Troublesome/ˈtrʌblsəm/ Definition 1 of 3Pro Tip 1/3Negative Connotation Troublesome usually implies a negative impact on others or situations. Their troublesome arguments often left the team frustrated. Pro Tip 2/3Persistent Problems Troublesome suggests ongoing problems, not just one-time events. The software bugs were particularly troublesome for the users. Pro Tip 3/3Manageable Challenges Despite being difficult, troublesome things can often be managed with effort. Organizing the event was troublesome, but it turned out great.