What I Learned Migrating MSPs from ConnectWise to HaloPSA

The ConnectWise-to-HaloPSA migration has become the most common PSA switch in the MSP world. I don't think that's controversial at this point — HaloPSA's growth numbers speak for themselves, and the community sentiment around ConnectWise pricing and contracts has been pushing people toward alternatives for a while now.

I've handled several of these migrations, and every single one has taught me something. Here are the lessons that keep coming up.

The agreement structure doesn't translate one-to-one

This catches people off guard more than anything else. ConnectWise and HaloPSA handle recurring billing fundamentally differently under the hood, and you can't just export ConnectWise agreements and import them into HaloPSA.

ConnectWise agreements have additions, exclusions, board coverage rules, and a specific relationship between work types and billing. HaloPSA's billing uses contracts with recurring invoices, billing templates, and a different paradigm for what's covered versus billable.

The concept maps — both platforms track recurring services and bill clients monthly — but the implementation details diverge enough that every agreement needs to be rebuilt in HaloPSA's structure, not migrated mechanically. Plan for this. It takes time, it requires understanding both platforms' billing models, and it's the area where mistakes have direct financial consequences.

I build a mapping document for every migration that shows each ConnectWise agreement, its components, and the corresponding HaloPSA contract configuration. The client reviews and approves this mapping before we build anything. It's tedious but it prevents billing errors on day one.

Workflow rules need to be redesigned, not translated

Your ConnectWise workflow rules were written for ConnectWise's specific trigger events, condition structure, and action capabilities. HaloPSA has its own automation engine with different triggers, different conditions, and different actions.

The mistake I see people make is trying to recreate their ConnectWise workflow rules verbatim in HaloPSA. Don't do that. Instead, start from the business outcome each rule achieves and design the HaloPSA implementation from scratch.

For example, ConnectWise might use a workflow rule chain where Rule A changes a ticket status, which triggers Rule B to send a notification, which triggers Rule C to set a timer. In HaloPSA, that entire sequence might be handled by a single automation with multiple actions, or it might use a completely different mechanism like SLA cascades.

Translation fails. Redesign works.

The email parser transition is trickier than expected

Almost every MSP has email-to-ticket parsing configured in ConnectWise. Clients send emails to support@yourmsp.com, ConnectWise ingests them, creates or updates tickets, and threads the conversation.

When you switch to HaloPSA, that email parser needs to be reconfigured from scratch. The way HaloPSA handles email ingestion, thread matching, and ticket updates is different. The specific parsing rules, exclusions, and routing logic need to be rebuilt.

More importantly, the transition itself has a gap risk. At the moment you switch your email flow from ConnectWise's parser to HaloPSA's parser, any emails that arrive during the transition window might not get captured correctly. I schedule parser switchovers for low-volume windows (typically early Sunday morning) and manually verify that the first batch of emails parse correctly before walking away.

Also — and this bites people — check your email signatures. ConnectWise and HaloPSA handle signature stripping differently. If your parser doesn't strip signatures properly, tickets fill up with repeated signature blocks in every update, making the conversation thread unreadable.

ConnectWise's data export has gotten more complicated

I mentioned this in my migration post already, but it bears repeating specifically in the CW-to-Halo context. ConnectWise's terms of service changes around API usage for data export to competing platforms have added friction to the migration process.

The way I handle this: work with ConnectWise's own data export tools where possible, supplement with direct database access when the MSP hosts their own instance or can request database exports from ConnectWise, and use the REST API only for data types that aren't restricted.

This isn't a showstopper, but it adds planning time and sometimes limits the completeness of historical data migration. Be upfront with your team about what will and won't transfer cleanly.

HaloPSA's learning curve is different, not absent

A common misconception: "HaloPSA is easier, so our team won't need much training." HaloPSA's interface is more modern and more intuitive than ConnectWise's, but it's still a complex professional platform with its own logic and conventions.

The areas where teams struggle most in the first few weeks:

The admin panel configuration is deep. HaloPSA's settings are organized differently than ConnectWise's, and the person managing the platform needs dedicated time to learn where things live.

Custom fields and ticket templates work differently. Teams that were used to ConnectWise's custom field system need to learn HaloPSA's approach to fields, forms, and templates.

The reporting engine is different. Any custom reports from ConnectWise need to be rebuilt, and the query structure is not the same.

Invest in training. Real training, not "here's a login, figure it out." The payback period on training investment is about two weeks — that's how quickly you see the productivity difference between a trained team and one that's fumbling.

The integrations that cause the most headaches

From my experience, ranked by difficulty of reconnection:

Easiest: M365 integration, basic RMM alerting, calendar sync.

Moderate: Accounting platform sync (QuickBooks/Xero — field mappings change), documentation platform (ITGlue/Hudu — different linking structure), monitoring tool alert routing.

Hardest: Custom API integrations built specifically for ConnectWise, Rewst automations that reference ConnectWise-specific endpoints, any integration that relies on ConnectWise's proprietary callback structure.

For any custom integration, budget dedicated development time for the rebuild. A ConnectWise-specific API integration doesn't magically become a HaloPSA integration — it needs to be rewritten against HaloPSA's API.

The timeline that actually works

For a ConnectWise-to-HaloPSA migration with a team of 10–25 people and 200–500 managed endpoints:

Weeks 1–2: Discovery, data audit, integration inventory, agreement mapping. Weeks 3–5: HaloPSA environment build — tickets, boards, SLAs, automations, billing, user setup. Weeks 6–7: Data migration (staged, with validation). Weeks 8–9: Integration reconnection and testing. Week 10: Team training (role-specific). Week 11: Cutover (Friday evening) with weekend stabilization. Weeks 12–14: Post-migration support window.

That's 14 weeks. Three and a half months. You can compress it if the MSP is small and simple. You should expand it if the environment is complex or if there are a lot of custom integrations.

Was it worth it?

Every MSP I've migrated from ConnectWise to HaloPSA has, once the dust settled and the team was up to speed, said yes. The licensing savings are real. The interface improvement is real. The API quality difference is real. HaloPSA's development velocity matters.

But every single one of them also said it was harder than they expected, took longer than they planned, and that they wished they'd invested more in planning and training up front. That feedback is remarkably consistent, and it's why I front-load planning and training in every migration I run.

The decision to migrate is a business decision that should be made on total cost of ownership, strategic alignment, and operational fit — not on frustration alone. But when the numbers work, the execution goes well, and the team embraces the new platform, the results are genuinely positive.

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Thinking about making the switch? Book a discovery call and I'll help you figure out if it makes sense for your specific situation.