HaloPSA vs ConnectWise: An Honest Comparison From Someone Who Works on Both

I work on both ConnectWise and HaloPSA regularly. I configure them, optimize them, migrate data between them, and troubleshoot them when something goes sideways. I don't have a financial incentive to push one over the other, and I'm not a partner reseller collecting referral fees. So what follows is as close to an unbiased comparison as you'll find from someone with hands-on experience in both platforms.

Fair warning: neither platform is objectively "better." What's better depends on your MSP's size, complexity, budget, technical appetite, and existing integrations. I'll try to lay all of that out honestly.

The big picture difference

ConnectWise is a mature, enterprise-grade platform with an enormous ecosystem. It does a lot, it integrates with everything, and it's been the default PSA for mid-to-large MSPs for over a decade. It's also complex, expensive, slow to modernize, and owned by a private equity firm whose pricing decisions have frustrated a lot of people.

HaloPSA is the newer challenger that's been growing fast — really fast. Modern interface, aggressive pricing, rapid feature development, and a genuinely good API. It's not as deep as ConnectWise in some areas yet, but it's closing the gap quickly, and for many MSPs it already does everything they actually need.

The interface

I'm going to be blunt: ConnectWise's interface feels old. It's functional. You can get things done. But it's a dense, Windows-style UI that takes significant time to learn, and even experienced users find themselves clicking through four or five menus to reach something that should be two clicks away. The pod system is powerful once you learn it, but the learning curve is steep and there are very few quality-of-life touches.

HaloPSA's interface is modern. It feels like software that was designed in the last five years, because it was. The navigation is more intuitive, the layout is cleaner, and the ticket experience is noticeably better for technicians — which matters, because your techs live in the PSA eight hours a day. That said, "modern UI" doesn't automatically mean "easy." HaloPSA has its own complexity, especially around module configuration, and the admin panel has a learning curve of its own.

If your team already knows ConnectWise, switching to HaloPSA just for a nicer interface is probably not worth the migration cost. But if you're implementing from scratch or your team actively hates using ConnectWise, the UX difference is meaningful.

Pricing

This is where things get spicy.

ConnectWise pricing has been a sore point in the MSP community for years. Mandatory multi-year contracts, aggressive annual increases, and a pricing structure that penalizes smaller MSPs. I've talked to shop owners paying over $150 per user per month when you factor in the ConnectWise ecosystem costs — PSA, RMM, BrightGauge, ITBoost, and whatever else they've been bundled into.

HaloPSA prices per agent and it's meaningfully cheaper. Most MSPs I've talked to see 30–50% savings on the PSA license alone when they switch. HaloPSA also doesn't lock you into long-term contracts the same way, and their pricing has been more predictable.

But — and this is a big but — the license cost is only part of the equation. The cost of migrating, the productivity hit during transition, the integrations you need to rebuild, the training time, and the consulting hours to configure everything properly can add up fast. I've seen migrations where the first-year total cost (license savings minus migration investment) was roughly a wash, and the real savings didn't materialize until year two.

Run the numbers with your actual data, not with best-case assumptions.

The API

HaloPSA's API is genuinely excellent. It's well-documented, RESTful, covers most of the platform's functionality, and is pleasant to work with as a developer. I can build integrations against HaloPSA significantly faster than I can against ConnectWise.

ConnectWise's API is functional but shows its age. The documentation is decent for the REST API (the older SOAP API should be avoided if possible), and it covers a wide range of endpoints. But there are quirks, inconsistencies, and some areas where you have to work around limitations that shouldn't exist in 2026.

For MSPs that rely heavily on custom integrations or use a platform like Rewst for automation, the API quality matters. HaloPSA has an edge here.

One thing worth noting: ConnectWise made some changes to their terms of service a while back that restrict using their API to export data to competing platforms. This has created real headaches for MSPs trying to migrate away. HaloPSA doesn't have similar restrictions, which is worth considering if platform flexibility matters to you.

Integrations ecosystem

This is ConnectWise's strongest advantage, and it's significant.

ConnectWise has been the market leader for over a decade, which means virtually every tool in the MSP ecosystem has a ConnectWise integration. RMMs, documentation platforms, security tools, backup vendors, accounting software, VoIP providers, quoting tools — if it's an MSP product, it almost certainly integrates with ConnectWise.

