diff --git a/initiatorpool/errors.go b/initiatorpool/errors.go
index 8dfb8b4..a20fcff 100644
--- a/initiatorpool/errors.go
+++ b/initiatorpool/errors.go
@@ -17,8 +17,8 @@ var (
 	ErrConnectionUnavailable = errors.New("connection unavailable")
 )
 
-func NewConfigError(text string) error {
-	return fmt.Errorf("configuration error: %s", text)
+func NewConfigError(err error) error {
+	return fmt.Errorf("configuration error: %w", err)
 }
 
 func NewPoolError(err error) error {
diff --git a/initiatorpool/worker_session_inner_test.go b/initiatorpool/worker_session_inner_test.go
index f86fea1..bcb6f01 100644
--- a/initiatorpool/worker_session_inner_test.go
+++ b/initiatorpool/worker_session_inner_test.go
@@ -125,7 +125,7 @@ func TestRunReader(t *testing.T) {
 		incomingData <- honeybeetest.MockIncomingData{Err: io.EOF}
 
 		err := <-conn.Errors()
-		assert.Equal(t, io.EOF, err)
+		assert.ErrorIs(t, err, io.EOF)
 
 		honeybeetest.Eventually(t, func() bool {
 			return conn.State() == transport.StateClosed
diff --git a/transport/config.go b/transport/config.go
index 0ff5be2..13c3a9b 100644
--- a/transport/config.go
+++ b/transport/config.go
@@ -86,7 +86,7 @@ func ValidateConnectionConfig(config *ConnectionConfig) error {
 		}
 
 		if config.Retry.InitialDelay > config.Retry.MaxDelay {
-			return NewConfigError("initial delay may not exceed maximum delay")
+			return NewConfigError(InvalidDelays)
 		}
 	}
 
diff --git a/transport/connection.go b/transport/connection.go
index c2e0c75..41a5273 100644
--- a/transport/connection.go
+++ b/transport/connection.go
@@ -91,7 +91,7 @@ func NewConnectionFromSocket(
 	socket types.Socket, config *ConnectionConfig, logger *slog.Logger,
 ) (*Connection, error) {
 	if socket == nil {
-		return nil, NewConnectionError("socket cannot be nil")
+		return nil, NewConnectionError(ErrNilSocket)
 	}
 
 	if config == nil {
@@ -128,11 +128,11 @@ func (c *Connection) Connect(ctx context.Context) error {
 	defer c.mu.Unlock()
 
 	if c.socket != nil {
-		return NewConnectionError("connection already has socket")
+		return NewConnectionError(ErrSocketExists)
 	}
 
 	if c.closed {
-		return NewConnectionError("connection is closed")
+		return NewConnectionError(ErrConnectionClosed)
 	}
 
 	if c.logger != nil {
@@ -150,7 +150,7 @@ func (c *Connection) Connect(ctx context.Context) error {
 		if c.logger != nil {
 			c.logger.Error("connection failed", "error", err)
 		}
-		return err
+		return NewConnectionError(err)
 	}
 
 	c.socket = socket
@@ -217,7 +217,7 @@ func (c *Connection) shutdownSetClosed(wait bool) error {
 	c.mu.Lock()
 	if c.closed {
 		c.mu.Unlock()
-		return ErrConnectionClosed
+		return NewConnectionError(ErrConnectionClosed)
 	}
 	c.closed = true
 	c.state = StateClosed
@@ -277,29 +277,37 @@ func (c *Connection) startReader() {
 			default:
 				messageType, data, err := c.socket.ReadMessage()
 				if err != nil {
-					if c.logger != nil {
-						var closeErr *websocket.CloseError
-						if errors.As(err, &closeErr) {
-							switch closeErr.Code {
-							case websocket.CloseNormalClosure, websocket.CloseGoingAway:
+					var wrappedErr error
+					var closeErr *websocket.CloseError
+					if errors.As(err, &closeErr) {
+						switch closeErr.Code {
+						case websocket.CloseNormalClosure, websocket.CloseGoingAway:
+							if c.logger != nil {
 								c.logger.Info("connection closed by peer",
 									"code", closeErr.Code,
 									"text", closeErr.Text,
 								)
-							default:
+							}
+							wrappedErr = fmt.Errorf("%w: %w", ErrPeerClosedClean, err)
+						default:
+							if c.logger != nil {
 								c.logger.Error("unexpected close",
 									"code", closeErr.Code,
 									"text", closeErr.Text,
 								)
 							}
-						} else {
+							wrappedErr = fmt.Errorf("%w: %w", ErrPeerClosedUnexpected, err)
+						}
+					} else {
+						if c.logger != nil {
 							c.logger.Error("read error", "error", err)
 						}
+						wrappedErr = fmt.Errorf("%w: %w", ErrReadError, err)
 					}
 
