Migrating from ConnectWise to HaloPSA: The Field Guide
Bottom Line Up Front: Migrating your PSA is one of the most complex IT operations you'll undertake. This guide reveals what actually trips teams up—data mapping nightmares, RMM integration complexity, SLA translation failures, invoicing breakdowns, client portal transitions, and the ConnectWise API restrictions that changed the game in 2024. Follow these battle-tested checklists and timelines to avoid the costly mistakes that turn straightforward migrations into months-long remediation projects.
Why Teams Are Making the Switch
The Professional Services Automation (PSA) landscape experienced a seismic shift when ConnectWise modified their API terms in 2024, effectively restricting data exports to competing platforms. This policy change transformed what was once a straightforward migration into a strategic decision requiring careful planning and architectural foresight. Meanwhile, HaloPSA has emerged as the platform of choice for MSPs seeking greater flexibility, more powerful automation capabilities, and escape from the private equity-driven pricing pressures that have characterized ConnectWise's recent trajectory.
According to industry analysis, HaloPSA offers significantly more customization options than ConnectWise Manage, with users consistently reporting that tasks can be accomplished "seven different ways" rather than being locked into rigid workflows. However, this power comes with a steep learning curve—the platform's complexity represents both its greatest strength and its most significant adoption barrier. For MSPs managing multiple clients with diverse service delivery requirements, the investment in mastering HaloPSA's capabilities typically pays dividends within the first year of operation.
Reality Check: The True Cost of Migration
Most MSPs dramatically underestimate migration costs. Beyond licensing and migration tools, factor in:
- Staff productivity handicap: Expect 30-40% reduced efficiency for 3-6 months as your team learns HaloPSA's workflows
- Integration rework: Every third-party connection requires reconfiguration, testing, and validation
- Training investment: Budget 40-60 hours per technician for comprehensive platform training
- Parallel operation costs: You'll likely maintain ConnectWise licenses for historical ticket reference unless you implement alternative archival solutions
The ConnectWise API Restriction: What Changed in 2024
In a move that sent shockwaves through the MSP community, ConnectWise modified their terms of service to prohibit exporting data via their API to competing PSA platforms. This restriction fundamentally altered the migration landscape, transforming what was once an API-driven automated migration into a manual CSV export and import process.
What You Can't Do Anymore
- Use ConnectWise API to directly export tickets to HaloPSA
- Maintain automated synchronization during parallel operation periods
- Leverage third-party migration tools that rely on ConnectWise API access
Your Available Options
- Export flat file CSV data from ConnectWise for import into HaloPSA
- Option A: Maintain one ConnectWise license for historical ticket reference (~$99-150/month ongoing cost)
- Option B: Create a searchable archive (see detailed analysis below—this is a custom development project, not a simple export)
- Engage HaloPSA's professional services for implementation assistance
⚠️ The Real Story on Historical Data Archiving
Many guides suggest "just create a searchable archive" as if it's a weekend project. Let's be honest about what this actually requires:
Technical Requirements for DIY Archive:
- Database setup (PostgreSQL/MySQL) with proper schema design for ticket relationships
- ETL process to transform ConnectWise CSV exports into your database structure
- Attachment handling: exporting, storing, and linking thousands of files (potentially GB-TB of data)
- Web interface development with search functionality (full-text search, filtering, sorting)
- Authentication/authorization system to control access by technician role
- Hosting infrastructure (cloud server, backup strategy, SSL certificates)
- Ongoing maintenance, security patches, and support
Realistic Time/Cost Estimates:
- Development Time: 80-120 hours for basic functional system
- Initial Setup Cost: $8,000-15,000 if outsourced to developer
- Ongoing Hosting: $50-150/month depending on data volume
- Maintenance: 10-20 hours/year for updates and issue resolution
Cost-Benefit Analysis: A single ConnectWise license for archival access costs ~$1,200-1,800/year. Building a custom archive costs $8,000-15,000 upfront plus $600-1,800/year ongoing. Unless you need to completely sever the ConnectWise relationship for strategic reasons, maintaining one license is often the more cost-effective solution for at least the first 2-3 years post-migration.
Hybrid Approach: Some MSPs maintain the ConnectWise license initially, then invest in custom archival after 2-3 years when the historical data's business value has depreciated and the ConnectWise sunk cost becomes harder to justify.
Industry experts view this restriction as a short-term disadvantage that actually reinforces the strategic value of migration. The policy demonstrates ConnectWise's approach to customer relationships and highlights why many MSPs are accelerating their transition timelines rather than delaying them. The key is understanding that while the migration path has become more manual, it remains entirely feasible with proper planning and realistic timeline expectations.
What Actually Trips Teams Up: The Five Critical Pain Points
1. Data Mapping: The Hidden Complexity
Data mapping represents the most technically challenging aspect of PSA migration. ConnectWise and HaloPSA use fundamentally different data models, requiring careful translation of every custom field, status value, priority level, and classification scheme your organization has developed over years of operation.
