Sync 365 vs CloudOlive
Choose CloudOlive to reconcile supplier invoices across the stack. Choose Sync 365 when Microsoft and Entra data should continuously determine the recurring quantities sent to your PSA.
What Sync 365 does differently
A licence count is only the starting point. Sync 365 maps new subscriptions, builds the quantities your MSP sells, and routes each result to the right supported PSA record.
Major differentiator
Set the licence, commitment-term, billing-profile and PSA destination rules once. When matching subscriptions appear, AutoMap can apply those rules automatically or queue them for approval.
Custom licences
Create the active-user or managed-user count your MSP actually sells, then use it across related support, backup, security and filtering lines in the PSA.
Explore custom licence billing
Calculated custom licences
Add and subtract Microsoft licences, subscriptions, users, custom licences or fixed quantities to model bundles, included seats and overages before the result reaches the PSA.
Explore calculated billing
Filters and split billing
Split one Microsoft tenant into separate billable populations using office, city, state, country, department, company, domain, Entra ID group or custom attributes.
Explore filters and split billingAt a glance
Compare the jobs that determine billing accuracy: new-subscription mapping, custom and calculated quantities, split-tenant rules, Azure controls, and ownership of the final PSA record.
| What matters | Automates repeat billing workSync 365 | CloudOlive | Why it matters |
|---|---|---|---|
| Primary billing job | Microsoft billing automationA focused Microsoft billing layer for licences, Azure, managed users, contacts, and custom recurring services while the supported PSA remains the invoicing system of record.[6][2][5] | Vendor reconciliation controlCloudOlive: Vendor-wide invoice and PSA-contract reconciliation, anomaly detection, and management review.[7][9] | Start with the operational problem each product is designed to own before comparing individual features. |
| Source-data collection | Connected Microsoft dataSync 365 starts from connected Microsoft and Entra data used by its licence, Azure, filtering, custom, and calculated-quantity workflows.[1][5][2][3][4] | Mixed-source data ingestionCloudOlive documents a mixed collection model using APIs, CSVs, vendor portals, and guided uploads. For file-based suppliers, the team must obtain and load the current invoice or usage data before reconciliation can begin.[10] | Reconciliation can automate the comparison after ingestion while still leaving a recurring collection and upload task for sources that do not connect directly. |
| New subscription mapping | Reusable subscription rulesAutoMap applies reusable Microsoft licence and commitment-term rules to matching new subscriptions, routing each to the configured billing profile and PSA destination automatically or pending review.[1] | Supplier-to-contract mappingCloudOlive ingests supplier data and maps it against client contracts. Its reviewed public material emphasises controlled reconciliation rather than reusable Microsoft commitment-term rules for matching new subscriptions.[7][8] | A reusable mapping rule reduces the chance that a newly appearing subscription waits for another manual setup step before billing cutoff. |
| Custom recurring services | User-driven service billingA configured Microsoft or managed-user count can keep support, backup, antivirus, security, filtering, and other related recurring PSA lines aligned.[2] | Bundle reconciliationCloudOlive documents bundles and multi-tenancy reconciliation across supplier and PSA data. Sync 365 should be compared when a Microsoft or active-user count must drive several non-vendor recurring lines.[7][8] | MSPs often sell a service bundle around each user, not only the underlying Microsoft licence. |
| Calculated quantities and overage | Calculated billing rulesCalculated custom licences add and subtract Microsoft licences, subscriptions, users, custom licences, or fixed values to produce bundles, included-seat deductions, and overage quantities.[3] | Invoice-to-contract comparisonCloudOlive focuses on comparing invoice and contract quantities. The reviewed public material does not describe a Microsoft/user expression builder that adds and subtracts counts for included seats, overage, or deduplication.[7][8] | The correct quantity may be a formula—such as protected mailboxes minus users already included in the bundle—not a copied vendor count. |
| Location, department, and split billing | Attribute-based split billingOffice, city, state, country, department, company, domain, Entra group, and custom attributes can split one tenant into separate billable populations and PSA records.[4] | Complex vendor mappingsCloudOlive supports complex vendor mappings and multi-tenancies. The reviewed material does not describe deriving PSA quantities directly from office, department, domain, Entra group, or custom user attributes.[7][8] | One Microsoft tenant can represent several sites, departments, franchises, cost centres, or legal billing entities. |
