Did I screw up by purchasing the $29.00 Black Friday special when my account doesn't expire until March 2026?

I’ve been a subscriber since 2018, using vouchers all the time. Each voucher simply extended my expiry date - which until yesterday was March 2026. I saw the Black Friday special, purchased it, and my expiry date moved a year ahead to March 2027. So far so good – but since I bought a yearly plan, does this mean I will be charged again in November 2025 for another year of service – further extending my expiry date to March 2028? In other words, have I now committed to pre-paying for my service by about 2 years and 4 months?

Yes, you will be. I am facing similar issue now. My original plan was via vouchers and it was all good. Until late last year I purchased the ‘cheapest ever plan’ thinking I can extend my expiry which it did. But alas, I was charged for recurring fees after 1 yr not because of ny expiry ran out (e.g. my plan expires in 2027) but because I was charged due to my ‘cheapest ever plan’ is due. I thought the last plan I had purchased will append to my existing plan using vouchers but not the case. This is just absurd.

Support wasn’t entirely helpful at all. They simply asked me if I want to cancel my ‘cheapest ever plan’. I guess their billing system is just ‘state-of-the-art’.

As I have been with Windscribe since 2017, I initially had the free plan and was able to score the lifetime 50 gb free plan and soon after came the vouchers so I got a discounted 3-year plan, twice. Now it expired and I am back to my previous 50 gb free plan. Waiting for a new 3-year promo, until then I will slow down my VPN (over)usage.

Pro Tip: never extend a subscription before it expires. Some companies will beg you to extend and they will offer discounts.

You will be charged next year on November 2025, and if you don’t pay, you will keep your Pro status until expire date but then lose all the discounts. I know, great logic from billing team.

I don’t fuck with deals. I bought a year from Google Play, so it’s set to renew every year. It’ll take money whether my account is expiring or not. I bought a deal plan once, extended my expiry and Google Play still takes yearly payments. So essentially I bought a plan I can’t use.

i did subscribe-cancel-subscribe 3 times. then i asked ai support bot and had been told that next charge would be in 2028.

here flexing my 10 bucks per year deal

I got a deal for being og member 10 dollar a year

I’m also facing this issue, their solution was for me to cancel my plan. My solution is that they should refund to cost of the plan for each year I pre-purchased. Honestly, I would be ok with a compromise, because I want to lock in the yearly cost instead of continually waiting for voucher deals.

Thanks for the info. I was naive to think that my renewal of the my version of “cheapest plan ever” would begin at the end of my current expiry date. I suppose I could cancel before the renewal period and wait for future voucher deals closer to March 2028. Really wish I had jumped on the lifetime deals when they first started up. Overall I’m happy with the service, so I plan to stick around. End of the day, I have nearly a year to decide – it just seems so absurd to have to play these games of subscription roulette.

Did it add another year to your expiry or did it just charge you and your plan didn’t extend?

I had this exact same dilemma too with the Cheapest Almost Ever promo. I thought it would stack on top of my already existing recurring plan, but that wasn’t the case. I was still billed $19 this year, despite my expiry date being in 2026.

The main issue for me is that there are two different tiers of Windscribe users: those who use vouchers, and those who subscribe to monthly/yearly plans. It causes confusion because the vouchers usually say that they are only for new users – when in fact, previous voucher users can actually use new vouchers. Monthly/yearly subscribers, however, can not take advantage of voucher deals unless they actually cancel their subscriptions. That’s my understanding, and if it’s correct, it’s a very confusing model, particularly to new users of the service.

So is liked some marketing gimmick to entice users to subscribe without providing any disclaimer?

How long after the expiration date did you receive it?

Don’t think thats being naive. One would think that by adding onto an active plan, it would append to it. But no, Windscribe chooses to add this newly subscription ahead of your current plan. Really dunno what they were thinking.

Windscribe didnt manage to deduct any monies from me. It is still pending for me to pay my subscription. I suppose it will just extend (not append) which doesn’t make sense as I still have about 2-3yrs left from my previous plan claimed thro’ a voucher. Then I will never utilize this remaining plan if I continue to extend.

It added another year to the expiry date – which is what I expected it to do. So that was fine. I just hoped the renewal wouldn’t kick in until the revised expiry date had been reached.

Good point. I initially used vouchers twice before I actually paid directly for a 3-year plan for $69. I even forgot about the vouchers and now I am waiting for the promo email. Last time it came 2 weeks after my 3-year voucher plan expired.

Exactly my case. I buy recurring yearly plans, and the only way to use vouchers is to cancel my plan. It sucks seeing all these deals people are jumping on, but I can’t without canceling, and I’m 99.9% sure some issue will arise if I try. I’ll get banned for making new accounts or something.