Every point of contact is critical and has the basic potential to either make or break a relationship. Therefore, carefully consider the moment (via which channel, with what “tone of voice,” automated or not) when addressing someone.
The context is always leading, and relevance is essential. Both in terms of content and timing, as well as the choice of channel and associated quality requirements. You can be as relevant as possible, your timing perfect, but if the connection drops during a conversation, it can have disastrous consequences.