Why Migrate from ConnectWise to Aerie OS?

ConnectWise has served MSPs well for years. It's reliable, widely adopted, and the integration ecosystem is mature. But as your business grows, you'll hit its limitations:

Per-seat licensing: ConnectWise charges per technician, but doesn't include CRM, documentation, or password management. You end up buying Salesforce, IT Glue, and LastPass on top.
Limited automation: Rule-based workflows are basic. No visual workflow builder. No AI-powered routing.
Data silos: Tickets, contracts, quotes, and financials live in separate systems. Your team switches between tabs constantly.
Vendor fatigue: You're managing ConnectWise + 3–5 integration partners. That's 3–5 contracts, 3–5 vendor relationships, 3–5 support channels.

Aerie OS solves this by bundling PSA, RMM, CRM, security, documentation, and compliance into one unified platform—all designed for modern MSP workflows.

This guide walks you through the migration process honestly. Migration takes effort. Some ConnectWise data migrates cleanly; some requires manual work. This guide tells you which is which, so you can plan realistically.

Pre-Migration: What You Need to Know

1. What Data Migrates and What Doesn't

Migrates cleanly (automated):

Clients (accounts and contacts)
Contracts and service schedules
Tickets and ticket history
Assets and hardware inventory
Companies and business unit structure
Billing and invoice records (via CSV import)

Requires manual effort:

Custom fields (need to be manually recreated in Aerie)
Ticket templates and workflow rules (need reimplementation in Aerie's workflow builder)
Automations (ConnectWise rules must be manually rebuilt as Aerie workflows)
Integrations (third-party tools need reconfiguration in Aerie)
RMM data (if you use ConnectWise RMM, you're starting fresh with Aerie's native RMM)
CRM customizations (sales pipeline stages, deal fields, etc.)

Does not migrate (plan ahead):

ConnectWise RMM agents (decommission ConnectWise RMM; deploy Aerie RMM agents)
IT Glue/Hudu documentation (manually migrate to Aerie's Wiki and Scribe)
Salesforce/CRM data (if you use external CRM, migrate manually or use a third-party sync tool)

2. License and Subscription Considerations

Before migration:

Calculate your current total cost: ConnectWise + IT Glue + RMM + CRM + password manager + integrations.
Compare to Aerie: one per-technician price includes all modules.
Plan your Aerie licence: one per active technician (optional: add observer seats for management/admin staff at a lower rate).

During migration:

You'll run both systems in parallel for 2–4 weeks. This means paying for both simultaneously. Budget accordingly.
You don't need to maintain ConnectWise RMM agents during parallel running—decommission them before cutover.

After cutover:

Cancel ConnectWise (and IT Glue, external RMM, etc.) at the end of your billing cycle to avoid pro-rata refunds.

Migration Timeline: What to Expect

Realistic timelines depend on your MSP size and data complexity:

For a small MSP (1–5 techs, <50 clients, <2 years of historical data):

Pre-migration planning: 1 week (define custom fields, plan workflows, user access model)
Data export and import: 2–3 days (run test import, validate, tweak)
Parallel running: 1–2 weeks (staff trained, running both systems, validating completeness)
Cutover and cleanup: 1 day (final validation, disable ConnectWise, activate Aerie in production)
Post-migration stabilisation: 1–2 weeks (bug fixes, tuning, addressing edge cases)
Total: 2–4 weeks

For a mid-market MSP (10–30 techs, 200–500 clients, 5+ years of data):

Pre-migration planning: 2–3 weeks (define custom fields, audit data quality, plan integration rewiring)
Data export and import: 1 week (initial import, validation, large dataset testing)
Parallel running: 3–4 weeks (phased team training, gradual client cutover)
Cutover and cleanup: 2–3 days (final validation, integration testing, ConnectWise decommission)
Post-migration stabilisation: 3–4 weeks (performance tuning, custom workflows, integration fixes)
Total: 6–10 weeks

For a large MSP (50+ techs, 1000+ clients, 10+ years of data):

