1

The user is on a free trial. When user goes to account settings, there's a button that allows to "buy subscription". When a subscription is bought and user want's to change a plan the same button says "upgrade account".

Is that distinction ok? Or should the button say "upgrade account" in both situations?

But as I think about it user can downgrade account as well to a cheaper subscription, so it woun't be fair to name the button "upgrade account".

Maybe "change subscription"?

4

When the user is not already a subscriber go with something like:

mockup

download bmml source – Wireframes created with Balsamiq Mockups

Do you really need to use the button label to communicate that subscriptions are something you "Buy" or "Purchase"? I imagine this is something that will become clear as soon as they initiate the process, and as John Gladding's answer suggests, even though the user knows they're going to have to pay for something at some point, it's arguably more sensible to restrict language that overtly reminds them of this fact up front. The verb 'Subscribe' should be perfectly sufficient to communicate the function.

When the user is already a subscriber, go with:

mockup

download bmml source

Some might argue that 'Manage' is weak verb for a Call To Action, but in your case, where it's linking to multiple actions like upgrading, downgrading, and cancelling, it's quite appropriate.

2

"Buy" implies "part with your money". There is a reason Amazon asks you to put in your credit card info at the end of a transaction - studies have shown that if you put it at the beginning, there is a higher drop-off rate. In other words, don't stick your hands out for money.

"Upgrade" isn't as obvious as "give us money". Some may argue it's simply semantics. However I would bet your bottom dollar that if you did a live A/B test with real money, the "Upgrade" option would end up with more transactions.

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