Jim leads the Directions on Microsoft editorial team and has been writing about technology since the early 1990s. Most recently he's covered Teams, Windows Server and related OSs, and enterprise IT infrastructure.
He brings with him over 15 years supporting and teaching academic and researching technology at large universities like University of Washington and The Ohio State University, a decade in operations management for a global engineering firm, and experience as technical producer of a live service game based on the popular Magic: The Gathering property.
Jim holds a B.A. with graduate studies in philosophy and a minor in computer science from The Ohio State University.
Latest Content by Jim Gaynor
Roadmap
Updated: July 25, 2025 · by Multiple Authors
Places Roadmap
Microsoft Places is a set of advanced work-scheduling features for Teams and Exchange Online, intended for employees who move frequently...
In Brief
Updated: July 20, 2025 · by Jim Gaynor
Skype for Business Server SE Is Generally Available
Skype for Business Server SE is generally available; customers have until Oct. 14, 2025, to upgrade before support ends for...
Roadmap
July 17, 2025 · by Multiple Authors
Application Platforms Roadmap
Describes the components and services available in Azure and on-premises for creating and deploying applications.
Blog
July 16, 2025 · by Multiple Authors
Exchange, Skype Servers Get Barely Extended Security Updates
Just-announced (and unexpected) Extended Security Update programs will give qualifying customers who need more time to migrate to Exchange Server...
Analyst Report
July 8, 2025 · by Jim Gaynor
Windows Server 2025 Hotpatching Available as a Subscription
Windows Server 2025 hotpatching, which enables security update patches without reboots for all editions of Windows Server 2025, is generally...
Analyst Report
June 9, 2025 · by Jim Gaynor
Project for the Web Transitioning to Planner in August
The Project for the Web stand-alone service will be retired starting Aug. 2025, finalizing a transition to Planner that began...
Roadmap
Updated: May 28, 2025 · by Jim Gaynor
Planner Roadmap
Microsoft Planner is a Microsoft-hosted work management tool that includes basic task and project management capabilities and premium project management...
Analyst Report
May 17, 2025 · by Jim Gaynor
Teams App Management Migrates to App-Centric
App-centric management for Teams apps, which replaces the permission policy-based model with a more direct approach to managing app availability,...
Roadmap
Updated: April 21, 2025 · by Multiple Authors
Server Application Version Support
Chart shows several server application versions and their eligibility for Microsoft product support on recent versions of Windows Server and...
Roadmap
Updated: April 18, 2025 · by Multiple Authors
To Do Roadmap
Roadmap for To Do, a Microsoft-hosted, personal task management application, available in most Office 365 plans.