This is a dark pattern usually dying companies like to follow. Why? Because, if you are confident of the value you provide to your customer, you don't need to be so aggressive about not letting them go. Yes, retention is an important KPI, but trust and transparency are even more important than anything else, so companies that offer little value and can't keep up with competition usually do this because they know they are dying.

A little while ago, I noticed the dark pattern that dropbox uses and showed it to my friend while talking about dark patterns. Turns out he was in charge of his university for selecting a good vendor for file storage. He saw it and immediately said 'fuck that' and went for another vendor instead. You see, this is how dark patterns shoot you in the foot - the cost of trust and transparency is even higher. In this case, dropbox lost significant money that they could have otherwise won.

Besides, In this day and age, there is literally no value that dropbox offers to its users. Their competitors offer way more value for similar price points and the experience with dropbox isn't even that good. All they have is their brand name, which will also be gone soon after they've tortured their customers with these dark patterns.