HaloPSA's integration ecosystem is growing quickly but it's not at ConnectWise's level yet. The major integrations are there — Microsoft 365, Azure, common RMMs, QuickBooks, Xero — but you're more likely to hit a gap with a niche vendor tool. When that happens, you're building a custom integration via the API or using middleware like Rewst or Power Automate to bridge the gap.

If your tech stack includes a lot of specialized tools with ConnectWise-specific integrations, migrating to HaloPSA means auditing every single one of those integrations to confirm there's an equivalent. Some will have native HaloPSA support. Some won't. Plan accordingly.

Billing and agreements

ConnectWise's agreement and billing system is incredibly powerful once it's configured correctly. Multiple agreement types, complex addition structures, prepaid hours, block time, overages — it handles sophisticated billing arrangements that larger MSPs need. The downside is that this power comes with complexity. Misconfigured agreements are probably the single biggest source of revenue leakage I see in ConnectWise environments.

HaloPSA's billing is simpler and, for most MSPs, sufficient. It handles recurring contracts, per-user/per-device billing, and integrates with accounting platforms cleanly. Where it's less mature is in some of the edge-case billing scenarios — complex overage calculations, multi-tier agreement structures, and some of the granular billing automation that ConnectWise supports out of the box.

For MSPs under 500 endpoints with relatively straightforward billing, HaloPSA's billing is plenty. For larger MSPs with complex agreement structures across multiple client tiers, ConnectWise's billing depth still has an edge — assuming it's actually configured to use that depth, which is a big assumption.

Reporting

ConnectWise's built-in reporting (Report Writer) is functional but widely disliked. It works, but building a custom report feels like it takes three times longer than it should. Most ConnectWise shops end up using BrightGauge or Power BI for anything beyond basic canned reports.

HaloPSA's reporting through NHServer is solid and improving. It's more modern than ConnectWise's native reporting, and HaloPSA has been investing in their reporting capabilities. That said, for advanced analytics, most MSPs on either platform end up using a third-party BI tool anyway.

I'd call reporting roughly even with a slight edge to HaloPSA for out-of-the-box usability, and a slight edge to ConnectWise for ecosystem options (BrightGauge is mature and well-integrated).

Feature development and responsiveness

This is where HaloPSA shines and ConnectWise frustrates people.

HaloPSA ships updates regularly — sometimes weekly. Their development team is responsive to feature requests, and MSPs who've interacted with their team consistently praise the pace of iteration. Features that get requested in community forums sometimes appear within months.

ConnectWise moves slowly. Major features take years. Bug fixes take months. The MSP community has been vocal about the gap between what ConnectWise promises at IT Nation and what actually ships. Some of this is the natural inertia of a mature platform with a massive codebase, and some of it is the reality of PE ownership where R&D investment takes a back seat to margin optimization.

If you care about platform trajectory — where will this tool be in three years? — HaloPSA's momentum is hard to ignore.

My honest take: who should use which?

ConnectWise makes sense if:

• You're already running it and it's configured well
• You have complex billing with multi-tier agreements and sophisticated overage rules
• Your tech stack is deeply integrated with the ConnectWise ecosystem
• You're over 500 managed endpoints and need enterprise-grade depth
• Your team is trained on it and productive

HaloPSA makes sense if:

• You're implementing a PSA for the first time
• You're a smaller MSP (under 500 endpoints) looking for modern tooling at a lower price point
• You're frustrated enough with ConnectWise's pricing, contracts, or pace of development to justify a migration
• You have development resources and want to build custom integrations against a clean API
• You value rapid feature development and vendor responsiveness

Don't switch just because you're frustrated. Frustration with ConnectWise is often frustration with a bad configuration, not with the platform itself. Before you commit to a migration, get an honest assessment of whether optimizing your current setup would solve the problems that are pushing you toward the door. Sometimes a $5,000 optimization project fixes what a $30,000 migration was supposed to fix.

And don't stay just because switching is scary. If you've genuinely outgrown your current platform's pricing model, if the vendor relationship has deteriorated, or if the platform's direction doesn't align with where your business is going, staying put has its own costs — they're just less visible than a migration invoice.

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Not sure whether to optimize or migrate? Book a discovery call and I'll give you a straight answer based on your specific situation.