Pre-migration planning: 4–6 weeks (full audit, team alignment, integration architecture)
Data export and import: 2–3 weeks (large dataset handling, incremental sync strategy)
Parallel running: 4–6 weeks (phased team rollout by department, per-client transition)
Cutover and cleanup: 3–5 days (staged cutover, per-geography or per-business-unit)
Post-migration stabilisation: 6–8 weeks (performance optimisation, integration tuning, staff retraining)
Total: 15–25 weeks

Reality check: These timelines assume:

Your ConnectWise data is reasonably clean (most organisations have some data quality issues).
You have a dedicated person (or team) managing the migration.
You have direct access to ConnectWise API and export tools.
Your team is willing to learn new processes (Aerie is different, and that's intentional).

If your data is messy or you're understaffed, add 50% to these estimates.

Step-by-Step Migration Process

Phase 1: Pre-Migration Planning (Weeks 1–2)

1.1 Audit Your ConnectWise Data

Before you export anything, understand what you're exporting:

Run these checks:

How many active clients? How many archived/inactive?
How much historical ticket data? (Last 12 months? 5 years?)
How many custom fields do you use? (List them—you'll need to recreate them.)
How many ticket automations/workflows exist? (List the logic—you'll rebuild these in Aerie.)
How many integrations connect to ConnectWise? (Zapier, Slack, accounting software, etc.)

Output: A simple spreadsheet documenting:

Item	Count	Notes
Active clients
Archived clients
Tickets (last 12mo)
Custom ticket fields
Custom client fields
Automations
Integrations

1.2 Plan Your Aerie OS Configuration

Aerie's structure is different from ConnectWise. Plan ahead:

Clients → Companies: In Aerie, "Company" = what ConnectWise calls "Client." Plan your company hierarchy (parent companies, business units, departments).
Users and permissions: Decide who gets access to what. Aerie has granular permission controls—more granular than ConnectWise. Plan your team structure.
Custom fields: List which custom fields you actually use vs. which are legacy cruft. Recreate only the ones you need.
Ticket types/categories: Plan your ticket classification (problem, request, incident, etc.). Align with Aerie's default categories.
Contract management: How do you manage contracts in Aerie? Flat structure or by company? Plan this now.

1.3 Document Your ConnectWise Workflows and Automations

For each workflow/automation in ConnectWise, document:

Trigger: What event causes the workflow to fire? (New ticket, status change, SLA breach, etc.)
Condition: What conditions must be true? (Ticket type = "Problem", Priority = "Critical", etc.)
Action: What happens? (Assign to group, create activity, send notification, etc.)

Example:

Trigger: New ticket created
Condition: Ticket type = "Problem" AND Priority = "Critical"
Action: Assign to Senior Tech group, send email to manager, create 2-hour SLA

You'll rebuild these in Aerie's visual workflow builder. Document them now so nothing is forgotten.

Phase 2: Data Export and Import (Weeks 3–4)

2.1 Export Data from ConnectWise

ConnectWise provides multiple export options:

Option A: Use ConnectWise API (Recommended)

Aerie can ingest data directly from the ConnectWise API.
More reliable than manual exports, especially for large datasets.
Real-time data—no stale exports.
Contact Aerie Support to set up API-to-API migration.

Option B: Manual CSV Export

Go to Admin → Exports in ConnectWise.
Export: Clients, Contacts, Tickets, Assets, Contracts, Invoices.
Save as CSV files.
Ensure all dates are in ISO 8601 format (YYYY-MM-DD).

Option C: Third-Party Migration Tool

Tools like Migrate.io or Kernal.io can automate ConnectWise→Aerie migrations.
Adds cost (typically £2,000–5,000) but saves 2–3 weeks of manual work.
Recommended for mid-market and larger MSPs.

