stretchr/testify/assert"
-	"io"
-	"strings"
 	"testing"
-	"time"
 )
 
 func TestStartReader(t *testing.T) {
@@ -88,198 +85,3 @@ func TestStartReader(t *testing.T) {
 		}, honeybeetest.TestTimeout, honeybeetest.TestTick)
 	})
 }
-
-func TestStartWriter(t *testing.T) {
-	t.Run("data from outgoing triggers write", func(t *testing.T) {
-		conn, _, _, outgoingData := setupTestConnection(t, nil)
-		defer conn.Close()
-
-		testData := []byte("test message")
-		err := conn.Send(testData)
-		assert.NoError(t, err)
-
-		honeybeetest.ExpectWrite(t, outgoingData, websocket.TextMessage, testData)
-	})
-
-	t.Run("multiple messages processed sequentially", func(t *testing.T) {
-		conn, _, _, outgoingData := setupTestConnection(t, nil)
-		defer conn.Close()
-
-		messages := [][]byte{[]byte("first"), []byte("second"), []byte("third")}
-		for _, msg := range messages {
-			err := conn.Send(msg)
-			assert.NoError(t, err)
-		}
-
-		for _, expected := range messages {
-			honeybeetest.ExpectWrite(t, outgoingData, websocket.TextMessage, expected)
-		}
-	})
-
-	t.Run("write timeout disabled when zero", func(t *testing.T) {
-		if testing.Short() {
-			t.Skip("skipping test in short mode")
-		}
-
-		config := &ConnectionConfig{WriteTimeout: 0}
-
-		outgoingData := make(chan honeybeetest.MockOutgoingData, 10)
-		mockSocket := honeybeetest.NewMockSocket()
-
-		mockSocket.CloseFunc = func() error {
-			mockSocket.Once.Do(func() {
-				close(mockSocket.Closed)
-			})
-			return nil
-		}
-
-		deadlineCalled := make(chan struct{}, 1)
-		mockSocket.SetWriteDeadlineFunc = func(t time.Time) error {
-			deadlineCalled <- struct{}{}
-			return nil
-		}
-
-		mockSocket.WriteMessageFunc = func(msgType int, data []byte) error {
-			select {
-			case outgoingData <- honeybeetest.MockOutgoingData{
-				MsgType: msgType, Data: data}:
-			case <-mockSocket.Closed:
-				return io.EOF
-			}
-			return nil
-		}
-
-		conn, err := NewConnectionFromSocket(mockSocket, config, nil)
-		assert.NoError(t, err)
-		defer conn.Close()
-
-		err = conn.Send([]byte("test"))
-		assert.NoError(t, err)
-
-		assert.Never(t, func() bool {
-			select {
-			case <-deadlineCalled:
-				return true
-			default:
-				return false
-			}
-		}, honeybeetest.NegativeTestTimeout, honeybeetest.TestTick,
-			"SetWriteDeadline should not be called when timeout is zero")
-	})
-
-	t.Run("write timeout sets deadline when positive", func(t *testing.T) {
-		config := &ConnectionConfig{WriteTimeout: 30 * time.Millisecond}
-
-		outgoingData := make(chan honeybeetest.MockOutgoingData, 10)
-		mockSocket := honeybeetest.NewMockSocket()
-
-		mockSocket.CloseFunc = func() error {
-			mockSocket.Once.Do(func() {
-				close(mockSocket.Closed)
-			})
-			return nil
-		}
-
-		deadlineCalled := make(chan struct{}, 1)
-		mockSocket.SetWriteDeadlineFunc = func(t time.Time) error {
-			deadlineCalled <- struct{}{}
-			return nil
-		}
-
-		mockSocket.WriteMessageFunc = func(msgType int, data []byte) error {
-			select {
-			case outgoingData <- honeybeetest.MockOutgoingData{
-				MsgType: msgType, Data: data}:
-			case <-mockSocket.Closed:
-				return io.EOF
-			}
-			return nil
-		}
-
-		conn, err := NewConnectionFromSocket(mockSocket, config, nil)
-		assert.NoError(t, err)
-		defer conn.Close()
-
-		err = conn.Send([]byte("test"))
-		assert.NoError(t, err)
-
-		assert.Eventually(t, func() bool {
-			select {
-			case <-deadlineCalled:
-				return true
-			default:
-				return false
-			}
-		}, honeybeetest.TestTimeout, honeybeetest.TestTick,
-			"SetWriteDeadline should be called when timeout is positive")
-	})
-
-	t.Run("writer exits on deadline error", func(t *testing.T) {
-		config := &ConnectionConfig{WriteTimeout: 1 * time.Millisecond}
-
-		mockSocket := honeybeetest.NewMockSocket()
-
-		mockSocket.CloseFunc = func() error {
-			mockSocket.Once.Do(func() {
-				close(mockSocket.Closed)
-			})
-			return nil
-		}
-
-		mockSocket.SetWriteDeadlineFunc = func(t time.Time) error {
-			return fmt.Errorf("test error")
-		}
-
-		conn, err := NewConnectionFromSocket(mockSocket, config, nil)
-		assert.NoError(t, err)
-
-		err = conn.Send([]byte("test"))
-		assert.NoError(t, err)
-		defer conn.Close()
-
-		assert.Eventually(t, func() bool {
-			select {
-			case err := <-conn.Errors():
-				return err != nil &&
-					strings.Contains(err.Error(), "failed to set write deadline")
-			default:
-				return false
-			}
-		}, honeybeetest.TestTimeout, honeybeetest.TestTick)
-
-		assert.Eventually(t, func() bool {
-			return conn.State() == StateClosed
-		}, honeybeetest.TestTimeout, honeybeetest.TestTick)
-	})
-
-	t.Run("writer exits on socket write error", func(t *testing.T) {
-		mockSocket := honeybeetest.NewMockSocket()
-
-		writeErr := fmt.Errorf("write failed")
-		mockSocket.WriteMessageFunc = func(msgType int, data []byte) error {
-			return writeErr
-		}
-
-		conn, err := NewConnectionFromSocket(mockSocket, nil, nil)
-		assert.NoError(t, err)
-		defer conn.Close()
-
-		err = conn.Send([]byte("test"))
-		assert.NoError(t, err)
-
-		assert.Eventually(t, func() bool {
-			select {
-			case err := <-conn.Errors():
-				return err == writeErr
-			default:
-				return false
-			}
-		}, honeybeetest.TestTimeout, honeybeetest.TestTick)
-
-		assert.Eventually(t, func() bool {
-			return conn.State() == StateClosed
-		}, honeybeetest.TestTimeout, honeybeetest.TestTick)
-	})
-}
-
-// Helpers
diff --git a/transport/connection_send_test.go b/transport/connection_send_test.go
index e5869d9..211a024 100644
--- a/transport/connection_send_test.go
+++ b/transport/connection_send_test.go
@@ -2,110 +2,243 @@ package transport
 