Common Mapping Failures and Solutions
❌ Don't Do This: "We'll map everything 1:1"
Many teams attempt to recreate their entire ConnectWise schema in HaloPSA exactly as it exists. This approach fails because HaloPSA's data structure is fundamentally different, and you end up fighting the platform rather than leveraging its strengths.
✓ Do This Instead:
Use the migration as an opportunity to rationalize your data model. Review your custom fields—most organizations discover 40-60% are no longer actively used. Map only essential fields, then leverage HaloPSA's native capabilities to replace custom workarounds.
❌ Don't Do This: Ignoring relational dependencies
Teams often migrate data entities in isolation without considering how they connect. When tickets reference contacts that don't exist yet, or contracts link to service boards that haven't been created, you create broken relationships that require extensive manual cleanup.
✓ Do This Instead:
Follow the dependency chain: Companies → Sites → Contacts → Contracts → Service Boards → Ticket Types → Tickets. Create a detailed mapping document that identifies every foreign key relationship. HaloPSA's CSV import tools include matching functions—use them to validate relationships before committing data.
❌ Don't Do This: Migrating garbage data
The temptation to migrate everything "just in case" results in HaloPSA instances polluted with duplicate records, obsolete accounts, and incorrect classifications that undermine data quality from day one.
✓ Do This Instead:
Implement strict data quality gates before migration. Deduplicate customer records, archive inactive accounts (don't delete—you'll need them for historical ticket references), and standardize naming conventions. Clean data migrates faster and with fewer errors.
Essential Data Mapping Checklist
2. Tickets and Projects: Preserving Service History
Historical ticket data contains critical institutional knowledge—problem patterns, solution documentation, customer interaction history, and service level performance metrics. Losing this context damages both operational efficiency and client relationships. However, migrating tickets presents unique challenges due to their complex structure and volume.
Critical Decision Point: What Ticket History Should You Migrate?
Most MSPs operate under a false assumption that "all ticket history" must migrate. In reality, the optimal strategy balances historical value against migration complexity and ongoing system performance.
Migrate Fully:
- • Open tickets (all ages)
- • Tickets closed within past 90 days
- • Project tickets regardless of status
- • Tickets with attached documentation (SOPs, configurations)
- • Tickets referenced in active contracts
Archive Instead:
- • Closed tickets older than 90 days for standard support
- • Inactive customer tickets (no activity in 12+ months)
- • Duplicate or test tickets
- • Tickets for decommissioned services
- • Simple "password reset" style tickets with no knowledge value
Ticket Migration Best Practices
Disable HaloPSA Approval Processes During Migration
HaloPSA's approval workflows can interfere with ticket status preservation during import. Navigate to Configuration → Tickets → Ticket Types, edit each ticket type, and set "Start an Approval Process" to No before beginning migration. Re-enable after validation is complete.
Preserve Time Tracking Entries
Time entries contain billable hours data critical for revenue recognition and historical client analysis. Export time entries separately, including: agent name, ticket reference, date/time, duration, charge rate, and billing status. Import these after tickets are migrated to ensure foreign key relationships work correctly.
Handle Internal Notes Separately from Public Updates
ConnectWise distinguishes between internal notes and customer-facing updates. HaloPSA uses a similar model but with different visibility controls. During mapping, explicitly flag which action types should be internal versus visible in the customer portal. Mixing these visibility levels can expose confidential information.
Migrate Attachments Using Cloud Storage Links
Large file attachments bloat CSV imports and frequently fail during processing. Instead, upload attachments to SharePoint, Dropbox, or your document management system, then include links in the ticket notes field. This approach migrates faster and maintains access without database bloat.
Community Horror Story: Don't Make This Mistake
The Scenario: An MSP migrated 15,000 tickets without validating customer and contact relationships first. Result: 8,000+ tickets assigned to "Deleted Contact" with no way to trace the original assignee. They spent six weeks manually researching and correcting assignments.
The Lesson: Run validation queries before importing tickets. Ensure every ticket's customer, site, contact, and assigned agent exists in HaloPSA. Create a default "Migration Fallback" agent for edge cases rather than allowing orphaned records.
Ticket & Project Migration Checklist
3. SLAs: The Translation Challenge
Service Level Agreements define your contractual obligations and directly impact customer satisfaction metrics. The fundamental challenge is that ConnectWise and HaloPSA calculate SLA compliance using different engines with distinct configuration paradigms. A direct translation rarely produces equivalent behavior, requiring careful reconfiguration and extensive testing.
Understanding HaloPSA's SLA Architecture
HaloPSA organizes SLAs hierarchically: Configuration → Contracts → SLA Settings. Each contract can override default SLA rules, providing granular control but requiring explicit configuration at multiple levels. Many teams migrate their SLAs only to discover tickets aren't tracking against them because the hierarchy wasn't properly established.
