ConnectWise Integration – Frequently Asked Questions

Applies To: Work 365 (Dynamics 365 / Power Platform)
Audience: Billing Teams, System Administrators, Integration Specialists

Overview

The Work 365–ConnectWise (CW) integration automates the push of customers, agreements, products, and billing data from Work 365 → ConnectWise PSA. This FAQ explains key behaviors, setup expectations, and best practices so your PSA stays aligned with your subscription source of truth.

Reference: Work 365 Documentation – ConnectWise Integration Guide

Prerequisites (at a glance)

• ConnectWise PSA: API Member (or API-only user), Public/Private API keys, security role with Agreement/Finance API permissions, correct Company and Site configuration.

• Work 365: System Administrator (or Work 365 Admin) rights; products and price lists configured; accounts have Primary Contact.

• Network/Security: Allow outbound HTTPS to CW API endpoint; keep keys secret; store per your security policy.

• Environment: Validate in sandbox first; document mappings and test cases.

Frequently Asked Questions

1) Is the integration a one-way sync?

Yes. Work 365 is the system of record. Data flows Work 365 → ConnectWise.
Updates you make directly in ConnectWise do not flow back and can be overwritten on the next push.
Action: Perform all license/subscription updates in Work 365.

See also: Work 365 Support – ConnectWise Integration Overview

2) Why should I avoid annual agreements in ConnectWise?

Annual CW agreements can defer mid-cycle changes (adds/removes/price updates) until term-end, creating billing gaps.
Best practice: Use Monthly (or one-time) agreements so mid-cycle changes appear on the next CW invoice and align with Work 365 cycles.

See also: Work 365 Support – Billing & CW Synchronization

3) Why must customers have a Primary Contact in Work 365 before syncing?

CW requires a Contact on each Company. If a Primary Contact is missing in Work 365, the agreement sync fails.
Before syncing:

• Ensure each Account has a Primary Contact (valid email/phone).

• Recommended sequence: Products → Customers → Agreements → Changes.

See also: Work 365 Support – Syncing Agreements to ConnectWise

4) How often should I push to ConnectWise?

Align frequency with change volume and billing cadence:

Tip: Establish a recurring review to confirm:

• All new/updated agreements synced successfully

• Mid-cycle price/seat changes are reflected

• No errors in Integration Jobs / Work 365 Logs

5) What objects/fields are typically synchronized?

• Companies (Accounts) → ConnectWise Companies

• Products (SKUs) → CW Catalog Items (name/SKU, UOM, price)

• Agreements → CW Agreements (type, billing cycle, start/end, recurring amounts)

• Quantity/Price Changes → Agreement additions/adjustments

• Usage/NRIs (optional) → Separate CW lines/agreements (recommended split)

Exact field mapping can be customized; ensure UOM, Agreement Type, Revenue/GL and Tax mappings are defined on the Work 365 side.

6) Will mid-cycle changes appear automatically on the next CW invoice?

Yes—if the CW agreement is Monthly (or configured to allow in-cycle updates).
For Annual CW agreements, updates may be deferred to renewal, which is why we recommend monthly.

7) How do discounts and taxes work between systems?

• Discounts: Prefer percentage/line-level discounts in Work 365; map to CW additions accordingly. Flat credits often work best as NRIs (one-time lines).

• Taxes: CW and Work 365 can calculate taxes independently. Ensure your tax jurisdiction/rate mapping is consistent to avoid double/under-taxing.

8) Does Work 365 send invoices to ConnectWise?

No. The integration does not push Dynamics/Work 365 invoice documents into CW. It pushes agreement/products/quantities/prices so that CW invoicing can run accurately. Reconciliation is performed by comparing Work 365 invoices to CW agreement invoicing.

9) How do I handle NRIs and Azure usage in CW?

• Keep NRIs (one-time charges) on separate CW agreements (or distinct addition types) for clarity.

• Azure usage is best on a dedicated monthly agreement to match your “bill in arrears” policy.

10) What about multi-currency and multiple CW companies?

• Multi-currency: Ensure the CW company/board supports your billing currency; Work 365 pushes values in the contract’s currency.

• Multiple CW companies: You can target specific CW companies/regions via mapping; keep processor/company/board mappings clear in your runbook.

11) How are rounding differences handled?

Minor differences can occur due to CW rounding rules. Standardize decimal precision (price and quantity) and reconcile monthly; adjust mapping if needed.

12) How are errors surfaced and retried?

Check Work 365 → Integration Jobs / Logs. Common responses:

• 401/403 Unauthorized/Forbidden → Check API keys/permissions

• 404 Not found → Mapping target (company/product/agreement) missing

• 409 Conflict/Duplicate → Existing record with same key; adjust mapping
  Fix the root cause and re-run the job (or push on next scheduled run).

Setup Checklist (Quick Reference)

• ✅ Map Products/SKUs in Work 365 to CW Catalog Items (UOM, revenue types).

• ✅ Ensure every Customer has a Primary Contact.

• ✅ Define Agreement mappings (type, cycle, board) that match Work 365 billing.

• ✅ Decide sync cadence and owners (who runs it, when, how validation is done).

• ✅ Test in sandbox, reconcile test output, then promote to production.

Best Practices

• Source of truth: Make all subscription/price/seat changes in Work 365, not CW.

• Avoid annual CW agreements: Use Monthly to respect mid-cycle changes.

• Separate contracts: Split license vs. usage (and NRIs) into distinct CW agreements.

• Reconcile regularly: Compare Work 365 invoices vs CW agreement invoices monthly.

• Document the process: Cadence, roles, exception handling, validation steps.

Troubleshooting Tips

• Agreement didn’t appear in CW: Check Primary Contact, agreement mapping, and the latest Integration Job result.

• Values in CW look outdated: A change may not have been pushed yet—run the next sync and re-check logs.

• Mid-cycle updates missing on invoice: Ensure the CW agreement isn’t Annual; switch to Monthly and re-push changes.

• Auth errors (401/403): Rotate or re-enter API keys, confirm API member permissions.

• Duplicate item (409): Harmonize product keys/SKUs; clear duplicates in CW or adjust mapping keys.

Summary

The Work 365 → ConnectWise integration is one-way and designed to keep PSA billing aligned with your subscription source of truth. Keep Primary Contacts current, avoid annual CW agreements, maintain clear mappings, and run a consistent sync/review cadence. You’ll get accurate, timely billing in CW with fewer corrections.