Over the last few years I have used a few different services, I have noticed that most of the ones that offer month-to-month billing have a flaw in their systems that they have no desire to fix. The subscription-based services which auto-bill you every month for the most part don't have this problem, but I'm not one to trust a company until I have some experience with them, so I always start month-to-month on these services.
Let's say that I pay on 1/1 for a full month, which gives me a period of service from 1/1 to 2/1. But on 1/20 the service starts spamming my email, informing me that my month is about to expire. So I pay the service on 1/20 and think everything is fine and I'm good until 3/1, right? Wrong. Now on 2/10 I'm getting those spam emails, telling me my service is about to expire on 2/20. Where did those 10 days go?
The answer is they took those 10 days of service from you. If you call or email to complain, chances are they will credit your account those 10 days. But they won't fix the problem, and next month you'll be in the same boat. What's worse, if you don't say anything or don't notice it, they will happily keep shorting you service. Once company refused to credit me the difference so I was forced to file a PayPal claim.
I can hear someone saying "just let it expire before you pay it again" but nope, most of these services charge you a late fee if you let it expire first.
1. Use a subscription-based VPN service that auto-bills you every month and keep an eye on them.
2. Use a VPN service that doesn't charge you a late fee if you let your service expire.
3. Use a VPN service that lets you pay in advance but defer the activation until after it expires.
I've been writing this type of computer billing code for insurance companies for decades, and it's not rocket science. The logic to bill and adjust for money by date is very straightforward. No, the real reason these companies do it is because they can. They assume right off the bat that you are doing something shady by using their service, so you will not complain too loudly. So they have no incentive or reason to fix the problem, which probably makes them a lot of money.
For this article I will not shame the bad services I have run across, because they almost seem to be universally bad. What I will say is that my current VPN service BolehVPN allows me to wait until my service expires to re-up with another payment. They also let you defer the activation of your payment for up to 60 days, so I can pay for it when it expires, and then just activate the next billing period when I'm ready.
There are a whole lot of folks out there who have a personal or profitable interest in shaming you into believing that you are not worthy of privacy. You must be hiding something, right? We're all hiding something. I doubt anyone has their banking site passwords taped to their front door. You deserve privacy, and the folks who have a vested interest in profiting from it or taking it away will do everything they can to make you feel like a second class citizen.
The answer is to hold these shady companies accountable for screwing you over 10 days of service at a time. You are not a second class citizen. Treat them how you would treat your phone or cable company and don't cut them any slack for assuming you are too ashamed to ask for your money back!