diff --git a/downstream.go b/downstream.go
index 1496ce2..96ee7b3 100644
--- a/downstream.go
+++ b/downstream.go
@@ -244,6 +244,8 @@ func (dc *downstreamConn) readMessages(ch chan<- event) error {
 }
 
 func (dc *downstreamConn) writeMessages() error {
+	// TODO: any SendMessage call after the connection is closed will
+	// either block or drop
 	for {
 		var err error
 		var closed bool
@@ -252,6 +254,7 @@ func (dc *downstreamConn) writeMessages() error {
 			if dc.srv.Debug {
 				dc.logger.Printf("sent: %v", msg)
 			}
+			dc.net.SetWriteDeadline(time.Now().Add(writeTimeout))
 			err = dc.irc.WriteMessage(msg)
 		case <-dc.closed:
 			closed = true
diff --git a/server.go b/server.go
index 0ebd1c8..94af998 100644
--- a/server.go
+++ b/server.go
@@ -13,6 +13,7 @@ import (
 // TODO: make configurable
 var keepAlivePeriod = time.Minute
 var retryConnectMinDelay = time.Minute
+var writeTimeout = 10 * time.Second
 
 func setKeepAlive(c net.Conn) error {
 	tcpConn, ok := c.(*net.TCPConn)
diff --git a/upstream.go b/upstream.go
index 341dc03..2c430aa 100644
--- a/upstream.go
+++ b/upstream.go
@@ -111,6 +111,8 @@ func connectToUpstream(network *network) (*upstreamConn, error) {
 	}
 
 	go func() {
+		// TODO: any SendMessage call after the connection is closed will
+		// either block or drop
 		for {
 			var closed bool
 			select {
@@ -118,8 +120,10 @@ func connectToUpstream(network *network) (*upstreamConn, error) {
 				if uc.srv.Debug {
 					uc.logger.Printf("sent: %v", msg)
 				}
+				uc.net.SetWriteDeadline(time.Now().Add(writeTimeout))
 				if err := uc.irc.WriteMessage(msg); err != nil {
 					uc.logger.Printf("failed to write message: %v", err)
+					closed = true
 				}
 			case <-uc.closed:
 				closed = true