Have you successfully raised prices?

I started OnlineOrNot at $9/mo, it's now $14/mo for the cheapest plan (with a few experiments along the way).

You can raise prices at any time without backlash, as long as current users continue to get the deal they signed up for. Just change it for new users.

The issue is then, if you raise prices too far, and fewer folks start signing up. You may want to lower prices, and update folks on the higher price to have the cheaper price (to avoid backlash).

We raised fees on a payments product this year, gave a few months notice, gave solid rationale, and saw little to no churn or complaints. I think it all comes down to value though, if your users value your product and think of you in a positive light you should be fine. Ours is still very cheap compared to the benefits and would be a minor expense for customers.

With recurring billing you may see some users churn who "forgot" about the charge in the first place and were likely not using the product.

FWIW This past year ive been stung so much by SAAS price hikes its fundamentally changed my internal equation of "when to SAAS VS when to self-host/build". Messaging apps have been the worst offenders, adding new features that we don't use and using this as an excuse to up prices to ridiculous levels. Overall positive perhaps, now using more self-hosted OS software.

If you increase services then increase prices, users are often fine with it. What sucks is when something gradually reduces services, then cuts headcount, then asks for more money. That's when everyone finds alternatives.