This article is based on reporting originally published by TechTarget (techtarget.com) in September 2017. Quotes and examples are drawn from the original source.
The Windows DevOps Reputation Problem
Windows-based development shops have long carried a reputation for conservatism. Deeply entrenched legacy enterprise applications, vendor lock-in, and a cultural reluctance to adopt early software versions have historically slowed the adoption of DevOps practices in Microsoft-centric environments.
Critics argued that, for much of the mid-2010s, Microsoft lagged behind the open-source ecosystem — particularly in continuous deployment (CD) and application release automation. That gap, combined with the friction of integrating Microsoft tools with third-party platforms, kept many Windows shops from matching the deployment velocity of their Linux counterparts.
“Microsoft is making some inroads. They’re finally starting to open up compatibility with other things, but they’re years and years behind the ecosystem that’s developed in open source.”
Brandon Cipes, Managing Director of DevOps, cPrime
Third-Party Tools Bridge Windows DevOps Gaps
Rather than waiting for Microsoft to close the tooling gap, many Windows DevOps shops turned to third-party vendors to build functional — if sometimes fragile — automation pipelines. Tools such as TeamCity, Octopus Deploy, Electric Cloud’s ElectricFlow, and CA’s Automic gave early adopters a way to automate builds, tests, and deployments within a Windows-heavy environment.
These pipelines often involved multi-hop handoffs between Microsoft applications and third-party tools, introducing inefficiencies but enabling automation where none previously existed.
Case Study: Urban Science
Urban Science, a Detroit-based data analysis company focused on the automotive industry, adopted Electric Cloud’s ElectricFlow as its primary CI/CD orchestration platform. According to Marc Priolo, configuration manager at Urban Science, ElectricFlow managed DevOps workflows for approximately 80% of the company’s IT environment.
“Having the orchestration of ElectricFlow allows us to keep one perspective in mind when we’re creating a workflow — we try to use that as one tool to rule them all.”
Marc Priolo, Configuration Manager, Urban Science
The remaining 20% of workflows still relied on handoffs from Microsoft’s Team Foundation Server (TFS) to ElectricFlow. Priolo noted that fully consolidating into ElectricFlow would require developers to change how they interact with TFS — a change that had not been prioritised.
Case Study: NetEnt
NetEnt, an online gaming systems provider based in Sweden, took a production-first approach to automation. Rather than building a full pipeline from development through to production, the team deployed ElectricFlow specifically to manage and accelerate production deployments — then worked backwards toward earlier pipeline stages.
“We’ve tied in all components that are needed to create servers, deploying and upgrading our applications, to give us some more deployment speed and free us up to find other bottlenecks. We are looking to shift that left now, since the developers and testers have seen what we’ve done in production and they want the same kind of automation.”
Aloisio Rocha, Operations Specialist, NetEnt
NetEnt’s next step was to use ElectricFlow’s API integration with VMware to automate the creation and updating of SQL Server databases — a challenge common to Windows DevOps regardless of the underlying operating system. At the time of the original reporting, the team was using PowerShell scripts as an intermediary between ElectricFlow and VMware’s API, with plans to eliminate that middle layer.
The Island of Automation Problem
A recurring challenge in Windows DevOps environments is what practitioners call “islands of automation” — isolated pockets of automated workflow that cannot be connected to adjacent tools or older Microsoft software versions. When a single integration point fails or is unavailable, the entire pipeline efficiency drops sharply.
“If you can’t integrate one little bit of automation, it gets you just such a short bit of the way. A lot of people are trying to figure out how to deal with getting past that.”
Brandon Cipes, cPrime
This fragmentation was particularly acute when organisations ran older versions of Microsoft software that lacked REST API support or modern integration hooks. As Microsoft has updated its tooling, this barrier has gradually diminished.
Microsoft Products Recast the Windows DevOps Equation
By 2017, Microsoft had made meaningful improvements to its own DevOps product line. Newer versions of Team Foundation Server (TFS) and Visual Studio Team Services (VSTS) introduced tighter REST API integrations with third-party tools and expanded native DevOps capabilities — particularly around continuous delivery pipelines.
TFS 2017 and Release Pipelines
TFS 2015 was notably limited in release pipeline support — the feature did not arrive until Update 3. TFS 2017 addressed this more comprehensively, enabling teams to define full release pipelines with approval gates and role-based controls.
“We have a full release pipeline now, and we can set it up so that business analysts are the ones that dictate when things get pushed to production. We do hands-off deployments, and run three or four production deployments a day if we want to, without any issue.”
Anthony Terra III, Manager of Software Architecture and Development, Philadelphia-area law firm
Visual Studio Team Services (VSTS)
Visual Studio Team Services — the SaaS version of TFS, later rebranded as Azure DevOps — saw significant investment in CI/CD capabilities for Azure PaaS and IaaS environments. According to Sam Guckenheimer, product owner for VSTS at Microsoft at the time of the original reporting, a majority of VSTS users were deploying multiple times per day.
Updates in the six to twelve months preceding the original article added:
- Improved Git-based workflows for code review, testing, and quality assurance
- Kanban board support for DevOps team planning
- Higher-level dashboards for cross-team visibility into development status and assets
- Leaner Windows Server footprints better suited to containerised workloads
“There has been a lot of work in the most recent releases of Windows to make it leaner for server apps so that you could have a small footprint on your VM for Windows, and containerization is another step in that process.”
Sam Guckenheimer, Product Owner for VSTS, Microsoft
Where Windows DevOps Stood in 2017 — and What It Signals
As of the original reporting, Windows DevOps shops were making tangible progress. Third-party tools had proven capable of filling gaps that Microsoft’s own platform left open, while newer Microsoft releases were rapidly reducing those gaps. The combination of improved native tooling and a mature ecosystem of CI/CD integrations meant that Windows-centric organisations no longer needed to migrate to Linux-based stacks to achieve meaningful deployment automation.
Organisations still faced real friction: legacy application dependencies, reluctance to change established developer workflows, and integration challenges with older Microsoft software versions. But the direction of travel was clear — Microsoft was investing heavily in DevOps-first tooling, and Windows shops were beginning to reap the benefits.
Note: VSTS was subsequently rebranded as Azure DevOps in 2018, and Electric Cloud was later acquired and rebranded. TFS has been succeeded by Azure DevOps Server for on-premises deployments. Readers evaluating these tools today should consult current vendor documentation for up-to-date feature comparisons.