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Microsoft ended extended support for Exchange Server 2016, Exchange Server 2019, Skype for Business Server 2015, and Skype for Business Server 2019 in October 2025. The end of support means these installations no longer receive Microsoft security updates, non-security updates, bug fixes, or technical support. Organizations still running them must choose a supported replacement: cloud services such as Exchange Online and Microsoft Teams, or the newer Subscription Edition products for on-premises deployments.
Which products are no longer supported?
Microsoft’s customer-facing notice dates the end of support to October 14, 2025. Individual Microsoft lifecycle tables show October 15, 2025 in Pacific Time, reflecting the same deadline across time-zone displays.
| Product | Mainstream support ended | Extended support ended |
|---|---|---|
| Exchange Server 2019 | January 10, 2024 | October 15, 2025 in the lifecycle table |
| Exchange Server 2016 | Not separately stated in the cited roadmap | October 14, 2025 in Microsoft’s roadmap |
| Skype for Business Server 2019 | January 10, 2024 | October 15, 2025 in the lifecycle table |
| Skype for Business Server 2015 | October 14, 2020 | October 15, 2025 in the lifecycle table |
Skype for Business Server LTSC 2021 is separate and is scheduled to remain supported until October 13, 2026.
What end of support means for an existing server
An unsupported server may continue running, but Microsoft no longer commits to maintaining it. After the October 2025 deadline, Microsoft says the affected Exchange releases no longer receive security updates, non-security updates, stability or usability bug fixes, or technical support. The same end-of-support principle applies to the listed Skype for Business Server releases.
#1 Best Overall
- 64 bit | 1 Server with 16 or less processor cores | provides 2 VMs
- For physical or minimally virtualized environments
- Requires Windows Server 2025 User and/or Device Client Access Licenses (CALs) | No CALs are included
- Core-based licensing | Additional license packs required for servers with more than 16 processor cores or to add VMs | 2 VMs whenever all processor cores are licensed.
- Product ships in plain envelope | Activation key is located under scratch-off area on label |Beware of counterfeits | Genuine Windows Server software is branded by Microsoft only.
- Newly discovered vulnerabilities will not receive normal Microsoft security fixes for these releases.
- Product defects and reliability problems are no longer covered by routine bug-fix support.
- Microsoft support cannot provide normal troubleshooting or remediation for the retired versions.
- Keeping the software online does not extend its lifecycle or restore support eligibility.
Organizations should treat continued operation as a temporary risk decision, not as a supported long-term strategy. Security controls such as network isolation, monitoring, access restrictions, and a documented incident plan can reduce exposure while a migration is being completed, but they do not replace vendor security updates.
Supported replacement paths for Exchange
Exchange Online through Microsoft 365
Microsoft recommends Microsoft 365 or Exchange Online for organizations moving away from legacy Exchange Server. Mailboxes, identity, compliance configuration, applications, and mail flow still require planning, but the service provider operates the underlying Exchange infrastructure and its update process. This route can reduce server hardware, patching, and data-center responsibilities.
Rank #2
- Offers quick and easy installation on PC
- The software is licensed for 5 User CAL
Exchange Server Subscription Edition
Exchange Server Subscription Edition became available on July 1, 2025 and is supported under Microsoft’s Modern Lifecycle Policy. It is the on-premises option for organizations that need to retain local control or cannot move all workloads to the cloud. Microsoft’s additional-support policy says Exchange Server Subscription Edition will not reach end of support before December 31, 2035, although lifecycle dates and supported versions can change under that policy.
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Supported replacement paths for Skype for Business
Microsoft Teams
Microsoft recommends migrating Skype for Business Server users to Microsoft Teams for cloud collaboration, meetings, messaging, and calling. A Teams transition should account for identity, telephony, meeting-room devices, federation, compliance, recording, and user training rather than treating it as a simple client installation.
Rank #3
- Server 2022 Standard 16 Core
Skype for Business Server Subscription Edition
Skype for Business Server Subscription Edition also began on July 1, 2025 and remains an on-premises supported path. Microsoft’s additional-support policy says it will not reach end of support before December 31, 2035, subject to the Modern Lifecycle Policy. This option preserves a server-based architecture for organizations with regulatory, connectivity, integration, or operational reasons to keep communications on premises.
Cloud or on premises: how to decide
| Decision factor | Cloud services | Subscription Edition on premises |
|---|---|---|
| Infrastructure control | Microsoft operates the service platform; the organization configures tenants and policies. | The organization controls servers, networks, storage, and deployment. |
| Operations and patching | Less server maintenance, with service changes managed by Microsoft. | The organization remains responsible for capacity, availability, upgrades, and operational procedures. |
| Data residency and regulation | Must be assessed against Microsoft 365 or Teams region, service, and compliance capabilities. | May offer more direct control over where systems and data are hosted, subject to the organization’s own controls. |
| Migration complexity | Requires tenant, identity, mail-flow, collaboration, and application planning. | Requires a supported server deployment, coexistence planning, and an ongoing lifecycle program. |
| Cost model | Typically recurring service subscriptions and migration work. | Subscription licensing plus hardware, facilities, administration, and support costs. |
| Future lifecycle burden | Fewer server-version projects, but service and licensing changes still need governance. | More infrastructure control, with another server lifecycle to operate and renew. |
A practical migration sequence
- Inventory dependencies: record Exchange databases, mail-flow connectors, relay applications, archives, compliance tools, identity systems, Skype voice routes, meeting rooms, integrations, and custom scripts.
- Classify constraints: document regulatory or data-residency requirements, offline or network limitations, integration dependencies, and the organization’s tolerance for operating another server platform.
- Select the target: compare Exchange Online with Exchange Server Subscription Edition, and Microsoft Teams with Skype for Business Server Subscription Edition.
- Build a coexistence plan: define identity synchronization, DNS and mail routing, federation, telephony, client readiness, pilot groups, rollback conditions, and communications.
- Migrate in waves: start with a controlled pilot, validate mail flow and collaboration features, then move departments in measured batches.
- Retire legacy systems: remove unsupported servers only after mail routing, archives, applications, voice services, records retention, and monitoring have been verified on the target platform.
What organizations should do now
If Exchange Server 2016 or 2019, or Skype for Business Server 2015 or 2019, is still deployed, begin a formally owned migration or replacement project immediately. Microsoft explicitly advises customers who have not migrated from Exchange Server 2016 or 2019 to Microsoft 365, Office 365, or Exchange Server Subscription Edition to start planning. Skype customers should make the equivalent Teams-versus-Subscription-Edition decision, while separately tracking the October 13, 2026 deadline for Skype for Business Server LTSC 2021.
Quick Recap
Best Value
- Unlock all the features by installing this product on PC
- The software is licensed for 1 User CAL
Rank #4
- 64 bit | 1 Server with 24 or less processor cores | provides 2 VMs
- For physical or minimally virtualized environments
- Requires Windows Server 2025 User and/or Device Client Access Licenses (CALs) | No CALs are included
- Core-based licensing | Additional license packs required for servers with more than 16 processor cores or to add VMs | 2 VMs whenever all processor cores are licensed.
- Product ships in plain envelope | Activation key is located under scratch-off area on label |Beware of counterfeits | Genuine Windows Server software is branded by Microsoft only.
Product prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on Amazon at the time of purchase will apply.
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