2.2 Prepare Data for Import

Before importing, clean your data:

Remove duplicates: ConnectWise often accumulates duplicate client records (typos, old records). Deduplicate now.
Fix date formats: Ensure all dates are ISO 8601 (YYYY-MM-DD).
Standardise phone numbers: Remove formatting inconsistencies.
Flag archived data: Decide what to archive vs. import. (You probably don't need tickets from 2010. Save them as a CSV backup, but don't import.)
Remove invalid relationships: Delete orphaned tickets (tickets with no client), broken asset links, etc.

Quick quality check:

- Do all clients have names? (Search for blank/null client names)
- Do all tickets have a client? (Search for orphaned tickets)
- Are all phone numbers in one format? (UK numbers should start +44 or 020)
- Are all email addresses valid? (No typos like "john@@example.com")

2.3 Perform Test Import

Before importing to production:

Ask Aerie Support for a test tenant.
Import a sample of your data (e.g., 5 active clients, 100 recent tickets, 50 assets).
Validate in the test environment:
- Are client names correct?
- Are ticket details intact?
- Are relationships preserved (ticket → client)?
- Are date fields correct (creation date, due date, etc.)?
- Are custom fields present? (Some may be missing if not mapped.)
Document any issues. Work with Aerie Support to resolve.
Once test import is successful, proceed to full import.

2.4 Full Data Import

Run the full import to your production Aerie tenant. This typically takes:

Small dataset (<5,000 tickets): 30 minutes
Medium dataset (5,000–50,000 tickets): 2–4 hours
Large dataset (50,000+ tickets): 4–12 hours

Aerie will provide a migration report:

Records imported successfully
Records with warnings (e.g., missing fields)
Records that failed

Address failures immediately. Most failures are fixable (reformat a date, trim whitespace, etc.). Don't move forward with unresolved failures.

Phase 3: Configuration and Customisation (Week 4–5)

3.1 Recreate Custom Fields

In Aerie:

Go to Settings → Custom Fields
For each custom field from ConnectWise, create a matching field in Aerie
Map data types (text → text, dropdown → select, date → date, etc.)
Manually backfill values if necessary (Aerie can do bulk updates via CSV)

3.2 Rebuild Workflows and Automations

In Aerie:

Go to Automation → Workflows
For each workflow from your ConnectWise audit, create an equivalent Aerie workflow
Use Aerie's visual workflow builder (drag-and-drop, no code)
Test each workflow with a test ticket

Example: Critical ticket auto-assignment

ConnectWise rule:

IF ticket_type = "Problem" AND priority = "Critical"
THEN assign to "Senior Tech" group
AND create 2-hour SLA

Aerie workflow:

Trigger: New ticket created
Condition: ticket_type equals "Problem" AND priority equals "Critical"
Action 1: Assign to group "Senior Tech"
Action 2: Set SLA to 2 hours

3.3 Configure Integrations

Aerie integrates with:

Slack, Teams, Discord (notifications)
Zapier, n8n, Make (automation)
Stripe, Xero, QuickBooks (billing and accounting)
Email (ticketing)
Webhooks (custom integrations)

For each integration you used in ConnectWise:

Check if Aerie supports it natively.
If yes: configure it in Aerie. If no: use Zapier or a webhook.
Test the integration.

Example: If you used Zapier to sync ConnectWise tickets to Slack, reconfigure that Zapier flow to use Aerie instead.

3.4 Train Your Team

Before cutover:

Administrators: Full Aerie training (settings, permissions, workflows, reporting)
Technicians: Ticket management, time tracking, asset management, client communication
Managers: Dashboard, reporting, forecasting, team performance metrics
Finance: Invoicing, project costing, profitability analysis

Budget 4–8 hours of training per role. Aerie provides video training, live webinars, and documentation.

