Managed IT services

Microsoft support deadlines in 2026–2027 that SMBs should plan for now

By the Montreal IT team

Microsoft support deadlines often arrive in groups.

A business may have replaced some Windows 10 PCs while still running a 2016 server, an application on SQL Server 2016 and Office 2021 on several workstations. Each product has its own date, options and dependencies.

These are the most useful deadlines for an SMB to review in 2026–2027.

SQL Server 2016 — extended support ended July 14, 2026

SQL Server 2016 has already reached the end of extended support.

Databases may continue running, but the organization now needs a deliberate choice between:

  • migration to a supported release;
  • application modernization or replacement;
  • Extended Security Updates as a temporary bridge when eligible;
  • retirement of the workload.

The first task is identifying which applications actually use SQL Server 2016. See our guide: SQL Server 2016 is out of support.

Office LTSC 2021 and Office 2021 — October 13, 2026

Office LTSC 2021 and Office 2021 reach end of support on October 13, 2026.

After that date, Microsoft will no longer provide the normal security updates, fixes and support associated with those products.

The inventory should check:

  • Office LTSC 2021, Office 2021, Office 2019 and Office 2016;
  • Outlook and Excel add-ins;
  • macros;
  • PST files;
  • activation and licence type;
  • Microsoft 365 compatibility;
  • installations on shared or rarely used PCs.

Common options are Microsoft 365 Apps or Office LTSC 2024 for organizations that still require a supported perpetual release.

Windows 10 Enterprise 2016 LTSB — October 13, 2026

Standard Windows 10 22H2 reached end of support on October 14, 2025, but some LTSC and LTSB editions follow different schedules.

Windows 10 Enterprise 2016 LTSB reaches the end of extended support on October 13, 2026.

These systems are often found on:

  • specialized equipment;
  • industrial devices;
  • kiosks;
  • rarely changed workstations;
  • older applications.

Confirm the exact edition before deciding. Our guide Windows 10 after end of support explains how to choose between upgrade, replacement and ESU.

Windows Server 2012 and 2012 R2 — ESU Year 3 ends October 13, 2026

Normal extended support for Windows Server 2012 and 2012 R2 ended in 2023. Organizations using Extended Security Updates reach the end of Year 3 on October 13, 2026.

Any active 2012/R2 server should be treated as an immediate priority. Check:

  • Windows roles;
  • applications and databases;
  • backups and restore tests;
  • migration options;
  • temporary risk-reduction controls;
  • ownership and retirement date.

Windows Server 2016 — January 12, 2027

Windows Server 2016 extended support ends on January 12, 2027.

This often affects:

  • domain controllers;
  • file servers;
  • line-of-business applications;
  • print servers;
  • databases;
  • virtual machines installed with older software.

Migration usually takes longer than expected because dependencies are poorly documented. See our guide: Windows Server 2016 support ends in January 2027.

Products already out of support

Some important deadlines have already passed:

  • Windows 10 22H2 — October 14, 2025;
  • Office 2016 and Office 2019 — October 14, 2025;
  • Exchange Server 2016 and 2019 — October 14, 2025.

Software that still runs is not necessarily software that is still supported.

Turn dates into an actual plan

A list of deadlines is not enough. For each product, record:

  • number of affected devices or servers;
  • dependent applications;
  • business owner;
  • backup method;
  • most recent restore test;
  • intended destination;
  • vendor compatibility;
  • maintenance window;
  • budget or licensing model;
  • target date;
  • documented exceptions.

Priority should follow actual risk, not only calendar order. An Internet-exposed server or an application without tested backups may be more urgent than an isolated workstation whose replacement is already ordered.

A simple lifecycle review

A managed IT environment review can combine these deadlines into one plan covering workstations, servers, applications, data, backups and licences.

The useful output is not a long report. It is a clear list of:

  • what to replace;
  • what to upgrade;
  • what to retire;
  • what to protect temporarily;
  • in what order;
  • with which dependencies and decisions.

Contact Montreal IT to define a focused inventory.

Keep exploring