diff --git a/pkg/services/telegram_agent_service.go b/pkg/services/telegram_agent_service.go
index c82d793..18501a5 100644
--- a/pkg/services/telegram_agent_service.go
+++ b/pkg/services/telegram_agent_service.go
@@ -1031,10 +1031,26 @@ Comandos: /reset /instancias /ayuda`, nil
 		{Role: "system", Content: agentSystemPrompt()},
 	}
 	for _, h := range history {
-		msg := agentMessage{Role: h.Role, Content: h.Content}
-		if h.Role == "tool" {
+		msg := agentMessage{Role: h.Role}
+		switch h.Role {
+		case "tool":
+			// Restaurar tool result: ToolCallID viene de ToolName (donde guardamos tc.ID)
 			msg.ToolCallID = h.ToolName
 			msg.Content = h.ToolResult
+		case "assistant":
+			// Si el Content es un array JSON, son tool_calls serializados — restaurarlos
+			content := strings.TrimSpace(h.Content)
+			if len(content) > 0 && content[0] == '[' {
+				var tcs []agentToolCall
+				if json.Unmarshal([]byte(content), &tcs) == nil && len(tcs) > 0 {
+					msg.ToolCalls = tcs
+					// Content debe quedar vacío cuando hay tool_calls (Anthropic lo requiere)
+					break
+				}
+			}
+			msg.Content = h.Content
+		default:
+			msg.Content = h.Content
 		}
 		messages = append(messages, msg)
 	}