When is it appropriate to use emoticons to convey tone, and when should they be used sparingly? 

When communicating with individuals familiar with and comfortable using emoticons, using them appropriately can enhance the communication experience. 

Emoticons should be used primarily in serious or sensitive conversations to soften the impact of the message and provide comfort. 

Emoticons should be used sparingly when communicating with close friends or family, as they may already understand the intended tone without their use. 

Emoticons should be used sparingly in all types of communication as they can be perceived as unprofessional or childish. 

Additionally, emoticons should be used discreetly in professional settings such as work emails or formal business communication. Using them too frequently may detract from the professionalism of the message. 

Emoticons should also be used sparingly when communicating with individuals who are not familiar with or comfortable with their use. They may find them confusing or unprofessional, so it is best to err on the side of caution. 

Ultimately, the appropriateness of using emoticons to convey tone depends on the context, the relationship with the recipient, and the purpose of the communication.