diff --git a/conn.go b/conn.go
index 7b210cd..04b1237 100644
--- a/conn.go
+++ b/conn.go
@@ -217,14 +217,20 @@ func (c *conn) ReadMessage() (*irc.Message, error) {
 //
 // If the connection is closed before the message is sent, SendMessage silently
 // drops the message.
-func (c *conn) SendMessage(msg *irc.Message) {
+func (c *conn) SendMessage(ctx context.Context, msg *irc.Message) {
 	c.lock.Lock()
 	defer c.lock.Unlock()
 
 	if c.closed {
 		return
 	}
-	c.outgoing <- msg
+
+	select {
+	case c.outgoing <- msg:
+		// Success
+	case <-ctx.Done():
+		c.logger.Printf("failed to send message: %v", ctx.Err())
+	}
 }
 
 func (c *conn) RemoteAddr() net.Addr {
diff --git a/downstream.go b/downstream.go
index 6efe756..5bbfcb7 100644
--- a/downstream.go
+++ b/downstream.go
@@ -551,7 +551,7 @@ func (dc *downstreamConn) SendMessage(msg *irc.Message) {
 	}
 
 	dc.srv.metrics.downstreamOutMessagesTotal.Inc()
-	dc.conn.SendMessage(msg)
+	dc.conn.SendMessage(context.TODO(), msg)
 }
 
 func (dc *downstreamConn) SendBatch(typ string, params []string, tags irc.Tags, f func(batchRef irc.TagValue)) {
@@ -1666,7 +1666,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 			if upstream != nil && upstream != uc {
 				return
 			}
-			uc.SendMessageLabeled(dc.id, &irc.Message{
+			uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 				Command: "NICK",
 				Params:  []string{nick},
 			})
@@ -1700,7 +1700,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 			// We only need to call updateNetwork for upstreams that don't
 			// support setname
 			if uc := n.conn; uc != nil && uc.caps["setname"] {
-				uc.SendMessageLabeled(dc.id, &irc.Message{
+				uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 					Command: "SETNAME",
 					Params:  []string{realname},
 				})
@@ -1775,7 +1775,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 			if key != "" {
 				params = append(params, key)
 			}
-			uc.SendMessageLabeled(dc.id, &irc.Message{
+			uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 				Command: "JOIN",
 				Params:  params,
 			})
@@ -1835,7 +1835,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 				if reason != "" {
 					params = append(params, reason)
 				}
-				uc.SendMessageLabeled(dc.id, &irc.Message{
+				uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 					Command: "PART",
 					Params:  params,
 				})
@@ -1896,7 +1896,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 			if reason != "" {
 				params = append(params, reason)
 			}
-			uc.SendMessageLabeled(dc.id, &irc.Message{
+			uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 				Command: "KICK",
 				Params:  params,
 			})
@@ -1915,7 +1915,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 		if casemapASCII(name) == dc.nickCM {
 			if modeStr != "" {
 				if uc := dc.upstream(); uc != nil {
-					uc.SendMessageLabeled(dc.id, &irc.Message{
+					uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 						Command: "MODE",
 						Params:  []string{uc.nick, modeStr},
 					})
@@ -1956,7 +1956,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 		if modeStr != "" {
 			params := []string{upstreamName, modeStr}
 			params = append(params, msg.Params[2:]...)
-			uc.SendMessageLabeled(dc.id, &irc.Message{
+			uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 				Command: "MODE",
 				Params:  params,
 			})
@@ -2005,7 +2005,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 
 		if len(msg.Params) > 1 { // setting topic
 			topic := msg.Params[1]
-			uc.SendMessageLabeled(dc.id, &irc.Message{
+			uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 				Command: "TOPIC",
 				Params:  []string{upstreamName, topic},
 			})
@@ -2070,7 +2070,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 				sendNames(dc, ch)
 			} else {
 				// NAMES on a channel we have not joined, ask upstream
-				uc.SendMessageLabeled(dc.id, &irc.Message{
+				uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 					Command: "NAMES",
 					Params:  []string{upstreamName},
 				})
@@ -2270,7 +2270,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 			params = []string{upstreamNick}
 		}
 
