diff --git a/dialer.go b/dialer.go
index a8e4c1893..de4419ff8 100644
--- a/dialer.go
+++ b/dialer.go
@@ -25,7 +25,7 @@ import (
 	"github.com/quickfixgo/quickfix/config"
 )
 
-func loadDialerConfig(settings *SessionSettings) (dialer proxy.Dialer, err error) {
+func loadDialerConfig(settings *SessionSettings) (dialer proxy.ContextDialer, err error) {
 	stdDialer := &net.Dialer{}
 	if settings.HasSetting(config.SocketTimeout) {
 		timeout, err := settings.DurationSetting(config.SocketTimeout)
@@ -73,9 +73,23 @@ func loadDialerConfig(settings *SessionSettings) (dialer proxy.Dialer, err error
 			}
 		}
 
-		dialer, err = proxy.SOCKS5("tcp", fmt.Sprintf("%s:%d", proxyHost, proxyPort), proxyAuth, dialer)
+		var proxyDialer proxy.Dialer
+
+		proxyDialer, err = proxy.SOCKS5("tcp", fmt.Sprintf("%s:%d", proxyHost, proxyPort), proxyAuth, stdDialer)
+		if err != nil {
+			return
+		}
+
+		if contextDialer, ok := proxyDialer.(proxy.ContextDialer); ok {
+			dialer = contextDialer
+		} else {
+			err = fmt.Errorf("proxy does not support context dialer")
+			return
+		}
+
 	default:
 		err = fmt.Errorf("unsupported proxy type %s", proxyType)
 	}
+
 	return
 }
diff --git a/initiator.go b/initiator.go
index 8f7a76200..18451477e 100644
--- a/initiator.go
+++ b/initiator.go
@@ -17,6 +17,7 @@ package quickfix
 
 import (
 	"bufio"
+	"context"
 	"crypto/tls"
 	"strings"
 	"sync"
@@ -50,7 +51,7 @@ func (i *Initiator) Start() (err error) {
 			return
 		}
 
-		var dialer proxy.Dialer
+		var dialer proxy.ContextDialer
 		if dialer, err = loadDialerConfig(settings); err != nil {
 			return
 		}
@@ -142,7 +143,7 @@ func (i *Initiator) waitForReconnectInterval(reconnectInterval time.Duration) bo
 	return true
 }
 
-func (i *Initiator) handleConnection(session *session, tlsConfig *tls.Config, dialer proxy.Dialer) {
+func (i *Initiator) handleConnection(session *session, tlsConfig *tls.Config, dialer proxy.ContextDialer) {
 	var wg sync.WaitGroup
 	wg.Add(1)
 	go func() {
@@ -162,6 +163,19 @@ func (i *Initiator) handleConnection(session *session, tlsConfig *tls.Config, di
 			return
 		}
 
+		ctx, cancel := context.WithCancel(context.Background())
+
+		// We start a goroutine in order to be able to cancel the dialer mid-connection
+		// on receiving a stop signal to stop the initiator.
+		go func() {
+			select {
+			case <-i.stopChan:
+				cancel()
+			case <-ctx.Done():
+				return
+			}
+		}()
+
 		var disconnected chan interface{}
 		var msgIn chan fixIn
 		var msgOut chan []byte
@@ -169,7 +183,7 @@ func (i *Initiator) handleConnection(session *session, tlsConfig *tls.Config, di
 		address := session.SocketConnectAddress[connectionAttempt%len(session.SocketConnectAddress)]
 		session.log.OnEventf("Connecting to: %v", address)
 
-		netConn, err := dialer.Dial("tcp", address)
+		netConn, err := dialer.DialContext(ctx, "tcp", address)
 		if err != nil {
 			session.log.OnEventf("Failed to connect: %v", err)
 			goto reconnect
@@ -208,6 +222,10 @@ func (i *Initiator) handleConnection(session *session, tlsConfig *tls.Config, di
 			close(disconnected)
 		}()
 
+		// This ensures we properly cleanup the goroutine and context used for
+		// dial cancelation after successful connection.
+		cancel()
+
 		select {
 		case <-disconnected:
 		case <-i.stopChan:
@@ -215,6 +233,8 @@ func (i *Initiator) handleConnection(session *session, tlsConfig *tls.Config, di
 		}
 
 	reconnect:
+		cancel()
+
 		connectionAttempt++
 		session.log.OnEventf("Reconnecting in %v", session.ReconnectInterval)
 		if !i.waitForReconnectInterval(session.ReconnectInterval) {