| Azure consumption workflow | Azure review and postingAzure consumption can move through billing profiles, markup, billing-period review, approval or configured auto-approval, and supported PSA posting.[5] | Invoice-led Azure controlCloudOlive can reconcile supplier data across the vendor stack; buyers should compare that invoice-led control with Sync 365’s Microsoft-to-PSA Azure consumption, markup, and approval workflow.[7] | Azure comparison should include data timing, markup, period review, approval, exception handling, and the final PSA record—not only ingestion. |
| PSA ownership and scope | Multi-PSA billing layerSync 365 supports ConnectWise Manage, Autotask PSA, and HaloPSA workflows while the PSA remains responsible for invoices.[6] | Operator-controlled reconciliationCloudOlive integrates with ConnectWise and Autotask as a broad reconciliation control layer and deliberately gives operators control over sensitive billing decisions.[9][8] | Clear system ownership prevents overlapping automations and keeps finance confident about which record becomes the invoice. |
Beyond one-to-one sync
Start with Microsoft, managed-user or recurring-service data. Apply the commercial rule. Keep the related PSA lines aligned without rebuilding the logic in a spreadsheet each month.
Billing sources
Sync 365 billing rules
Automated PSA billing
Workflow differences
These are the practical differences to test with your own customer data—not a generic feature-score exercise.
AutoMap is term-aware, destination-aware, and designed to keep applying the rule after initial setup.
With Sync 365
Configure monthly and annual Microsoft commitment-term defaults, the Sync 365 billing profile, the company or filter-group PSA destination, and automatic or pending approval. Matching new subscriptions can then follow that route.[1]
With CloudOlive
CloudOlive ingests supplier data and maps it against client contracts. Its reviewed public material emphasises controlled reconciliation rather than reusable Microsoft commitment-term rules for matching new subscriptions.[7][8]
Why it matters
The useful distinction is not whether a product can sync a count. It is whether new Microsoft subscriptions inherit the right commercial and PSA-routing decisions without rebuilding the mapping.
Turn the trusted user or licence count into the support, backup, security, and filtering lines the MSP actually sells.
With Sync 365
Custom licences can use managed users, filtered licences, minimums, exclusions, and customer rules. One configured count can drive several related recurring items through their billing profiles into supported PSA records.[2]
With CloudOlive
CloudOlive documents bundles and multi-tenancy reconciliation across supplier and PSA data. Sync 365 should be compared when a Microsoft or active-user count must drive several non-vendor recurring lines.[7][8]
Why it matters
A Microsoft seat count can be correct while the surrounding managed-service invoice is still wrong. Keeping related lines tied to one reviewed quantity reduces that drift.
Use ordered additions and deductions when the billable number does not exist in any single source system.
With Sync 365
Calculated custom licences can combine Microsoft licences, subscriptions, all users, custom licences, and fixed quantities. Rules can apply filters, configured duplicate removal, included-seat deductions, and a zero floor before mapping the result to the PSA.[3]
With CloudOlive
CloudOlive focuses on comparing invoice and contract quantities. The reviewed public material does not describe a Microsoft/user expression builder that adds and subtracts counts for included seats, overage, or deduplication.[7][8]
Why it matters
Finance gets an explainable recurring result for rules that otherwise tend to live in spreadsheet formulas, custom scripts, or month-end adjustments.
Keep one tenant while producing separate location, department, franchise, group, or entity-specific billing populations.
With Sync 365
Sync 365 can include or exclude users by Microsoft and Entra attributes, map each filtered population to the relevant PSA record, and use a separate AutoMap destination for each filter group.[4][1]
With CloudOlive
CloudOlive supports complex vendor mappings and multi-tenancies. The reviewed material does not describe deriving PSA quantities directly from office, department, domain, Entra group, or custom user attributes.[7][8]
Why it matters
The tenant-wide total is often wrong for a multi-site or multi-entity agreement. Billing populations should reflect the customer structure that finance actually invoices.