 					select {
 					case <-c.done:
-					case c.errors <- err:
+					case c.errors <- wrappedErr:
 					}
 					return
 				}
@@ -316,7 +324,6 @@ func (c *Connection) startReader() {
 			}
 		}
 	}()
-
 }
 
 func (c *Connection) Send(data []byte) error {
@@ -324,7 +331,7 @@ func (c *Connection) Send(data []byte) error {
 	defer c.writeMu.Unlock()
 
 	if c.closed {
-		return ErrConnectionClosed
+		return NewConnectionError(ErrConnectionClosed)
 	}
 
 	if c.config.WriteTimeout > 0 {
@@ -333,7 +340,7 @@ func (c *Connection) Send(data []byte) error {
 				c.logger.Error("write deadline error", "error", err)
 			}
 			c.shutdownExternal()
-			return fmt.Errorf("failed to set write deadline: %w", err)
+			return NewConnectionError(fmt.Errorf("%w: %w", ErrFailedWriteDeadline, err))
 		}
 	}
 
@@ -341,7 +348,7 @@ func (c *Connection) Send(data []byte) error {
 		if c.logger != nil {
 			c.logger.Error("write error", "error", err)
 		}
-		return fmt.Errorf("%w: %w", ErrWriteFailed, err)
+		return NewConnectionError(fmt.Errorf("%w: %w", ErrWriteFailed, err))
 	}
 
 	return nil
diff --git a/transport/connection_close_test.go b/transport/connection_close_test.go
index e6e5405..fbd2206 100644
--- a/transport/connection_close_test.go
+++ b/transport/connection_close_test.go
@@ -73,7 +73,7 @@ func TestDisconnectedConnectionClose(t *testing.T) {
 
 		err = conn.Send([]byte("test"))
 		assert.Error(t, err)
-		assert.ErrorContains(t, err, "connection closed")
+		assert.ErrorIs(t, err, ErrConnectionClosed)
 	})
 
 }
diff --git a/transport/connection_send_test.go b/transport/connection_send_test.go
index 7cf64f1..d556eec 100644
--- a/transport/connection_send_test.go
+++ b/transport/connection_send_test.go
@@ -213,7 +213,7 @@ func TestConnectionSend(t *testing.T) {
 		defer conn.Close()
 
 		err = conn.Send([]byte("test"))
-		assert.ErrorContains(t, err, "failed to set write deadline: test error")
+		assert.ErrorIs(t, err, ErrFailedWriteDeadline)
 
 		honeybeetest.Eventually(t, func() bool {
 			return conn.State() == StateClosed
diff --git a/transport/connection_test.go b/transport/connection_test.go
index 8c7f8e6..95cc1b9 100644
--- a/transport/connection_test.go
+++ b/transport/connection_test.go
@@ -3,9 +3,11 @@ package transport
 import (
 	"bytes"
 	"context"
+	"errors"
 	"fmt"
 	"git.wisehodl.dev/jay/go-honeybee/honeybeetest"
 	"git.wisehodl.dev/jay/go-honeybee/types"
+	"github.com/gorilla/websocket"
 	"github.com/stretchr/testify/assert"
 	"io"
 	"net/http"
@@ -241,7 +243,7 @@ func TestConnect(t *testing.T) {
 
 		err = conn.Connect(context.Background())
 		assert.Error(t, err)
-		assert.ErrorContains(t, err, "already has socket")
+		assert.ErrorIs(t, err, ErrSocketExists)
 		assert.Equal(t, StateDisconnected, conn.State())
 	})
 
@@ -253,7 +255,7 @@ func TestConnect(t *testing.T) {
 
 		err = conn.Connect(context.Background())
 		assert.Error(t, err)
-		assert.ErrorContains(t, err, "connection is closed")
+		assert.ErrorIs(t, err, ErrConnectionClosed)
 		assert.Equal(t, StateClosed, conn.State())
 	})
 
@@ -467,17 +469,72 @@ func TestConnectionIncoming(t *testing.T) {
 }
 
 func TestConnectionErrors(t *testing.T) {
-	conn, err := NewConnection("ws://test", nil, nil)
-	assert.NoError(t, err)
+	t.Run("clean close by peer", func(t *testing.T) {
+		mockSocket := honeybeetest.NewMockSocket()
+		mockSocket.ReadMessageFunc = func() (int, []byte, error) {
+			return 0, nil, &websocket.CloseError{
+				Code: websocket.CloseNormalClosure,
+				Text: "goodbye",
+			}
+		}
 