 import (
 	"fmt"
+	"git.wisehodl.dev/jay/go-honeybee/honeybeetest"
+	"github.com/gorilla/websocket"
 	"github.com/stretchr/testify/assert"
+	"io"
 	"sync"
 	"testing"
+	"time"
 )
 
 func TestConnectionSend(t *testing.T) {
-	cases := []struct {
-		name        string
-		setup       func(*Connection)
-		data        []byte
-		wantErr     bool
-		wantErrText string
-	}{
-		{
-			name:  "send succeeds when open",
-			setup: func(c *Connection) {},
-			data:  []byte("test message"),
-		},
-		{
-			name: "send fails when closed",
-			setup: func(c *Connection) {
-				c.Close()
-			},
-			data:        []byte("test"),
-			wantErr:     true,
-			wantErrText: "connection closed",
-		},
-		{
-			name: "send fails when queue full",
-			setup: func(c *Connection) {
-				// Fill outgoing channel
-				for i := 0; i < 100; i++ {
-					c.outgoing <- []byte("filler")
-				}
-			},
-			data:        []byte("overflow"),
-			wantErr:     true,
-			wantErrText: "outgoing queue full",
-		},
-	}
+	t.Run("writes message to socket", func(t *testing.T) {
+		conn, _, _, outgoingData := setupTestConnection(t, nil)
+		defer conn.Close()
 
