ConnectWise vs Autotask vs HaloPSA: Picking the Right PSA for Your MSP

If you're evaluating PSA platforms right now, you're probably looking at three names: ConnectWise PSA, Datto Autotask, and HaloPSA. There are others — Syncro, Halo ITSM, Freshdesk, ServiceNow — but for dedicated MSP operations, these three own the conversation.

I work on ConnectWise and HaloPSA regularly, and I've migrated enough MSPs away from Autotask to have strong opinions about all three. What follows is my honest assessment of each platform's strengths, weaknesses, and ideal fit.

ConnectWise PSA

Best for: Established MSPs with 15+ techs, complex billing structures, and an existing ConnectWise ecosystem investment.

ConnectWise is the incumbent. It's been the default PSA for mid-to-large MSPs for over a decade, and that install base comes with a massive ecosystem advantage. Every vendor in the MSP space integrates with ConnectWise. Every consultant has touched it. Every peer group has members running it.

The platform itself is deep. There are very few MSP operational scenarios that ConnectWise can't handle. Agreement billing supports exotic structures. Workflow rules are powerful. The API covers most of what you need. Reporting, while clunky natively, has excellent third-party options through BrightGauge and Power BI.

The downsides are well-documented by the community at this point. The interface feels dated. The pricing is aggressive and getting more so — multi-year contracts, annual increases, and a bundling strategy that makes the true cost hard to pin down until you're deep into a sales conversation. The pace of innovation is slow. Bug fixes take months. Feature requests take years.

And the ownership situation matters. ConnectWise is PE-backed, and the decisions that come with that ownership model — prioritizing margin over product investment, pricing power over customer satisfaction — are visible in the community sentiment.

If you're already on ConnectWise and it's configured well, the switching cost is high and the grass isn't always greener. If you're evaluating it for the first time, the price and contract terms may give you pause.

Datto Autotask

Best for: MSPs that want tight RMM integration out of the box and prefer a more streamlined (less customizable) approach.

Autotask's defining characteristic is its integration with Datto RMM. If you're running the Datto ecosystem — Datto RMM, Datto BCDR, IT Glue — Autotask fits neatly into that stack with minimal integration friction. The combined Datto ecosystem experience is genuinely smooth when it works.

The platform is simpler than ConnectWise. That's both a strength and a limitation. It's easier to learn, faster to implement, and less likely to suffer from the configuration drift that plagues ConnectWise environments. But "simpler" also means "less flexible" — when you need a complex billing arrangement, an unusual workflow, or a custom integration with a niche tool, Autotask may not accommodate it without workarounds.

The reporting has improved but still trails ConnectWise and HaloPSA for depth and customization. The API is functional but not as developer-friendly as HaloPSA's.

The concern with Autotask is the same as ConnectWise: Kaseya ownership. Kaseya's acquisition of Datto brought the same PE-driven pricing and contract dynamics that ConnectWise shops are dealing with. Community sentiment around Kaseya's management of the Datto product line has been mixed at best.

If you're deeply invested in the Datto ecosystem and value the out-of-box integration experience, Autotask makes sense. If you're not locked into Datto, the value proposition is less clear.

HaloPSA

Best for: MSPs under 500 endpoints implementing their first PSA, MSPs migrating away from ConnectWise or Autotask, and MSPs that value modern tooling and vendor responsiveness over ecosystem breadth.

HaloPSA is the growth story. Year-over-year growth numbers that dwarf the incumbents, a development team that ships features at a pace ConnectWise and Autotask can't match, and pricing that undercuts both established players significantly.

The interface is modern and intuitive. The API is excellent. The billing system handles what most MSPs need (though it's less mature than ConnectWise for exotic billing arrangements). The client portal is solid. The automation engine is capable and getting more capable with every release.

The weaknesses are the weaknesses of any newer platform: the integration ecosystem isn't as broad as ConnectWise's (though it's growing fast), some advanced features are still maturing, and the partner/consultant ecosystem is smaller — which means finding help with implementation or optimization isn't as easy as it is in the ConnectWise world.

HaloPSA's trajectory matters as much as its current state. The platform today is meaningfully better than it was a year ago, and it'll be meaningfully better a year from now. ConnectWise today is... roughly the same as it was a year ago, and the year before that.

How to actually decide

Forget the feature comparison matrices. Every PSA vendor's marketing site shows a grid where their product has checkmarks everywhere and the competitors have gaps. Those grids are designed to sell, not to inform.

Instead, evaluate based on these factors:

What's your current ecosystem? If you're deeply embedded in ConnectWise or Datto tooling, switching PSAs means switching multiple tools. Factor in the total migration cost, not just the PSA license.

What's your team size and complexity? A 5-person MSP with straightforward billing doesn't need ConnectWise's depth. A 50-person MSP with complex agreement structures, multiple service tiers, and dozens of integrations needs a platform that can handle that complexity.

What's your budget sensitivity? If ConnectWise's pricing is straining your margins, that's a legitimate reason to evaluate alternatives. If pricing isn't a significant concern, it's one less reason to switch.

How important is vendor trajectory? If you're making a 5-year platform decision, the vendor's development velocity, pricing trajectory, and ownership structure matter. A platform that's getting better every quarter is a different bet than one that's stagnating.

Do a real pilot. Don't pick a PSA based on a demo. Get a trial environment. Configure your actual service boards, create real test tickets, build a sample agreement, and have two or three team members use it for actual work for a week. The friction points you discover in a real pilot are worth more than any amount of feature comparison.

The option nobody talks about: optimize what you have

If you're evaluating new PSAs because your current one frustrates you, it's worth asking whether the frustration is with the platform or with your configuration of the platform.

I've talked several MSPs out of migrations after discovering that the issues driving their frustration — slow workflows, inaccurate billing, useless reporting — were configuration problems, not platform limitations. A $5,000–$10,000 optimization engagement solved problems they thought required a $30,000+ migration.

That's not always the case. Some MSPs genuinely need a different platform. But make sure you're solving the right problem before you commit to the cost and disruption of a switch.

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Trying to decide? Book a discovery call and I'll help you evaluate based on your actual setup, not marketing materials.