First, take a deep breath and remember the rule of internet. If something is available for free, people WILL find it, use it and abuse it. Don't beat yourself t

First, take a deep breath and remember the rule of internet. If something is available for free, people WILL find it, use it and abuse it. Don't beat yourself too much for it. "I'm reluctant to jump in and accuse them of abusing the free trial" No, don't be reluctant. Reach out to them with a kind email saying that their trial period has expired and they need to switch to a paid account. Alternatively, offer them an extended trial period using same account if you think they may give you business BUT do not let them abuse the trial system. Here is how I will do it: "Hi xyz. We noticed that you created a trial account using username abc for your company. We wanted to reach out and ask if someone from your company has created another trial account after the expiry of the first one (This way, you are not directly accusing but smartly letting them know). We are happy to give you an extension of trial period if you need but as per our terms and conditions, you are not allowed to create multiple trial accounts for same company. If you have any questions on this, I will be happy to assist" Another way to think about this. Perhaps this client needs more time to evaluate the product and hence give them the benefit of the doubt at first. They continue to use the product actively which means they definitely like something about it. This could be good news for you. Take this opportunity to reach out to them and have a conversation. You never know what will happen.