-	for _, tc := range cases {
-		t.Run(tc.name, func(t *testing.T) {
-			conn, err := NewConnection("ws://test", nil, nil)
+		testData := []byte("test message")
+		err := conn.Send(testData)
+		assert.NoError(t, err)
+
+		honeybeetest.ExpectWrite(t, outgoingData, websocket.TextMessage, testData)
+	})
+
+	t.Run("writes multiple message to socket", func(t *testing.T) {
+		conn, _, _, outgoingData := setupTestConnection(t, nil)
+		defer conn.Close()
+
+		messages := [][]byte{[]byte("first"), []byte("second"), []byte("third")}
+		for _, msg := range messages {
+			err := conn.Send(msg)
 			assert.NoError(t, err)
-
-			tc.setup(conn)
-
-			err = conn.Send(tc.data)
-
-			if tc.wantErr {
-				assert.Error(t, err)
-				if tc.wantErrText != "" {
-					assert.ErrorContains(t, err, tc.wantErrText)
-				}
-				return
-			}
-
-			assert.NoError(t, err)
-
-			select {
-			case sent := <-conn.outgoing:
-				assert.Equal(t, tc.data, sent)
-			default:
-				t.Fatal("data not sent to outgoing channel")
-			}
-		})
-	}
-}
-
-// Run with `go test -race` to ensure no race conditions occur
-func TestConnectionSendConcurrent(t *testing.T) {
-	conn, err := NewConnection("ws://test", nil, nil)
-	assert.NoError(t, err)
-
-	// continuously consume outgoing channel in background
-	done := make(chan struct{})
-	go func() {
-		for {
-			select {
-			case <-conn.outgoing:
-			case <-done:
-				return
-			}
 		}
-	}()
-	defer close(done)
 
-	// Send from multiple goroutines concurrently
-	const goroutines = 5
-	const messagesPerGoroutine = 10
-	var wg sync.WaitGroup
+		for _, expected := range messages {
+			honeybeetest.ExpectWrite(t, outgoingData, websocket.TextMessage, expected)
+		}
+	})
 
-	for i := 0; i < goroutines; i++ {
-		wg.Add(1)
-		go func(id int) {
-			defer wg.Done()
-			for j := 0; j < messagesPerGoroutine; j++ {
-				data := []byte(fmt.Sprintf("msg-%d-%d", id, j))
-				err := conn.Send(data)
-				assert.NoError(t, err)
+	t.Run("concurrent sends write messages to socket", func(t *testing.T) {
+		conn, _, _, outgoingData := setupTestConnection(t, nil)
+		defer conn.Close()
+
+		mu := sync.Mutex{}
+		messages := []string{}
+		done := make(chan struct{})
+
+		go func() {
+			for {
+				select {
+				case msg := <-outgoingData:
+					fmt.Printf("got message %s\n", string(msg.Data))
+					mu.Lock()
+					messages = append(messages, string(msg.Data))
+					mu.Unlock()
+				case <-done:
+					return
+				}
 			}
-		}(i)
-	}
+		}()
 
