The MSP tooling market turned into a bloodbath in 2025. Kaseya bundled everything into Kaseya 365 at a price designed to make ConnectWise partners think twice about renewing. ConnectWise hit back with AI-powered PSA and an M365 security suite built with Microsoft and Pax8. Pax8 kept expanding their marketplace and playing Switzerland.
I’ve spent time in all three over the past few months. Here’s where I landed. Kaseya 365 wins on price, no question. ConnectWise wins on ecosystem depth, the integrations are just more mature. Pax8 wins on flexibility, you’re not locked into their stack the way you are with the other two. If you want to know what’s actually real in PSA and RMM AI features, I tested those too.
There’s no wrong answer. But there is a wrong strategy, and it’s running pieces of all three because you can’t make a decision. The MSP bifurcation playing out in 2026 is partly about this — the providers pulling ahead are the ones who picked a platform and went deep. The open ecosystem wars mean every platform has gravity — pick the one you can live with. Pick your stack. Go deep. Learn the automations. Build the workflows. The MSPs winning right now aren’t the ones with the most tools. They’re the ones who know their tools cold. And if you’re still figuring out the build vs. buy vs. wait decision on AI in your PSA, that choice matters just as much as which platform you pick.