> I'm a little confused on how you are interpreting the majority of your customers opting for discounted pricing as an indication that you should raise prices.

The way I see it, most customers are happy enough after a 30-day trial to commit to my product for at least a full year. That's a good signal for loyalty and the product being worth it for the price. While I agree that the discount aspect is a signal in the other direction, I think overall it looks like people will continue to subscribe even if it's pricier. That's why I'm leaning towards increasing prices. I don't know much about businessy things and I'm learning as I go, so take my opinions with a grain of salt.

I've had some really good suggestions in this thread to talk to my most recent subscribers to really understand why they paid annually straight off the bat, so I'm going to do that first before taking any action.