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Yes, we do pro-rate all upgrades. "Pro-rating" means that we will apply any remaining funds you have on your current account towards the purchase of additional space.
For example, if you have a 1 TB annual plan that was purchased four months prior, you have paid $10.75 per month (129/12=$10.75) or $43 in total ($10.75x4=$43). If you then decide to upgrade to a 5 TB annual plan, we will now calculate how much money you have unused on your current account and credit it towards your new purchase. In this example, you have used $43 which means you have $86 remaining in credit ($129-$43=$86).
We now subtract your credit from your purchase of the 5 TB annual plan. The $279 minus your remaining credit of $86 is $193, which is what you will be billed to upgrade this account.