HaloPSA SLA Hierarchy (top to bottom):
- Global SLA Rules (Configuration → SLA → General Settings) - System-wide defaults
- Ticket Type SLA Rules (Configuration → Tickets → Ticket Types) - Category-specific rules
- Contract SLA Overrides (Customer → Contracts → SLA Setting) - Client-specific agreements
- Priority-Based Response Times - Calculated from ticket priority and the applicable SLA level
⚠️ Common SLA Configuration Error
Teams configure beautiful SLA rules in the global settings but forget to link contracts to those SLA definitions. When tickets are created under these contracts, no SLA is applied because HaloPSA requires an explicit contract-to-SLA mapping.
Fix: After creating SLA definitions, navigate to each contract and set the "SLA Setting" field to the appropriate SLA. Use bulk edit functionality for multiple contracts requiring the same SLA.
SLA Migration Pitfalls and Solutions
❌ Don't Do This: Setting overly aggressive SLAs to "look good"
Many organizations set SLAs that create constant breach conditions, overwhelming teams with red-status tickets and causing agents to ignore SLA notifications entirely. This defeats the purpose of SLA tracking.
✓ Do This Instead:
Analyze your actual historical performance in ConnectWise before migration. Set HaloPSA SLAs at levels your team can realistically achieve 85-90% of the time. Industry research shows that achievable SLAs actually improve performance, while unattainable ones destroy morale and metrics accuracy.
❌ Don't Do This: Forgetting about business hours and holiday calendars
SLAs calculated 24/7 when your team only works 8/5 schedules create artificial breaches during nights and weekends. Similarly, migrating without configuring holiday calendars results in SLA violations during company closures.
✓ Do This Instead:
Configure HaloPSA business hours (Configuration → SLA → Business Hours) before creating SLA rules. Set up holiday calendars for at least the current year. Test SLA calculations by creating test tickets at different times to verify after-hours periods don't count against response times.
❌ Don't Do This: Migrating historical SLA data without context
Some teams attempt to import historical SLA compliance metrics from ConnectWise. These numbers become meaningless in HaloPSA's reporting because the calculation engines differ fundamentally.
✓ Do This Instead:
Treat migration cutover as a "reset" for SLA metrics. Export ConnectWise historical SLA reports as PDFs and archive them. Start fresh SLA tracking in HaloPSA from day one. Document the transition in your reporting to avoid confusion about why metrics changed at cutover.
SLA Configuration Checklist
4. Invoicing: Where Most Migrations Break
Billing and invoicing migration causes more post-cutover emergencies than any other component. When invoicing breaks, cash flow stops—creating immediate business impact that forces teams to rush fixes rather than implementing properly. The complexity stems from HaloPSA's fundamentally different approach to recurring billing, contract value calculation, and integration with accounting systems.
Critical Reality Check
Most teams discover billing issues after cutover, not before. You process your first month-end billing cycle in HaloPSA only to discover contracts aren't generating invoices, charge rates don't match, or time entries aren't calculating correctly. By then, you're operating under pressure to generate invoices while clients wait for their monthly bills. This scenario is entirely preventable with proper pre-cutover testing.
Understanding HaloPSA's Billing Model
HaloPSA treats contract values as recurring invoices rather than fixed contract prices. This architectural difference fundamentally changes how you configure billing. In ConnectWise, you might have a contract with a monthly value of $5,000. In HaloPSA, that same arrangement requires creating a recurring invoice template linked to the contract, which then generates invoice line items on your billing schedule.
HaloPSA Billing Component Hierarchy:
- 1. Billing Descriptions - Define what you're billing for (Managed Services, Project Work, T&M Support)
- 2. Charge Types - Labor rates, product costs, recurring services
- 3. Contracts - Customer agreements with billing periods and payment terms
- 4. Recurring Invoices - Templates that generate on schedule, linked to contracts
- 5. Ready for Invoicing - Staging area where you review and approve invoices before generation
- 6. Invoice Generation - Creates actual invoices, syncs to accounting system if integrated
Each component must be correctly configured and linked. Missing one connection in this chain results in billing failures that manifest as "nothing appears in Ready for Invoicing" or "invoices generate with $0 amounts."
Billing Migration Pitfalls and Solutions
❌ Don't Do This: Migrating contracts without recurring invoice templates
Teams import contracts with all the correct billing amounts and terms, then wonder why nothing appears in Ready for Invoicing. Contracts alone don't generate invoices in HaloPSA—they need associated recurring invoice records that define what gets billed and when.
✓ Do This Instead:
After importing contracts, create recurring invoices for each contract's monthly/quarterly charges. Set the billing description, add line items with correct charge types and amounts, and configure the billing frequency. HaloPSA can then automatically generate invoices according to your schedule.
❌ Don't Do This: Forgetting to map time entry charge rates
Migrated time entries lose their connection to charge rates, resulting in time being billed at $0 or default rates that don't match your actual pricing structure. This error can cost thousands in undercharged billable hours.
✓ Do This Instead:
Create your charge rate structure in HaloPSA before importing time entries. Map each ConnectWise rate to a HaloPSA charge type by name or code. During time entry import, ensure each record includes the charge type reference. Validate a sample of imported time entries to confirm rates applied correctly.