-	wg.Wait()
+		defer close(done)
+
+		var wg sync.WaitGroup
+		for i := 0; i < 5; i++ {
+			wg.Add(1)
+			go func(id int) {
+				defer wg.Done()
+				for j := 0; j < 10; j++ {
+					data := []byte(fmt.Sprintf("msg-%d-%d", id, j))
+					fmt.Printf("sending message %s\n", string(data))
+					for {
+						// send and retry until success
+						err := conn.Send(data)
+						if err != nil {
+							continue
+						} else {
+							break
+						}
+					}
+				}
+			}(i)
+		}
+
+		wg.Wait()
+
+		assert.Eventually(t, func() bool {
+			mu.Lock()
+			defer mu.Unlock()
+			return len(messages) == 50
+		}, honeybeetest.TestTimeout, honeybeetest.TestTick,
+			"should have received 50 messages")
+
+	})
+
+	t.Run("send fails when connection is closed", func(t *testing.T) {
+		conn, _, _, _ := setupTestConnection(t, nil)
+		conn.Close()
+
+		testData := []byte("test message")
+		err := conn.Send(testData)
+		assert.ErrorIs(t, err, ErrConnectionClosed)
+	})
+
+	t.Run("write timeout disabled when zero", func(t *testing.T) {
+		config := &ConnectionConfig{WriteTimeout: 0}
+
+		outgoingData := make(chan honeybeetest.MockOutgoingData, 10)
+		mockSocket := honeybeetest.NewMockSocket()
+
+		mockSocket.CloseFunc = func() error {
+			mockSocket.Once.Do(func() {
+				close(mockSocket.Closed)
+			})
+			return nil
+		}
+
+		deadlineCalled := make(chan struct{}, 1)
+		mockSocket.SetWriteDeadlineFunc = func(t time.Time) error {
+			deadlineCalled <- struct{}{}
+			return nil
+		}
+
+		mockSocket.WriteMessageFunc = func(msgType int, data []byte) error {
+			select {
+			case outgoingData <- honeybeetest.MockOutgoingData{
+				MsgType: msgType, Data: data}:
+			case <-mockSocket.Closed:
+				return io.EOF
+			}
+			return nil
+		}
+
+		conn, err := NewConnectionFromSocket(mockSocket, config, nil)
+		assert.NoError(t, err)
+		defer conn.Close()
+
+		err = conn.Send([]byte("test"))
+		assert.NoError(t, err)
+
+		assert.Never(t, func() bool {
+			select {
+			case <-deadlineCalled:
+				return true
+			default:
+				return false
+			}
+		}, honeybeetest.NegativeTestTimeout, honeybeetest.TestTick,
+			"SetWriteDeadline should not be called when timeout is zero")
+	})
+
+	t.Run("write timeout sets deadline when positive", func(t *testing.T) {
+		config := &ConnectionConfig{WriteTimeout: 30 * time.Millisecond}
+
+		outgoingData := make(chan honeybeetest.MockOutgoingData, 10)
+		mockSocket := honeybeetest.NewMockSocket()
+
+		mockSocket.CloseFunc = func() error {
+			mockSocket.Once.Do(func() {
+				close(mockSocket.Closed)
+			})
+			return nil
+		}
+
+		deadlineCalled := make(chan struct{}, 1)
+		mockSocket.SetWriteDeadlineFunc = func(t time.Time) error {
+			deadlineCalled <- struct{}{}
+			return nil
+		}
+
+		mockSocket.WriteMessageFunc = func(msgType int, data []byte) error {
+			select {
+			case outgoingData <- honeybeetest.MockOutgoingData{
+				MsgType: msgType, Data: data}:
+			case <-mockSocket.Closed:
+				return io.EOF
+			}
+			return nil
+		}
+
+		conn, err := NewConnectionFromSocket(mockSocket, config, nil)
+		assert.NoError(t, err)
+		defer conn.Close()
+
+		err = conn.Send([]byte("test"))
+		assert.NoError(t, err)
+
+		assert.Eventually(t, func() bool {
+			select {
+			case <-deadlineCalled:
+				return true
+			default:
+				return false
+			}
+		}, honeybeetest.TestTimeout, honeybeetest.TestTick,
+			"SetWriteDeadline should be called when timeout is positive")
+	})
+
+	t.Run("send fails on deadline error", func(t *testing.T) {
+		config := &ConnectionConfig{WriteTimeout: 1 * time.Millisecond}
+
+		mockSocket := honeybeetest.NewMockSocket()
+
+		mockSocket.CloseFunc = func() error {
+			mockSocket.Once.Do(func() {
+				close(mockSocket.Closed)
+			})
+			return nil
+		}
+
+		mockSocket.SetWriteDeadlineFunc = func(t time.Time) error {
+			return fmt.Errorf("test error")
+		}
+
+		conn, err := NewConnectionFromSocket(mockSocket, config, nil)
+		assert.NoError(t, err)
+		defer conn.Close()
+
+		err = conn.Send([]byte("test"))
+		assert.ErrorContains(t, err, "failed to set write deadline: test error")
+
+		assert.Eventually(t, func() bool {
+			return conn.State() == StateClosed
+		}, honeybeetest.TestTimeout, honeybeetest.TestTick)
+	})
+
+	t.Run("send fails on socket write error", func(t *testing.T) {
+		mockSocket := honeybeetest.NewMockSocket()
+
+		writeErr := fmt.Errorf("test error")
+		mockSocket.WriteMessageFunc = func(msgType int, data []byte) error {
+			return writeErr
+		}
+
+		conn, err := NewConnectionFromSocket(mockSocket, nil, nil)
+		assert.NoError(t, err)
+		defer conn.Close()
+
+		err = conn.Send([]byte("test"))
+		assert.ErrorIs(t, err, ErrWriteFailed)
+		assert.ErrorContains(t, err, "test error")
+	})
 }
diff --git a/transport/connection_test.go b/transport/connection_test.go
index d02f4b0..25d0ad9 100644
--- a/transport/connection_test.go
+++ b/transport/connection_test.go
@@ -112,7 +112,6 @@ func TestNewConnection(t *testing.T) {
 			assert.Nil(t, conn.socket)
 			assert.NotNil(t, conn.config)
 			assert.NotNil(t, conn.incoming)
-			assert.NotNil(t, conn.outgoing)
 			assert.NotNil(t, conn.errors)
 			assert.NotNil(t, conn.done)
 			assert.Equal(t, StateDisconnected, conn.state)
@@ -213,7 +212,6 @@ func TestNewConnectionFromSocket(t *testing.T) {
 			assert.Equal(t, tc.socket, conn.socket)
 			assert.NotNil(t, conn.config)
 			assert.NotNil(t, conn.incoming)
-			assert.NotNil(t, conn.outgoing)
 			assert.NotNil(t, conn.errors)
 			assert.NotNil(t, conn.done)
 			assert.Equal(t, StateConnected, conn.state)
diff --git a/transport/errors.go b/transport/errors.go
index bcc01dc..b176568 100644
--- a/transport/errors.go
+++ b/transport/errors.go
@@ -13,6 +13,10 @@ var (
 	InvalidRetryInitialDelay = errors.New("initial delay must be positive")
 	InvalidRetryMaxDelay     = errors.New("max delay must be positive")
 	InvalidRetryJitterFactor = errors.New("jitter factor must be between 0.0 and 1.0")
+
+	// Connection Errors
+	ErrConnectionClosed = errors.New("connection closed")
+	ErrWriteFailed      = errors.New("write failed")
 )
 
