diff --git a/assistant.go b/assistant.go
index 4e05fe0..3e115b0 100644
--- a/assistant.go
+++ b/assistant.go
@@ -93,9 +93,19 @@ func assistantStreamedResponse(request openai.ChatRequest, cb assistantStreamedR
 	logger.Debugw("Openai chat request", "req", request)
 	ai := openai.NewClient(config.OpenAIApiKey)
 
-	resp, err := ai.ChatCompletionStream(request)
-	if err != nil {
-		return err
+	var (
+		resp *openai.ChatResponseStream
+		err  error
+	)
+	tries := 2
+	for {
+		if tries--; tries < 0 {
+			return err
+		}
+		if resp, err = ai.ChatCompletionStream(request); err == nil {
+			break
+		}
+		logger.Warnw("assistant: failed to get response", "error", err)
 	}
 
 	nErrs := 0
@@ -242,8 +252,9 @@ func handleAssistantConversation(c tele.Context, thread []*tele.Message) error {
 
 	if reqErr != nil {
 		logger.Errorw("assistant: failed to complete conversation", "error", reqErr)
+		return c.Reply("Sorry, there's a technical issue. 😵💫 Please try again later.", tele.Silent)
 	}
-	return reqErr
+	return nil
 }
 
 func assistantRemoveMention(msg, name string) string {