At what point does custom software become worth the investment?

I've noticed that many businesses start with off-the-shelf software because it's faster and less expensive to implement.

But over time, as workflows become more complex, integrations are needed, and operational requirements grow, some companies start considering custom solutions instead.

I was researching different approaches recently, while looking into healthcare-focused software projects. It got me thinking about where the tipping point actually is.

For business owners who have made the switch, what was the moment you realized your existing software was holding you back? Did the move to a custom solution end up paying off?