Businesses across the Caribbean can now integrate voice calling directly into Microsoft Teams, thanks to a new partnership between cloud communications provider LoopUp and regional telecom Digicel. The collaboration delivers the first Microsoft-certified Operator Connect service in the region, eliminating the need for on-premises telephony hardware.

What just happened

LoopUp and Digicel Business have jointly launched a managed service that lets organizations add PSTN calling to Microsoft Teams using the Operator Connect program. The service, now generally available, allows enterprises to obtain phone numbers from Digicel—a wireless and broadband provider with deep roots in the Caribbean—and assign them to users directly from the Teams admin center.

Operator Connect is a Microsoft program that lets certified operators provision and manage phone numbers natively within the Teams platform. Instead of deploying session border controllers (SBCs) or maintaining complex Direct Routing configurations, IT admins can click through a simple portal to connect numbers from a participating carrier. LoopUp acts as the service integrator, handling the technical interconnection between Digicel’s network and Microsoft’s cloud, while Digicel provides the PSTN connectivity and local number inventory.

No launch date was specified in the joint announcement, but the companies confirmed the service is live for new and existing Digicel business customers in 25 Caribbean markets, including Jamaica, Trinidad and Tobago, Barbados, and others. Pricing was not disclosed; enterprises are encouraged to contact Digicel directly for quotes.

What it means for you

For IT decision-makers and Teams administrators in Caribbean organizations, this is a significant leap. Until now, adding external calling to Teams in the region usually meant either adopting Microsoft Calling Plans—which have limited geographic availability and may not offer local numbers—or implementing Direct Routing, which requires purchasing, configuring, and maintaining hardware. Operator Connect with Digicel removes that complexity.

For administrators

  • Simplified setup: From the Teams admin center, navigate to Voice > Operator Connect. Once your tenant is authorized, Digicel numbers appear as a selectable option. Assign them to users with a few clicks—no PowerShell scripting or SIP configuration needed.
  • Centralized management: Number inventory, user assignments, and emergency location mapping all live inside the familiar Teams portal. No separate carrier portals to learn.
  • Local support: Digicel’s regional presence means you deal with a provider that understands local regulatory requirements, number porting, and support hours.
  • License requirements: Users still need a Teams Phone license (available standalone or as part of Microsoft 365 E5) and an appropriate Operator Connect calling plan from Digicel. Existing Direct Routing or Calling Plan users can migrate with proper planning.

For end users

Employees notice nothing but a seamless calling experience. The Teams desktop or mobile app gains a dial pad; incoming and outgoing calls use the assigned Digicel number. Features like hold, transfer, voicemail, and call recording work as expected. Call quality benefits from Digicel’s local network peering with Microsoft’s datacenters—latency stays low within the Caribbean.

What’s missing

  • Emergency calling: Operators must support dynamic emergency calling in the Teams admin center. The announcement didn’t detail Digicel’s E911 capabilities, so confirm during procurement.
  • Number porting: Porting existing numbers is often a manual process; check with Digicel whether your current numbers can be transferred and how long it takes.
  • Global reach: While ideal for Caribbean-based business, companies with large international workforces may still need a mix of Operator Connect partners or Calling Plan add-ons for other regions.

How we got here

Microsoft has steadily expanded Teams telephony since replacing Skype for Business Online. The 2021 launch of Operator Connect added a middle ground between fully Microsoft-managed Calling Plans and the do-it-yourself Direct Routing model. It promised faster deployment, fewer hardware hops, and more operator choice.

But adoption in smaller regions lagged. The Caribbean, with its fragmented telecom market and cross-island regulatory hurdles, saw no certified operators. Enterprises either relied on legacy PBXs or jury-rigged Direct Routing through third-party SBC providers. Larger regional carriers like Digicel already offered voice services, but integration with Teams required custom engineering—until LoopUp stepped in.

LoopUp has been a Microsoft voice partner since 2020, already operating Operator Connect in the UK and Europe. The company’s platform abstracts the complex telephony protocols and gateways, letting carriers like Digicel plug in quickly. For Digicel, the partnership is a logical extension of its “Digicel Business” portfolio, which already provides cloud, security, and managed IT services to enterprises.

What to do now

If your organization wants to move its voice workloads to Teams via Digicel, here’s a practical checklist:

  1. Verify licensing: Ensure users who need calling have a Teams Phone license assigned. Confirm your Microsoft 365 tenant is in a supported region (the Americas tenant should work).
  2. Contact Digicel Business: Reach out via the Digicel Business website or your account manager. Inquire about Operator Connect availability, number availability in your specific country, pricing, and any minimum commitments.
  3. Prepare your tenant: In the Teams admin center, go to Voice > Operator Connect. Add Digicel as an operator. This may require Digicel to provide an authorization code or to whitelist your tenant.
  4. Plan number assignments: Decide whether you’ll acquire new local numbers or port existing ones. If porting, gather recent bills and account information from your current telephony provider.
  5. Update emergency locations: For each user or network location, define emergency addresses in the Teams admin center. This is critical for dynamic E911, and Digicel will need to map these to the correct public safety answering point.
  6. Pilot with a small group: Test with a handful of users before a company-wide rollout. Check call quality, inbound/outbound dialing, and voicemail routing.
  7. Train end users: While the Teams dial pad is intuitive, communicate the change. Let employees know their new number, how to set up voicemail, and how to use the Teams mobile app for calls.

Administrators already using Direct Routing can evaluate whether to switch. Operator Connect typically reduces operational overhead, but you’ll lose some low-level control over call routing and SBC redundancy. Weigh the cost savings against any custom integrations you currently rely on.

Outlook

This partnership signals growing maturity for Teams as a global business phone system. Microsoft has stated its ambition to make Operator Connect the default choice for enterprises, and every new carrier expands that vision. LoopUp’s role as an aggregator suggests it may replicate this model in other underserved regions—Africa, parts of Asia, or the Pacific Islands.

Digicel gains a sticky business service that deepens its enterprise relationships beyond connectivity. Expect bundled offers that combine Teams Phone with Digicel’s broadband and mobile plans. Whether other Caribbean operators, like Flow or regional incumbents, follow suit with their own Operator Connect certifications remains an open question. For now, Digicel and LoopUp have a first-mover advantage, and Caribbean businesses have a viable, cloud-native alternative to creaky PBXs.