❌ Don't Do This: Testing billing configuration on the first real month-end
Many teams configure billing, assume it works, then discover problems when generating actual client invoices under deadline pressure. This forces rushed fixes that create additional errors.
✓ Do This Instead:
Run a complete billing cycle simulation in your test environment 2-3 weeks before cutover. Create test contracts, log test time entries, add test recurring charges, then generate invoices. Review every invoice for accuracy. This identifies configuration issues while you still have time to fix them systematically.
❌ Don't Do This: Assuming accounting integration "just works"
QuickBooks, Xero, and other accounting integrations require specific field mappings, chart of accounts alignment, and tax code matching. Teams often configure HaloPSA billing perfectly but then can't sync to their accounting system, creating manual data entry overhead.
✓ Do This Instead:
Configure and test your accounting integration before cutover. Map HaloPSA accounts codes to your chart of accounts, configure tax codes, and set up customer matching rules. Generate test invoices and verify they sync correctly with all required fields populated. Document any manual steps required for edge cases.
Pro Tip: The Parallel Billing Period
Smart MSPs run parallel billing for one month: generating invoices in both ConnectWise and HaloPSA, then comparing results before sending client invoices. This safety net catches configuration errors before they impact cash flow.
Schedule your HaloPSA cutover immediately after month-end close in ConnectWise. This gives you a full month to validate HaloPSA billing while ConnectWise invoices are already processed and sent. If HaloPSA's first month has issues, you haven't disrupted client billing.
Invoicing Configuration Checklist
5. RMM Integration: The Hidden Migration Killer
Remote Monitoring and Management (RMM) integration represents the most technically complex and operationally critical component of PSA migration—yet it's consistently underestimated in project planning. Your RMM platform (ConnectWise Automate, Datto RMM, NinjaOne, etc.) serves as the operational heartbeat of your MSP, generating thousands of alerts, managing patches, and maintaining asset inventories. Breaking this connection during migration creates immediate operational blindness that can persist for weeks if not properly planned.
Why RMM Integration Failures Are So Devastating
Unlike billing issues that manifest at month-end or SLA problems that accumulate gradually, RMM integration failures create immediate operational chaos. Alerts stop generating tickets. Patch management workflows break. Asset data becomes stale. Your technicians lose visibility into the infrastructure they're supposed to monitor.
One MSP reported that after their HaloPSA cutover, it took three days to discover their RMM alerts weren't creating tickets—during which time multiple client servers experienced undetected issues. The resulting emergency response consumed 200+ staff hours and damaged client relationships that took months to repair.
Understanding RMM-PSA Integration Architecture
The RMM-PSA relationship involves four distinct data flows, each requiring separate configuration and testing:
1. Asset/Device Synchronization
Your RMM discovers and inventories devices across client networks. This data must flow into HaloPSA's asset management system with correct customer/site mappings. Each device needs proper categorization (server, workstation, network device) and linking to the appropriate contract for billing purposes.
Common Failure: Assets import with generic names like "DESKTOP-ABC123" without site context, making them impossible to associate with specific locations or contracts.
2. Alert-to-Ticket Creation
When your RMM detects issues (disk space low, service failure, backup errors), it must automatically create tickets in HaloPSA with appropriate priority, assignment, and SLA application. This requires mapping RMM alert severities to HaloPSA ticket priorities and routing rules to the correct service queues.
Common Failure: All alerts create low-priority tickets regardless of severity, or alerts create duplicate tickets because deduplication rules weren't configured.
3. Ticket-to-RMM Context Linking
When technicians work tickets in HaloPSA, they need direct links back to the RMM console for remote access, system diagnostics, and patch management. HaloPSA should display device status, recent alerts, and provide one-click access to RMM remote control sessions.
Common Failure: Technicians must manually search the RMM for devices referenced in tickets, destroying efficiency and creating context-switching overhead.
4. Patch Management Workflow Integration
Patch approval processes, maintenance windows, and reboot scheduling must coordinate between the RMM and PSA. HaloPSA needs visibility into pending patches, and the RMM needs to respect maintenance windows defined in contracts.
Common Failure: Patches deploy outside approved windows because maintenance schedules didn't migrate correctly, or patch approval workflows require manual recreation in HaloPSA.
RMM Migration Pitfalls and Solutions
❌ Don't Do This: Assuming "native integration" means "works automatically"
HaloPSA advertises native integrations with major RMM platforms, leading teams to assume configuration is plug-and-play. In reality, each integration requires extensive field mapping, threshold configuration, and workflow customization to match your existing operational procedures.
✓ Do This Instead:
Allocate 20-30 hours specifically for RMM integration configuration and testing. Document your current ConnectWise-RMM workflows (what alerts create tickets, what priority levels apply, what routing rules exist). Recreate these workflows explicitly in HaloPSA rather than assuming default behaviors will match.
