It's a one-time purchase where you automatically get the upgrades. If you aren't getting the upgrades, there might be something amiss with your Pleco account (purchases not synched with your ID, etc)I don't understand the pricing of the Outlier dictionary. I seem to have Expert and Essentials. The latest upgrade to Essentials would cost me $19.99. Is that correct? Just asking. I had assumed that buying the dictionary would include the upgrade. Not complaining, I just don't find it clear.