Phase 4: Parallel Running (Weeks 5–7)

4.1 Run Both Systems Simultaneously

For 2–4 weeks, your team will use Aerie while maintaining ConnectWise as backup:

Do this:

Log all new tickets in Aerie (not ConnectWise)
Close all tickets in Aerie (mirroring the final status from ConnectWise)
Track time and expenses in Aerie
Generate quotes and invoices from Aerie
Use Aerie's RMM (deploy Aerie agents to client machines)

Don't do this:

Create tickets in both systems (data duplication nightmare)
Use ConnectWise RMM (switch to Aerie RMM; don't run both)
Use ConnectWise for new quotes or invoices

4.2 Validate Data Completeness

Weekly, run these checks:

Ticket count: Total tickets in Aerie ≈ historical tickets in ConnectWise? (Should match.)
Client list: All clients in Aerie? Any missing?
Contracts: All active contracts present?
Assets: Major assets present? (You may not need every asset—that's OK.)
Financial data: Invoices reconcile with ConnectWise?

If anything is missing, investigate and correct during parallel running (before cutover).

4.3 Gather Feedback from Your Team

During parallel running, your team will find issues:

"How do I do X in Aerie?" → Documentation or training gap
"This field is in the wrong place." → UI preference (usually minor)
"This workflow isn't working." → Configuration issue

Document feedback weekly. Address critical issues immediately. Address nice-to-haves post-cutover.

Phase 5: Cutover (Week 8)

5.1 Plan Your Cutover Day

Choose a slow day (Tuesday–Thursday, not Monday or Friday). Avoid month-end or year-end.

Cutover timeline (example: Tuesday, 9am–5pm):

Time	Task	Owner
9:00am	Announce cutover to team and clients	Manager
9:15am	Stop all ConnectWise RMM agents	Tech Lead
9:30am	Final data validation in Aerie	Tech Lead
10:00am	Deploy Aerie RMM agents to critical clients	Tech Team (phased)
12:00pm	Confirm no new tickets in ConnectWise	Manager
1:00pm	Update DNS/links to Aerie portal	Tech Lead
2:00pm	Send team welcome email (Aerie access links)	Manager
3:00pm	Go live: Team starts using Aerie exclusively	All
5:00pm	Final validation, close open issues	Manager

5.2 Final Validation Checklist

Before declaring cutover complete:

✅ All team members can log into Aerie
✅ All critical clients are visible in Aerie
✅ RMM agents are deployed and reporting
✅ Incoming emails are creating Aerie tickets (not ConnectWise)
✅ Time tracking and expense reporting works
✅ Integrations (Slack, Zapier, etc.) are functioning
✅ Reporting and dashboards are accessible
✅ No critical bugs or access issues

If any item is not complete, delay cutover by 1–2 days. Don't rush this.

5.3 Communicate with Clients

Send a professional message to all clients:

Email template:

We're Moving to Aerie OS – Portal Access Update

Hi [Client Name],

We're migrating to Aerie OS, our unified business operations platform. This means:

Your portal: You can still access your ticket history and account at [Aerie portal URL]

No action needed: We've migrated all your data automatically

Support continues: Reach out to us the same way; your tickets will be faster

Questions? Reply to this email.

Best,
[Your MSP Name]

Phase 6: Post-Cutover Stabilisation (Weeks 9–12)

6.1 Monitor for Issues

In the first 2 weeks post-cutover, expect edge cases:

Common issues:

Old ConnectWise integrations still trying to connect (disable them)
Team members reverting to old habits (gently re-train)
Performance hiccup during RMM agent deployment (temporary)
Missing data from ConnectWise (usually found during detailed reconciliation)

Establish a daily standup for the first week:

15-minute team call each morning
Discuss blockers, questions, bugs
Escalate to Aerie Support if needed

6.2 Optimise and Tune

After the first week:

Review dashboard and reporting: Is your data represented correctly?
Audit workflows: Are automations firing as expected?
Check RMM coverage: Are all client machines reporting?
Validate billing integration: Do invoices calculate correctly?

Make small optimisations (custom fields, alert settings, permission adjustments). Document everything.

