This study aimed to develop a help system for a communication app, identify usability issues regarding that help system and develop redesigns to improve it. The focus was to maximize perceived usefulness and minimize perceived annoyance of the help system. During the study two design proposals were developed and two user tests, which used low-fidelity prototypes. were performed to evaluate the design proposals. The first design proposal was evaluated in the first user test, thereafter an iteration of that design was developed based on the usability issues found in the user test. This iteration of the design was the second design proposal which were evaluated in the second user tests. Both design proposals and data from both user tests were analysed to- gether which resulted in seven recommendation that aimed to maximize perceived usefulness and minimize perceived annoyance when developing a help system for a communication app. Due to a lack of generalizability these recommendations should however be used with caution since they are mainly applicable to the system evaluated in this study. They can however be used as an inspi- ration and a starting point for someone designing a help system for an other communication app.