Built around real MSP billing
Sync 365 customer stories show custom recurring rules and split-tenant billing working in live MSP operations.
Custom recurring billing
“Everyone can do 365 licensing. It’s the custom stuff I need.”
Chris F, Operations Director · Cleva Group
Read the Cleva Group storyOne tenant, many billing records
“There’s no way we would be able to service a customer like that manually.”
Sean Stuart, Operations Manager · IT Global
Read the IT Global storyCustomer-specific examples, not typical or guaranteed results.
Best fit
Choose around the system that should own the billing logic, the source data that determines quantity, and the amount of mapping or custom engineering your team wants to maintain.
Choose Sync 365 when
Sync 365 fits when Microsoft and Entra data must produce customer-specific recurring quantities and the MSP wants ConnectWise, Autotask, or HaloPSA to remain responsible for invoicing.[1][2][3][4][6]
Choose the alternative when
CloudOlive fits an MSP that wants to compare supplier invoices against PSA contracts across a wide vendor portfolio, keep finance in control of exceptions, and manage each supplier's documented ingestion route.[7][8][10]
Use a real customer in the demo
Use one real customer to compare Sync 365 with CloudOlive: a new annual Microsoft subscription, a managed-user bundle, an overage calculation, one filtered department or site, and the final PSA record. Follow every mapping, review, and exception step.
How Sync 365 fits
The PSA stays in control of invoicing. Sync 365 owns the reusable mapping, quantity and review logic that prepares supported billing records.
Bring Microsoft 365, Azure, managed-user and supported PSA data into one billing workflow.
Use AutoMap, billing profiles, minimums, exclusions, filters and calculated custom quantities.
Check pending mappings, calculated quantities, billing changes and configured Azure approvals.
Update supported PSA billing records while the PSA remains the invoicing system of record.
Frequently asked questions
CloudOlive is designed primarily for vendor-wide invoice and PSA-contract reconciliation, anomaly detection, and management review. Sync 365 focuses on turning Microsoft and Entra data into mapped, filtered, custom, or calculated quantities while a supported PSA remains the invoicing system of record.[1][2][3][4][6][7][9]
Not for every source. CloudOlive's own guide describes a mixed model in which vendor data may be gathered through APIs, CSVs, or portals, and its onboarding includes a guided upload process. For file-based suppliers, an operator must obtain and load the current invoice or usage data before CloudOlive can reconcile it; buyers should confirm the ingestion route and cadence for each supplier.[10]
In the public CloudOlive material reviewed, we did not find the same documented combination of Microsoft commitment-term rules, Sync 365 billing-profile routing, PSA destination routing, and per-company automatic or pending approval. That is a documentation comparison, not proof that an unpublished capability does not exist; verify it directly.[1][7][8]
Sync 365 provides custom and calculated licence workflows for managed-user services, minimums, filters, additions, deductions, bundles, and overage. CloudOlive should be tested with the same real customer rule so buyers can see where the source data, calculation, review, and PSA update live.[2][3][4][7][8]
CloudOlive and Sync 365 address different starting points: supplier invoices versus Microsoft and Entra billing data. Some MSPs may evaluate both layers rather than treat them as direct substitutes. Whichever design you choose, document the system of record and ensure two automations do not update the same customer quantity.[6][7][9]
Compare with your own billing data
Use one real Microsoft tenant, one new subscription, one custom quantity, and one PSA agreement to compare Sync 365 with CloudOlive. See the mapping, calculation, review, and update path end to end.
This buyer guide compares documented workflows rather than awarding a generic feature score. A capability not found in the public CloudOlive material reviewed is labelled as such, not presented as proof that no private or newer capability exists. Product information was reviewed on. Confirm plan, region, integration and workflow details with each vendor before buying.