❌ Don't Do This: Migrating assets without site/location context
RMM systems export assets with technical identifiers (hostnames, IP addresses, MAC addresses) but often lack the customer/site hierarchy needed for PSA integration. Importing these creates thousands of orphaned assets that can't be linked to customers or contracts.
✓ Do This Instead:
Before asset import, create a mapping table linking RMM client IDs to HaloPSA customer IDs and RMM location IDs to HaloPSA site IDs. Use this during import to ensure every asset lands in the correct organizational context. Validate with spot checks: can you navigate from customer → site → assets and see the correct devices?
❌ Don't Do This: Testing RMM integration with a handful of test alerts
Teams create 5-10 test alerts to verify tickets generate, declare success, then discover during production that alert storms create ticket floods, deduplication doesn't work, or specific alert types fail to trigger ticket creation.
✓ Do This Instead:
Conduct load testing with realistic alert volumes. Trigger 50-100 alerts simultaneously to test deduplication logic. Test every alert severity level and type your RMM generates. Verify that resolved alerts close tickets appropriately. Document any alert types that require special handling.
❌ Don't Do This: Forgetting about custom RMM scripts and automation
Many MSPs have custom RMM scripts that create tickets via ConnectWise API, update ticket status based on remediation results, or add notes to existing tickets. These break silently during migration because they reference ConnectWise-specific endpoints and data structures.
✓ Do This Instead:
Audit all custom scripts and automation workflows that touch ConnectWise. Create an inventory with business criticality ratings. Rewrite high-priority scripts for HaloPSA's API before cutover. For lower-priority automations, plan post-migration development sprints rather than blocking go-live.
Pro Tip: The Parallel RMM Monitoring Period
For the first week after cutover, maintain connections to both ConnectWise and HaloPSA from your RMM. Configure your RMM to create tickets in both systems simultaneously. This provides a safety net—if HaloPSA ticket creation fails, the ConnectWise ticket ensures nothing falls through the cracks.
Compare ticket volumes daily: HaloPSA should generate approximately the same number of RMM-triggered tickets as ConnectWise. Significant discrepancies indicate configuration problems requiring immediate investigation. Once you achieve 95%+ parity for three consecutive days, decommission the ConnectWise connection.
RMM Integration Checklist
The Often-Forgotten Stakeholder: Managing Client-Facing Changes
While technical teams focus intensely on internal system migration, the customer-facing transition often receives inadequate attention—creating confusion, support ticket spikes, and damaged client relationships precisely when your organization needs operational stability. Your clients don't care about PSA migration complexity; they only care that their ticket submission process changed, their portal looks different, and their invoices arrive in unfamiliar formats.
The Client Impact You Cannot Ignore
From your clients' perspective, PSA migration represents forced change to tools and processes they've mastered over years of use. Inadequate client change management creates three immediate problems:
- Support Volume Spike: Clients flood your helpdesk with questions about the "new system" they didn't ask for, consuming technician capacity precisely when your team needs to focus on internal stabilization.
- Perception of Instability: Clients interpret system changes as evidence of internal chaos, raising questions about your operational competence and potentially triggering contract reviews.
- Workflow Disruption: Power users who developed efficient ticket submission patterns must relearn processes, creating frustration and temporary productivity losses on their end.
What Changes for Your Clients
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Portal URL & Appearance: Complete visual redesign with new login page, navigation structure, and workflow patterns
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Ticket Submission Process: Different form fields, category selections, and attachment handling
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Email Notifications: New sender addresses, different formatting, altered notification triggers
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Invoice Format: Different layout, line item descriptions, and payment instructions
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Knowledge Base Access: If you maintain customer-facing documentation, URLs and search functionality change
What Stays The Same (Emphasize This!)
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✓
Your Contact Information: Phone numbers, email addresses, and emergency contacts remain unchanged
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✓
Service Delivery: Response times, SLA commitments, and support coverage hours stay consistent
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✓
Your Team: Same technicians, account managers, and escalation contacts
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✓
Contract Terms: Pricing, billing cycles, and service agreements remain in effect
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✓
Historical Data: Ticket history and documentation remain accessible
Client Communication Strategy & Timeline
3 Weeks Before Cutover: Initial Announcement
Send a positive, benefit-focused email to all client contacts explaining the upcoming improvement to your service delivery platform. Key messaging points:
- Frame as an upgrade, not a migration (emphasize improved features, faster response times, better portal)
- Specific cutover date and any expected brief service interruptions
- What will change (portal URL, email notifications) and what stays the same (phone numbers, contacts, SLAs)
- Provide preview screenshots of new portal interface
- Offer optional live training webinar for power users
1 Week Before Cutover: Detailed User Guide
Send a comprehensive "What You Need to Know" guide with practical instructions:
- Step-by-step portal login instructions with screenshots
- How to submit tickets in the new system (include video walkthrough)
- New email addresses to whitelist for notification delivery
- PDF quick-reference card for printing and desk distribution
- FAQ addressing common concerns ("Can I still email tickets?" "Where's my history?")