-		uc.SendMessageLabeled(dc.id, &irc.Message{
+		uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 			Command: "WHOIS",
 			Params:  params,
 		})
@@ -2347,7 +2347,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 			if uc.isChannel(upstreamName) {
 				unmarshaledText = dc.unmarshalText(uc, text)
 			}
-			uc.SendMessageLabeled(dc.id, &irc.Message{
+			uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 				Tags:    tags,
 				Command: msg.Command,
 				Params:  []string{upstreamName, unmarshaledText},
@@ -2398,7 +2398,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 				continue
 			}
 
-			uc.SendMessageLabeled(dc.id, &irc.Message{
+			uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 				Tags:    tags,
 				Command: "TAGMSG",
 				Params:  []string{upstreamName},
@@ -2430,7 +2430,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 		}
 		uc := ucChannel
 
-		uc.SendMessageLabeled(dc.id, &irc.Message{
+		uc.SendMessageLabeled(ctx, dc.id, &irc.Message{
 			Command: "INVITE",
 			Params:  []string{upstreamUser, upstreamChannel},
 		})
@@ -2850,7 +2850,7 @@ func (dc *downstreamConn) handleMessageRegistered(ctx context.Context, msg *irc.
 			return newUnknownCommandError(msg.Command)
 		}
 
-		uc.SendMessageLabeled(dc.id, msg)
+		uc.SendMessageLabeled(ctx, dc.id, msg)
 	}
 	return nil
 }
diff --git a/service.go b/service.go
index 0d6d7f0..80fb261 100644
--- a/service.go
+++ b/service.go
@@ -616,7 +616,7 @@ func handleServiceNetworkQuote(ctx context.Context, dc *downstreamConn, params [
 	if err != nil {
 		return fmt.Errorf("failed to parse command %q: %v", params[1], err)
 	}
-	uc.SendMessage(m)
+	uc.SendMessage(ctx, m)
 
 	sendServicePRIVMSG(dc, fmt.Sprintf("sent command to %q", net.GetName()))
 	return nil
diff --git a/upstream.go b/upstream.go
index 1a454d3..6277a3b 100644
--- a/upstream.go
+++ b/upstream.go
@@ -342,7 +342,7 @@ func (uc *upstreamConn) sendNextPendingCommand(cmd string) {
 	if len(uc.pendingCmds[cmd]) == 0 {
 		return
 	}
-	uc.SendMessage(uc.pendingCmds[cmd][0].msg)
+	uc.SendMessage(context.TODO(), uc.pendingCmds[cmd][0].msg)
 }
 
 func (uc *upstreamConn) enqueueCommand(dc *downstreamConn, msg *irc.Message) {
@@ -450,7 +450,7 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 
 	switch msg.Command {
 	case "PING":
-		uc.SendMessage(&irc.Message{
+		uc.SendMessage(ctx, &irc.Message{
 			Command: "PONG",
 			Params:  msg.Params,
 		})
@@ -529,7 +529,7 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 				break // we'll send CAP END after authentication is completed
 			}
 
-			uc.SendMessage(&irc.Message{
+			uc.SendMessage(ctx, &irc.Message{
 				Command: "CAP",
 				Params:  []string{"END"},
 			})
@@ -583,7 +583,7 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 		// TODO: if a challenge is 400 bytes long, buffer it
 		var challengeStr string
 		if err := parseMessageParams(msg, &challengeStr); err != nil {
-			uc.SendMessage(&irc.Message{
+			uc.SendMessage(ctx, &irc.Message{
 				Command: "AUTHENTICATE",
 				Params:  []string{"*"},
 			})
@@ -595,7 +595,7 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 			var err error
 			challenge, err = base64.StdEncoding.DecodeString(challengeStr)
 			if err != nil {
-				uc.SendMessage(&irc.Message{
+				uc.SendMessage(ctx, &irc.Message{
 					Command: "AUTHENTICATE",
 					Params:  []string{"*"},
 				})
@@ -612,7 +612,7 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 			resp, err = uc.saslClient.Next(challenge)
 		}
 		if err != nil {
-			uc.SendMessage(&irc.Message{
+			uc.SendMessage(ctx, &irc.Message{
 				Command: "AUTHENTICATE",
 				Params:  []string{"*"},
 			})
@@ -625,7 +625,7 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 			respStr = base64.StdEncoding.EncodeToString(resp)
 		}
 