 func NewConfigError(text string) error {
diff --git a/transport/logging_test.go b/transport/logging_test.go
index e55f926..a103668 100644
--- a/transport/logging_test.go
+++ b/transport/logging_test.go
@@ -413,7 +413,7 @@ func TestWriterLogging(t *testing.T) {
 		assert.NoError(t, err)
 
 		err = conn.Send([]byte("test"))
-		assert.NoError(t, err)
+		assert.ErrorContains(t, err, "failed to set write deadline: deadline error")
 
 		assert.Eventually(t, func() bool {
 			return findLogRecord(
@@ -443,7 +443,7 @@ func TestWriterLogging(t *testing.T) {
 		assert.NoError(t, err)
 
 		err = conn.Send([]byte("test"))
-		assert.NoError(t, err)
+		assert.ErrorContains(t, err, "write error")
 
 		assert.Eventually(t, func() bool {
 			return findLogRecord(
diff --git a/transport/socket_test.go b/transport/socket_test.go
index ffa2553..1c5dc95 100644
--- a/transport/socket_test.go
+++ b/transport/socket_test.go
@@ -199,9 +199,9 @@ func TestAcquireSocketContextCancellation(t *testing.T) {
 				done <- err
 			}()
 
-			// wait for first dial to complete, then cancel during sleep
+			// wait for first two dials to complete, then cancel during sleep
 			assert.Eventually(t, func() bool {
-				return dialCount.Load() >= 1
+				return dialCount.Load() > 1
 			}, honeybeetest.TestTimeout, honeybeetest.TestTick)
 			cancel()