Cutover Weekend: Status Updates
Maintain communication transparency during transition:
- Friday evening: "Migration in progress, ticketing temporarily unavailable via portal. Phone/email support fully operational."
- Sunday afternoon: "Migration complete! New portal live at [URL]. Email your account manager if you need login assistance."
- Include direct phone number for immediate assistance rather than forcing portal use during transition chaos
First Week Post-Cutover: Proactive Support
Implement enhanced client support measures:
- Assign "migration support" designation to 2-3 technicians as dedicated first-line responders for portal questions
- Call top 10-20 clients personally to ensure smooth transition and offer hands-on portal walkthrough
- Monitor support ticket volumes for unusually high "how do I" questions indicating communication gaps
- Send "thank you for your patience" message Friday afternoon acknowledging any inconvenience
2 Weeks Post-Cutover: Feedback Collection
Gather insights for ongoing improvement:
- Send brief survey (3-5 questions) about new portal experience
- Ask specifically: "What took you longest to figure out?" and "What would improve your experience?"
- Use feedback to create additional training materials or process improvements
- Publicly acknowledge feedback and communicate any resulting changes
Special Considerations: VIP & High-Touch Clients
Your largest accounts and most technically sophisticated clients require white-glove treatment during PSA transitions. Do not rely solely on mass communications for these relationships.
VIP Client Protocol:
- Schedule personal meetings 2-3 weeks before cutover to preview changes and address concerns
- Provide dedicated hotline phone number for migration weekend (bypassing normal support queues)
- Offer custom training sessions for their entire IT team if requested
- Assign specific account manager as single point of contact throughout transition
- Follow up personally within 48 hours post-cutover to ensure satisfaction
These accounts represent significant revenue and reference value. The extra investment in personalized transition management prevents the retention risks that arise when major clients feel deprioritized during internal operational changes.
Client Change Management Checklist
The Cutover Timeline: Your 8-Week Roadmap
Successful PSA migrations follow a phased approach that balances thorough preparation with decisive execution. This timeline represents the industry best practice drawn from organizations that completed migrations with minimal business disruption. Adjust phases based on your organization size, data volume, and complexity—but don't skip steps.
Weeks 1-2: Discovery & Planning
Goal: Complete data assessment and establish migration architecture before any technical work begins.
🔍 Data Inventory & Quality Assessment
- Export full data model documentation from ConnectWise
- Identify custom fields, workflows, and integrations requiring migration
- Run data quality reports: duplicate detection, orphaned records, incomplete fields
- Document integration touchpoints (RMM tools, accounting systems, documentation platforms)
👥 Team Formation & Responsibility Assignment
- Designate migration project manager (not part-time role—dedicate 100% focus)
- Assign data owners for each major entity (tickets, contracts, billing, etc.)
- Identify key power users for HaloPSA training pilot group
- Establish executive sponsor for escalation authority and budget approval
📋 Decision Framework Documentation
- Define ticket history cutoff date based on retention requirements and data volume
- Choose cutover approach: big bang vs. phased (most choose big bang for PSA migrations)
- Establish rollback criteria and fallback procedures
- Set cutover date targeting post-month-end for billing cycle alignment
Weeks 3-4: Environment Setup & Data Mapping
Goal: Configure HaloPSA production environment and complete detailed field-level mappings.
⚙️ HaloPSA Configuration
- Provision HaloPSA instance and configure company/branding settings
- Create user accounts for all agents with appropriate permission levels
- Configure ticket types matching your service delivery categories
- Set up business hours, holiday calendars, and timezone settings
- Enable required modules: Billing, Contracts, Projects, Asset Management
🗺️ Detailed Field Mapping
- Create field mapping spreadsheet: CW Field → Halo Field → Transformation Rules
- Map all dropdown values: statuses, priorities, categories, types
- Define data cleansing rules for standardization during import
- Document fields that won't migrate and create manual workaround procedures
🔌 Integration Architecture
- Configure RMM integration (ConnectWise Automate, Datto RMM, etc.) - allocate 20-30 hours for proper setup
- Set up accounting system integration with credential exchange and field mapping
- Documentation Platform Integration (Critical): Reconnect IT Glue/Hudu to HaloPSA
⚠️ Documentation Platform Integration: Don't Underestimate This
If you use IT Glue, Hudu, or similar documentation platforms, reconnecting these to HaloPSA is tedious and error-prone. You're not just changing an API endpoint—you're remapping thousands of relationships.
- Every customer in your documentation platform must be re-linked to corresponding HaloPSA customer records
- Asset relationships between PSA and documentation require manual verification
- Embedded links in documentation articles pointing to ConnectWise tickets become broken references
- Custom fields synchronized between platforms need field mapping recreation
- Testing requirement: Can technicians access documentation from tickets? Do asset records sync correctly?
Budget 15-25 hours for documentation platform integration, mapping validation, and broken link remediation. This isn't installation—it's relationship reconstruction across potentially thousands of records.