-		uc.SendMessage(&irc.Message{
+		uc.SendMessage(ctx, &irc.Message{
 			Command: "AUTHENTICATE",
 			Params:  []string{respStr},
 		})
@@ -669,7 +669,7 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 		}
 
 		if !uc.registered {
-			uc.SendMessage(&irc.Message{
+			uc.SendMessage(ctx, &irc.Message{
 				Command: "CAP",
 				Params:  []string{"END"},
 			})
@@ -707,7 +707,7 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 			}
 
 			for _, msg := range join(channels, keys) {
-				uc.SendMessage(msg)
+				uc.SendMessage(ctx, msg)
 			}
 		}
 	case irc.RPL_MYINFO:
@@ -931,7 +931,7 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 				})
 				uc.updateChannelAutoDetach(ch)
 
-				uc.SendMessage(&irc.Message{
+				uc.SendMessage(ctx, &irc.Message{
 					Command: "MODE",
 					Params:  []string{ch},
 				})
@@ -1531,7 +1531,7 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 			}
 			if found {
 				uc.logger.Printf("desired nick %q is now available", wantNick)
-				uc.SendMessage(&irc.Message{
+				uc.SendMessage(ctx, &irc.Message{
 					Command: "NICK",
 					Params:  []string{wantNick},
 				})
@@ -1711,7 +1711,7 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 			uc.nick = uc.nick + "_"
 			uc.nickCM = uc.network.casemap(uc.nick)
 			uc.logger.Printf("desired nick is not available, falling back to %q", uc.nick)
-			uc.SendMessage(&irc.Message{
+			uc.SendMessage(ctx, &irc.Message{
 				Command: "NICK",
 				Params:  []string{uc.nick},
 			})
@@ -1825,7 +1825,7 @@ func (uc *upstreamConn) requestCaps() {
 		return
 	}
 
-	uc.SendMessage(&irc.Message{
+	uc.SendMessage(context.TODO(), &irc.Message{
 		Command: "CAP",
 		Params:  []string{"REQ", strings.Join(requestCaps, " ")},
 	})
@@ -1882,7 +1882,7 @@ func (uc *upstreamConn) handleCapAck(name string, ok bool) error {
 			return fmt.Errorf("unsupported SASL mechanism %q", name)
 		}
 
-		uc.SendMessage(&irc.Message{
+		uc.SendMessage(context.TODO(), &irc.Message{
 			Command: "AUTHENTICATE",
 			Params:  []string{auth.Mechanism},
 		})
@@ -1902,28 +1902,30 @@ func splitSpace(s string) []string {
 }
 
 func (uc *upstreamConn) register() {
+	ctx := context.TODO()
+
 	uc.nick = GetNick(&uc.user.User, &uc.network.Network)
 	uc.nickCM = uc.network.casemap(uc.nick)
 	uc.username = GetUsername(&uc.user.User, &uc.network.Network)
 	uc.realname = GetRealname(&uc.user.User, &uc.network.Network)
 
-	uc.SendMessage(&irc.Message{
+	uc.SendMessage(ctx, &irc.Message{
 		Command: "CAP",
 		Params:  []string{"LS", "302"},
 	})
 
 	if uc.network.Pass != "" {
-		uc.SendMessage(&irc.Message{
+		uc.SendMessage(ctx, &irc.Message{
 			Command: "PASS",
 			Params:  []string{uc.network.Pass},
 		})
 	}
 