-	errors := conn.Errors()
-	assert.NotNil(t, errors)
+		conn, err := NewConnectionFromSocket(mockSocket, nil, nil)
+		assert.NoError(t, err)
+		defer conn.Close()
 
-	// send data through the channel to verify they are the same
-	testErr := fmt.Errorf("test error")
-	conn.errors <- testErr
-	received := <-errors
-	assert.Equal(t, testErr, received)
+		honeybeetest.Eventually(t, func() bool {
+			select {
+			case err := <-conn.Errors():
+				return errors.Is(err, ErrPeerClosedClean)
+			default:
+				return false
+			}
+		}, "expected clean close error")
+	})
+
+	t.Run("unexpected close", func(t *testing.T) {
+		mockSocket := honeybeetest.NewMockSocket()
+		mockSocket.ReadMessageFunc = func() (int, []byte, error) {
+			return 0, nil, &websocket.CloseError{
+				Code: websocket.CloseProtocolError,
+				Text: "bad protocol",
+			}
+		}
+
+		conn, err := NewConnectionFromSocket(mockSocket, nil, nil)
+		assert.NoError(t, err)
+		defer conn.Close()
+
+		honeybeetest.Eventually(t, func() bool {
+			select {
+			case err := <-conn.Errors():
+				return errors.Is(err, ErrPeerClosedUnexpected)
+			default:
+				return false
+			}
+		}, "expected unexpected close error")
+	})
+
+	t.Run("read error", func(t *testing.T) {
+		mockSocket := honeybeetest.NewMockSocket()
+		mockSocket.ReadMessageFunc = func() (int, []byte, error) {
+			return 0, nil, io.EOF
+		}
+
+		conn, err := NewConnectionFromSocket(mockSocket, nil, nil)
+		assert.NoError(t, err)
+		defer conn.Close()
+
+		honeybeetest.Eventually(t, func() bool {
+			select {
+			case err := <-conn.Errors():
+				return errors.Is(err, ErrReadError)
+			default:
+				return false
+			}
+		}, "expected read error")
+
+	})
 }
 
 // Test helpers
diff --git a/transport/errors.go b/transport/errors.go
index b176568..84c1bd0 100644
--- a/transport/errors.go
+++ b/transport/errors.go
@@ -13,16 +13,28 @@ 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")
+	InvalidDelays            = errors.New("initial delay may not exceed maximum delay")
+
+	// Socket Errors
+	ErrNilRetryManager = errors.New("retry manager cannot be nil")
+	ErrNilDialer       = errors.New("dialer cannot be nil")
+	ErrEmptyURL        = errors.New("URL cannot be empty")
 
 	// Connection Errors
-	ErrConnectionClosed = errors.New("connection closed")
-	ErrWriteFailed      = errors.New("write failed")
+	ErrConnectionClosed     = errors.New("connection closed")
+	ErrWriteFailed          = errors.New("write failed")
+	ErrNilSocket            = errors.New("socket cannot be nil")
+	ErrSocketExists         = errors.New("socket already exists")
+	ErrFailedWriteDeadline  = errors.New("failed to set write deadline")
+	ErrPeerClosedClean      = errors.New("peer closed connection cleanly")
+	ErrPeerClosedUnexpected = errors.New("peer closed connection unexpectedly")
+	ErrReadError            = errors.New("read error")
 )
 
-func NewConfigError(text string) error {
-	return fmt.Errorf("configuration error: %s", text)
+func NewConfigError(err error) error {
+	return fmt.Errorf("configuration error: %w", err)
 }
 
-func NewConnectionError(text string) error {
-	return fmt.Errorf("connection error: %s", text)
+func NewConnectionError(err error) error {
+	return fmt.Errorf("connection error: %w", err)
 }
diff --git a/transport/socket.go b/transport/socket.go
index e13debf..7eaf327 100644
--- a/transport/socket.go
+++ b/transport/socket.go
@@ -54,13 +54,13 @@ func AcquireSocket(
 	}
 
 	if retryMgr == nil {
-		return nil, nil, NewConnectionError("retry manager cannot be nil")
+		return nil, nil, NewConnectionError(ErrNilRetryManager)
 	}
 	if dialer == nil {
-		return nil, nil, NewConnectionError("dialer cannot be nil")
+		return nil, nil, NewConnectionError(ErrNilDialer)
 	}
 	if url == "" {
-		return nil, nil, NewConnectionError("URL cannot be empty")
+		return nil, nil, NewConnectionError(ErrEmptyURL)
 	}
 
 	for {