6.3 Offboard ConnectWise

Once you're stable on Aerie (typically 2–4 weeks post-cutover):

Export historical data from ConnectWise as backup (just in case)
Decommission RMM agents on all client machines
Cancel ConnectWise subscription (end of billing cycle to avoid pro-rata fees)
Cancel IT Glue/Hudu (Aerie Wiki replaces this)
Reconfigure or cancel external RMM, CRM, password manager subscriptions
Update your website, email signatures, client portals to point to Aerie

Common Gotchas and How to Avoid Them

1. Forgetting Custom Fields During Import

What happens: Custom fields don't migrate, and your team asks "where's the vendor field?" weeks later.

Prevention: Before import, create a detailed list of custom fields you actually use. Delete obsolete ones from ConnectWise first. Test custom field migration in your test import.

2. RMM Agent Deployment Chaos

What happens: You try to run ConnectWise RMM and Aerie RMM simultaneously. They conflict. Monitoring stops.

Prevention: Plan RMM agent replacement carefully. Deploy Aerie agents to a test group first (e.g., 5 clients). Verify they're reporting. Then roll out to all clients. Only then decommission ConnectWise RMM.

3. Incomplete Workflow Rebuilding

What happens: You rebuild 80% of your automations in Aerie, miss one critical workflow, and suddenly tickets aren't being routed to the right team.

Prevention: Create a spreadsheet of every ConnectWise automation. Rebuild each one in Aerie. Test with sample tickets. Have your team validate before cutover.

4. Data Quality Issues During Import

What happens: You import dirty data (duplicate clients, malformed phone numbers, broken relationships) and spend weeks cleaning it up post-cutover.

Prevention: Clean your ConnectWise data before export. Remove duplicates, standardise formats, delete orphaned records. Test import on a small sample first.

5. Team Resistance and Retraining

What happens: Your team defaults to "that's how we did it in ConnectWise" instead of learning Aerie's better way.

Prevention: Train early and thoroughly. Explain why Aerie's workflows are better (fewer clicks, less manual work, AI-powered). Make the change feel positive, not painful. Pair experienced team members with less experienced ones during parallel running.

6. Forgetting to Update Client-Facing Links

What happens: Your website, email signatures, and client invoices still point to the ConnectWise portal. Clients are confused.

Prevention: Before cutover, audit everywhere you reference ConnectWise. Update links to Aerie. Send a client communication announcing the change.

Post-Migration Checklist

Once you're live on Aerie, work through this checklist:

Week 1 Post-Cutover

✅ Team is logging tickets exclusively in Aerie
✅ RMM agents deployed to 80%+ of clients
✅ Incoming email is creating Aerie tickets
✅ No critical bugs or access issues
✅ Daily standups happening

Week 2–3 Post-Cutover

✅ RMM agents deployed to 100% of clients
✅ Time tracking and expense reporting validated
✅ Invoicing and billing reconciled with ConnectWise
✅ Dashboards and reports showing correct data
✅ All integrations (Slack, Zapier, etc.) functional

Week 4+ Post-Cutover

✅ Team is fully comfortable with Aerie workflows
✅ No lingering ConnectWise questions or edge cases
✅ Historical data archived and backed up
✅ ConnectWise and legacy tools fully decommissioned
✅ Custom workflows optimised and validated
✅ New features (CRM, advanced automation, security modules) explored and adopted

Questions? Support Resources

Aerie Migration Support:

Live migration guide available at [Aerie docs URL]
Schedule a migration consultation: hello@aerie-tech.co.uk
Migration FAQ: [Aerie help portal]

Your team:

Designate one person as "Aerie champion"—they're the expert
Have them attend Aerie training first, then train others
Create an internal Aerie troubleshooting channel (Slack/Teams)

Final Thoughts

Migration is an investment—in time, effort, and sometimes cost. But the payoff is significant: one unified platform, fewer vendors, less cost, and (most importantly) more time for your team to do higher-value work instead of manual ticket shuffling.

The migration timelines and gotchas in this guide are based on real MSP experiences. Your migration may vary depending on data complexity, team size, and integration dependencies. But now you know what to expect and how to plan.

Ready to make the move? Reach out to Aerie Support to start your migration conversation.