-	uc.SendMessage(&irc.Message{
+	uc.SendMessage(ctx, &irc.Message{
 		Command: "NICK",
 		Params:  []string{uc.nick},
 	})
-	uc.SendMessage(&irc.Message{
+	uc.SendMessage(ctx, &irc.Message{
 		Command: "USER",
 		Params:  []string{uc.username, "0", "*", uc.realname},
 	})
@@ -1960,7 +1962,7 @@ func (uc *upstreamConn) runUntilRegistered() error {
 		if err != nil {
 			uc.logger.Printf("failed to parse connect command %q: %v", command, err)
 		} else {
-			uc.SendMessage(m)
+			uc.SendMessage(context.TODO(), m)
 		}
 	}
 
@@ -1982,17 +1984,17 @@ func (uc *upstreamConn) readMessages(ch chan<- event) error {
 	return nil
 }
 
-func (uc *upstreamConn) SendMessage(msg *irc.Message) {
+func (uc *upstreamConn) SendMessage(ctx context.Context, msg *irc.Message) {
 	if !uc.caps["message-tags"] {
 		msg = msg.Copy()
 		msg.Tags = nil
 	}
 
 	uc.srv.metrics.upstreamOutMessagesTotal.Inc()
-	uc.conn.SendMessage(msg)
+	uc.conn.SendMessage(ctx, msg)
 }
 
-func (uc *upstreamConn) SendMessageLabeled(downstreamID uint64, msg *irc.Message) {
+func (uc *upstreamConn) SendMessageLabeled(ctx context.Context, downstreamID uint64, msg *irc.Message) {
 	if uc.caps["labeled-response"] {
 		if msg.Tags == nil {
 			msg.Tags = make(map[string]irc.TagValue)
@@ -2000,7 +2002,7 @@ func (uc *upstreamConn) SendMessageLabeled(downstreamID uint64, msg *irc.Message
 		msg.Tags["label"] = irc.TagValue(fmt.Sprintf("sd-%d-%d", downstreamID, uc.nextLabelID))
 		uc.nextLabelID++
 	}
-	uc.SendMessage(msg)
+	uc.SendMessage(ctx, msg)
 }
 
 // appendLog appends a message to the log file.
@@ -2073,6 +2075,8 @@ func (uc *upstreamConn) produce(target string, msg *irc.Message, origin *downstr
 }
 
 func (uc *upstreamConn) updateAway() {
+	ctx := context.TODO()
+
 	away := true
 	uc.forEachDownstream(func(*downstreamConn) {
 		away = false
@@ -2081,12 +2085,12 @@ func (uc *upstreamConn) updateAway() {
 		return
 	}
 	if away {
-		uc.SendMessage(&irc.Message{
+		uc.SendMessage(ctx, &irc.Message{
 			Command: "AWAY",
 			Params:  []string{"Auto away"},
 		})
 	} else {
-		uc.SendMessage(&irc.Message{
+		uc.SendMessage(ctx, &irc.Message{
 			Command: "AWAY",
 		})
 	}
@@ -2110,6 +2114,8 @@ func (uc *upstreamConn) updateMonitor() {
 		return
 	}
 
+	ctx := context.TODO()
+
 	add := make(map[string]struct{})
 	var addList []string
 	seen := make(map[string]struct{})
@@ -2148,7 +2154,7 @@ func (uc *upstreamConn) updateMonitor() {
 
 	if removeAll && len(addList) == 0 && len(removeList) > 0 {
 		// Optimization when the last MONITOR-aware downstream disconnects
-		uc.SendMessage(&irc.Message{
+		uc.SendMessage(ctx, &irc.Message{
 			Command: "MONITOR",
 			Params:  []string{"C"},
 		})
@@ -2156,7 +2162,7 @@ func (uc *upstreamConn) updateMonitor() {
 		msgs := generateMonitor("-", removeList)
 		msgs = append(msgs, generateMonitor("+", addList)...)
 		for _, msg := range msgs {
-			uc.SendMessage(msg)
+			uc.SendMessage(ctx, msg)
 		}
 	}