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I have a few WordPress plugins (I won't list them to avoid advertising). One of these plugins has over 20k active installations. Generally speaking, at what point should a plugin have enough users to justify investing time in developing a pro version?

> Generally speaking, at what point should a plugin have enough users to justify investing time in developing a pro version?
A pro version is about added business value, not about number of installations.
If it adds business value -> add a price to it so people can make money by installing your plugin, and you earn on them making money.
If it doesn’t add business value -> figure out what value it does cover (if any) and how much that’s worth to your users. But this’ll be tougher because it’ll be about personal values instead of business value.
When people ask you for more features **repeatedly**.
I’m in the same exact situation. Mine’s at 30K+. But I really don’t want to do what Yoast did when Joost de Valk sold his business to a private equity company, and start pestering my users to buy something.
As an user, if a free plugin suddenly decided to become paid, with no added value whatsoever (actual value, not bullshit marketing) I’d drop it immediately and seek alternatives.
What features to be paid and which free, that’s for you to decide based the plugin, user’s behaviour, etc. Mostly try to leave anything massively used (4-50%) free so it has outreach, then any upgraded version of that or extras, paid.
Keep free plugin free and maintain it, so you don’t lose existing users. Create pro version – add extra flexibility/options in pro version that saves even more time for devs; Monetise yearly support. Alternatively keep dope free plugin, manage donations from sponsors to maintain plugin for free. Do marketing to attract more users. Strategise plugin future and exit options to sell your plugin if you no longer want/able to work on it.