diff --git a/agent/agent.go b/agent/agent.go
index 863af7b59fbbb..52c423787fb44 100644
--- a/agent/agent.go
+++ b/agent/agent.go
@@ -236,7 +236,9 @@ func (a *agent) runLoop(ctx context.Context) {
 		if err == nil {
 			continue
 		}
-		if errors.Is(err, context.Canceled) {
+		if ctx.Err() != nil {
+			// Context canceled errors may come from websocket pings, so we
+			// don't want to use `errors.Is(err, context.Canceled)` here.
 			return
 		}
 		if a.isClosed() {
diff --git a/codersdk/agentsdk/agentsdk.go b/codersdk/agentsdk/agentsdk.go
index 7f66c01bc864b..e2189e1cc53d2 100644
--- a/codersdk/agentsdk/agentsdk.go
+++ b/codersdk/agentsdk/agentsdk.go
@@ -204,7 +204,7 @@ func (c *Client) DERPMapUpdates(ctx context.Context) (<-chan DERPMapUpdate, io.C
 		defer close(updates)
 		defer close(updatesClosed)
 		defer cancelFunc()
-		defer conn.Close(websocket.StatusGoingAway, "Listen closed")
+		defer conn.Close(websocket.StatusGoingAway, "DERPMapUpdates closed")
 		for {
 			var update DERPMapUpdate
 			err := dec.Decode(&update.DERPMap)
@@ -240,7 +240,7 @@ func (c *Client) DERPMapUpdates(ctx context.Context) (<-chan DERPMapUpdate, io.C
 		closeFunc: func() error {
 			cancelFunc()
 			<-pingClosed
-			_ = conn.Close(websocket.StatusGoingAway, "Listen closed")
+			_ = conn.Close(websocket.StatusGoingAway, "DERPMapUpdates closed")
 			<-updatesClosed
 			return nil
 		},