"Many companies are hesitant to offer a trial extension, but the cost of doing so in most cases seems absolutely trivial." I totally agree with you that this i

"Many companies are hesitant to offer a trial extension, but the cost of doing so in most cases seems absolutely trivial." I totally agree with you that this is crazy. Not only is the cost trivial, but you've potentially spent a ton of money to get them using your app! Recovering this sale is unspeakably cheaper than acquiring a totally new customer. The counterpoint could be that by asking for a trial extension, they've clearly signaled that they value the product. Perhaps with a nudge they will get out their credit cards. But if the app is doing its job, they'll be more engaged at the end of 2 months, so it should be an easier sale and one month's revenue will come out in the wash. This seems to match UserVoice's experience, where conversions from this group were 2.5x higher.