diff --git a/port_forwarding.go b/port_forwarding.go
index dee7b2a919..278fae4e24 100644
--- a/port_forwarding.go
+++ b/port_forwarding.go
@@ -2,6 +2,7 @@ package testcontainers
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"io"
 	"net"
@@ -231,12 +232,14 @@ func (sshdC *sshdContainer) exposeHostPort(ctx context.Context, ports ...int) er
 		go pw.Forward(ctx)
 	}
 
+	var err error
+
 	// continue when all port forwarders have created the connection
 	for _, pfw := range sshdC.portForwarders {
-		<-pfw.connectionCreated
+		err = errors.Join(err, <-pfw.connectionCreated)
 	}
 
-	return nil
+	return err
 }
 
 type PortForwarder struct {
@@ -244,7 +247,7 @@ type PortForwarder struct {
 	sshConfig         *ssh.ClientConfig
 	remotePort        int
 	localPort         int
-	connectionCreated chan struct{} // used to signal that the connection has been created, so the caller can proceed
+	connectionCreated chan error    // used to signal that the connection has been created, so the caller can proceed
 	terminateChan     chan struct{} // used to signal that the connection has been terminated
 }
 
@@ -254,7 +257,7 @@ func NewPortForwarder(sshDAddr string, sshConfig *ssh.ClientConfig, remotePort,
 		sshConfig:         sshConfig,
 		remotePort:        remotePort,
 		localPort:         localPort,
-		connectionCreated: make(chan struct{}),
+		connectionCreated: make(chan error),
 		terminateChan:     make(chan struct{}),
 	}
 }
@@ -267,18 +270,22 @@ func (pf *PortForwarder) Close(ctx context.Context) {
 func (pf *PortForwarder) Forward(ctx context.Context) error {
 	client, err := ssh.Dial("tcp", pf.sshDAddr, pf.sshConfig)
 	if err != nil {
-		return fmt.Errorf("error dialing ssh server: %w", err)
+		err = fmt.Errorf("error dialing ssh server: %w", err)
+		pf.connectionCreated <- err
+		return err
 	}
 	defer client.Close()
 
 	listener, err := client.Listen("tcp", fmt.Sprintf("localhost:%d", pf.remotePort))
 	if err != nil {
-		return fmt.Errorf("error listening on remote port: %w", err)
+		err = fmt.Errorf("error listening on remote port: %w", err)
+		pf.connectionCreated <- err
+		return err
 	}
 	defer listener.Close()
 
 	// signal that the connection has been created
-	pf.connectionCreated <- struct{}{}
+	pf.connectionCreated <- nil
 
 	// check if the context or the terminateChan has been closed
 	select {