- Configure SSO/SAML for user authentication if required
Weeks 5-6: Data Migration & Testing
Goal: Execute data migration in staging environment and validate results before production cutover.
📦 Phased Data Import (follow this sequence)
- Companies/Customers: Import company records with sites and locations
- Contacts: Import all customer contacts with role assignments
- Contracts: Import contracts with terms, billing periods, SLA assignments
- Assets: Import asset inventory with customer/site relationships
- Service Boards & Ticket Types: Recreate your queue structure
- Tickets (in batches): Import 1000 tickets at a time to manage errors
- Time Entries: Import after tickets exist to maintain foreign key integrity
- Recurring Invoices: Create billing templates for contract charges
✅ Validation Testing
- Statistical sampling: validate 5% of each data entity for accuracy
- Relational integrity checks: verify ticket-to-customer, contract-to-customer mappings
- SLA calculation testing: create tickets at different priorities and validate timers
- Billing simulation: run complete month-end cycle and review generated invoices
- Integration testing: verify data flows correctly to/from connected systems
🎓 User Training Pilot
- Train power user group (5-8 people) on HaloPSA workflows
- Have power users complete actual work in test environment
- Document questions, confusion points, and workflow gaps
- Refine configuration based on user feedback before broad rollout
Week 7: Training & Preparation
Goal: Ensure entire team is trained and all stakeholders understand cutover procedures.
👨🏫 Organization-Wide Training
- Conduct role-based training sessions: technicians, dispatchers, managers
- Cover essential workflows: ticket creation, time tracking, customer portal
- Create quick-reference guides and video tutorials for common tasks
- Schedule drop-in Q&A sessions throughout the week
📢 Communication & Stakeholder Management
- Send customer communication about portal changes and new ticket submission process
- Notify vendors/partners about new support contact methods if applicable
- Brief leadership team on cutover timeline and expected support load
- Establish war room schedule for cutover weekend support
🔄 Final Preparation
- Freeze ConnectWise configuration changes (no new custom fields, workflow modifications)
- Complete final data export from ConnectWise
- Validate backup restoration procedures for rollback scenario
- Confirm all team members have HaloPSA credentials and system access
Week 8: Cutover & Go-Live
Goal: Execute cutover with minimal disruption and establish hypercare support for first week.
🎯 Cutover Weekend (Friday Evening - Sunday)
Friday 6:00 PM - Cutover Initiation
- Set ConnectWise to read-only mode or disable ticket creation
- Export final delta data: any tickets/time created since last export
- Begin final data import into HaloPSA production
Saturday 9:00 AM - Validation Phase
- Run complete validation suite: data accuracy, relationships, calculations
- Test critical workflows: ticket creation, time entry, SLA tracking
- Generate test invoice batch to confirm billing readiness
- Verify integrations passing data correctly
Sunday 12:00 PM - Go/No-Go Decision Point
- Executive sponsor reviews validation results
- Decision: proceed with go-live or execute rollback
- If go-live: update DNS/customer portal URLs to HaloPSA
- Send go-live confirmation to all stakeholders
🚑 Week 1 Hypercare Support
- Staff war room with HaloPSA experts for immediate issue resolution
- Hold daily standup meetings to address blockers and confusion points
- Monitor system performance, integration health, and error logs
- Document issues and workarounds in shared knowledge base
- Collect user feedback for configuration refinements
✅ Success Criteria for Go-Live Approval
- 95%+ data validation pass rate across all entities
- All critical integrations passing health checks
- SLA calculations producing expected breach/compliance times
- Test billing cycle generating accurate invoice amounts
- User login success rate >98% (no authentication issues)
- Zero critical defects; any medium-severity issues have documented workarounds
Timeline Modification Factors
This 8-week timeline assumes a mid-sized MSP (10-30 employees, 50-150 clients). Adjust based on:
- Organization Size: Add 1-2 weeks for 30+ employees requiring coordination
- Data Volume: Add 1-2 weeks if migrating 10,000+ tickets or 5+ years of history
- Integration Complexity: Add 1 week per complex integration (custom APIs, legacy systems)
- Customization Level: Add 2-3 weeks if ConnectWise has extensive custom fields/workflows
- Team Experience: Reduce by 1-2 weeks if you have HaloPSA-experienced staff
Post-Cutover: The First 30 Days
The cutover weekend represents the beginning of your migration, not the end. The subsequent 30 days determine whether your migration succeeds or becomes a costly false start requiring remediation. Organizations that treat post-cutover as an afterthought typically experience 30-40% productivity drops that persist for months. Strategic post-cutover management limits this impact to 15-20% for 2-3 weeks.
Stabilization Phase
- • War room operational daily
- • All hands on deck support
- • Issue triage and rapid fixes
- • Data quality spot checks
- • Integration monitoring
Optimization Phase
- • Workflow refinement based on usage
- • Additional training for struggling users
- • Performance tuning
- • Report/dashboard creation
- • Process documentation updates
Normalization Phase
- • First month-end billing cycle
- • Reduced support coverage
- • Lessons learned documentation
- • Decommission ConnectWise (or archive)
- • Celebrate with team!
First Month-End Billing: Your Final Validation
The first billing cycle in HaloPSA serves as the ultimate migration validation. This is where missed contract configurations, incorrect charge rates, and broken accounting integrations reveal themselves. Don't wait until the last day of the month to discover problems.
Run a practice billing cycle on Day 15: process a subset of contracts through to invoice generation and accounting sync. This gives you two weeks to fix any issues before real month-end arrives. Document the exact process for future reference—your billing procedures in HaloPSA will differ from ConnectWise workflows.
When to Call for Professional Help
Not every organization should attempt self-service PSA migration. The time investment, technical complexity, and business risk often justify engaging professional services—particularly for organizations lacking dedicated project management resources or MSPs managing 100+ clients with complex service agreements.
Red Flags: You Need Professional Help If...
- ⚠️ Your team has never performed a major system migration before
- ⚠️ ConnectWise contains 5+ years of data with extensive customizations
- ⚠️ You're managing 150+ clients with complex multi-tier service agreements
- ⚠️ Your billing processes involve custom integrations or unusual arrangements
- ⚠️ The migration timeline is critical due to contract changes or other deadlines
- ⚠️ Staff capacity is already maxed out with normal operations
You Can Self-Migrate Successfully If...
- ✅ You have dedicated project management resources (not wearing other hats)
- ✅ Your ConnectWise configuration is relatively standard without extensive customization
- ✅ You're managing fewer than 75 clients with straightforward billing structures
- ✅ You have 10-12 weeks available for careful, methodical migration work
- ✅ Your team includes technically proficient members comfortable with data manipulation
- ✅ You can tolerate 2-3 weeks of reduced productivity post-cutover
Professional Services Options
HaloPSA Implementation Services
HaloPSA offers official implementation assistance that includes data migration support, configuration guidance, and training. Their team has completed hundreds of migrations and understands the nuances of their platform better than anyone. Pricing varies based on scope, but typically ranges from $5,000-15,000 for mid-sized implementations.
Third-Party Migration Specialists
Specialized firms like Gozynta and others focus exclusively on PSA migrations. They bring experience across multiple platforms and can often complete migrations faster than in-house teams. Consider this option if you're on a tight timeline or need the highest reliability guarantee.
Hybrid Approach: Consulting + Internal Execution
Many successful migrations use consultants for the complex pieces (data mapping, billing configuration, integration setup) while handling straightforward tasks internally. This balances cost with expertise and often proves most cost-effective for mid-sized organizations.
How ITECS Online Can Support Your Migration
At ITECS Online, we understand that PSA migrations represent critical infrastructure transitions that can't afford to fail. Our team has guided numerous Dallas-area MSPs through complex technology transformations, bringing the methodical approach and risk management expertise that ensures business continuity throughout the migration process.
Migration Support Services
Pre-Migration Assessment
We analyze your ConnectWise configuration, identify migration complexity factors, and provide realistic timeline and resource estimates before you commit to the project.
Data Architecture Review
Our consultants map your data model, identify quality issues, and create detailed transformation specifications that prevent the errors that derail most migrations.
Integration Strategy
We design integration architecture connecting HaloPSA to your RMM, accounting, and documentation platforms—ensuring seamless data flow across your technology stack.
Billing Configuration
Our team specializes in complex billing migrations—configuring HaloPSA's invoicing engine to match your existing agreements and ensuring first-month billing accuracy.
Beyond Migration: Long-Term Success
Migration success extends beyond cutover weekend. ITECS Online provides ongoing IT consulting services to optimize your HaloPSA configuration as your business evolves. We help Dallas MSPs leverage advanced features like automation workflows, custom reporting, and API integrations that transform PSA platforms from ticket trackers into strategic business intelligence systems.
Our managed IT services include comprehensive system monitoring and backup and disaster recovery solutions that protect your newly migrated PSA data. With enterprise-grade security frameworks and proactive management, we ensure your critical business systems remain operational and secure.
Final Thoughts: Migration as Strategic Opportunity
PSA migration forces you to examine every aspect of your service delivery operation. While this scrutiny feels overwhelming during planning phases, it represents a unique opportunity to eliminate accumulated technical debt, rationalize overcomplicated workflows, and establish best practices that may have eroded over years of incremental changes.
Organizations that approach migration purely as "moving data from System A to System B" typically recreate all their existing problems in the new platform. The most successful migrations use the transition as a catalyst for operational improvement—questioning assumptions about ticket categorization, streamlining SLA structures, and eliminating unused custom fields that cluttered the old system.
Ready to Begin Your HaloPSA Migration?
Don't let migration complexity delay your technology modernization. Schedule a consultation with ITECS Online to receive a customized migration assessment, realistic timeline projections, and expert guidance that transforms a daunting transition into a strategic advantage for your MSP.
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