Schyler Ryan LinkedIn (opens in a new tab)
Cloud architecture & systems engineeringVermont · Remote

Schyler Ryan.

Senior Systems Engineer at Arrow Team

Cloud infrastructure.
The software behind it.

I design cloud and hybrid infrastructure and build the tools that support its deployment, security, and operation. My work spans networking, identity, certificate services, infrastructure automation, API integration, and software delivery, from architecture and implementation through troubleshooting and recovery.

Explore my expertise
01 /

Cloud architecture

AWS · Azure · Hybrid environments

02 /

Systems & security

Infrastructure · Networking · Identity

03 /

Software & integration

Operational tools · APIs · Delivery

01 / Architecture & expertise

AWS, Azure,
and hybrid infrastructure.

I approach architecture as a complete environment: where workloads run, how identities and networks connect, how changes are delivered, and how the system will be operated and recovered.

Public cloud

Amazon Web Services

Cloud architecture that considers workload, network, identity, and operational requirements together. I bring the same attention to dependencies, maintainability, and change control that I apply across the rest of the environment.

AWS · Architecture · System design

Public cloud

Microsoft Azure

Azure architecture, hub-and-spoke networking, VPN connectivity, and route analysis. Hands-on delivery includes Azure Virtual Desktop, Azure Files, FSLogix, and migrations to Azure platform-as-a-service solutions.

Azure networking · AVD · Azure PaaS

Hybrid & on-premises

Connected infrastructure

Cloud environments integrated with existing Windows, identity, virtualization, and network services. My work includes live server migrations, private-to-public-cloud moves, Hyper-V rebuilds, and the dependencies involved in keeping systems usable.

Windows · Virtualization · Migrations

What I work through in an architecture.

Workload placement & migration
Understand the application’s dependencies and choose an approach for hosting or migration, including the cutover, validation, and rollback plan.
Connectivity & identity
Work through routing, DNS, authentication, trust, and access requirements across cloud and on-premises services.
Repeatable implementation
Use PowerShell, Terraform, and engineering tools to make deployment, configuration, and validation consistent.
Operations & recovery
Consider performance, failure behavior, troubleshooting, and support handoff as part of the design.

Technical depth across the stack.

01

Infrastructure & virtualization

Server operations, domain-controller recovery, cluster troubleshooting, and the dependencies between compute, storage, and networking.

  • Windows Server
  • Hyper-V
  • VMware vSphere
  • Failover clustering
  • DFS / DFSR
02

Identity & access

Directory services, administrative access, multi-factor authentication, and recovery-aware policy design across connected environments.

  • Active Directory
  • Microsoft Entra ID
  • Duo MFA
  • YubiKey
  • Group Policy
03

Digital workspace & endpoints

Virtual desktop architecture, authentication, profile and storage integration, performance troubleshooting, and endpoint configuration.

  • Azure Virtual Desktop
  • FSLogix / Azure Files
  • Microsoft 365
  • Intune / Autopilot
04

Operational software & automation

Authenticated applications, background jobs, and onboarding workflows with managed identities, centralized credential handling, input validation, recovery procedures, and operator status reporting.

  • PowerShell / .NET
  • Terraform
  • Job orchestration
  • Service provisioning
  • Operator interfaces
05

PKI & certificate automation

Two-tier public key infrastructure, directory security hardening, and automation for certificate enrollment, renewal, trust installation, and endpoint deployment.

  • Certificate authorities
  • Certificate lifecycle
  • Endpoint integration
  • Trust troubleshooting
  • AD hardening
06

Networking & connectivity

Firewall and Layer 3 switching projects, SD-WAN integration, routing and traffic management, and cloud network path analysis.

  • Layer 3 switching
  • SD-WAN
  • Routing / QoS
  • Hub-and-spoke
  • Site-to-site VPN
07

API integration & software delivery

REST integrations with delegated authentication, permission enforcement, schema validation, and duplicate-operation safeguards. Repeatable delivery through automated checks, dependency validation, package signing, and controlled releases.

  • REST APIs
  • Delegated authentication
  • Git / GitHub
  • Package signing
  • Deployment verification
08

Security tooling & reporting

Automated assessments and endpoint reporting that consolidate findings into structured remediation reports, including identification of unauthorized remote-access software.

  • Assessment automation
  • Endpoint inventory
  • NinjaOne
  • Data processing
  • Remediation reporting

02 / Technical experience

From frontline support
to systems engineering.

Experience across cloud architecture, infrastructure delivery, operational software, security tooling, and senior technical escalations.

Software, security tooling & integration

Alongside infrastructure delivery, my professional engineering work includes:

Operational applications
Develop applications with authenticated interfaces, background-job orchestration, managed identities, centralized credential handling, and status reporting.
Onboarding & service provisioning
Build workflows with dependency sequencing, input validation, reusable configuration, and recovery procedures.
REST API integration
Create integrations using delegated authentication, permission enforcement, schema validation, and safeguards against duplicate operations.
Certificate-management automation
Automate enrollment, renewal, trust installation, and endpoint deployment, extending PKI work into repeatable administration.
Security assessments & endpoint reporting
Automate assessments, consolidate findings into structured remediation reports, and identify unauthorized remote-access software.
Administrative tool modernization
Develop PowerShell and .NET tools that integrate identity services, hardware security keys, and operator interfaces.
Repeatable software delivery
Engineer automated checks, dependency validation, package signing, controlled releases, and deployment verification.

Employment history

Current role

- Present

Full-time · Remote

Arrow Team

Senior Systems Engineer

Design, implement, and troubleshoot Azure and on-premises infrastructure for client environments. Work across systems architecture, automation, identity, security, and complex technical escalations, with a focus on resolving root causes and building maintainable systems.

  • Own Azure Virtual Desktop architecture, deployment, and optimization, including FSLogix, Azure Files, authentication, profile management, and performance troubleshooting.
  • Lead Active Directory security hardening and troubleshoot two-tier public key infrastructure (PKI), including certificate authority configuration, certificate deployment, and trust issues.
  • Recover and rebuild Windows Server and Active Directory environments, including domain controller replacement, SYSVOL and DFS replication remediation, DNS, and Group Policy troubleshooting.
  • Rebuild and troubleshoot Hyper-V infrastructure, addressing host configuration, clustering, networking, storage, and validation issues.
  • Develop PowerShell tools and Terraform workflows for repeatable infrastructure deployment, configuration, validation, and administrative tasks.
  • Build internal engineering tools with authentication workflows, package signing, automated testing, and deployment validation. Develop controlled release processes and recovery procedures.
  • Implement and troubleshoot server multifactor authentication and administrative access controls, including Duo and offline authentication requirements.
  • Serve as a senior escalation resource for complex infrastructure issues and project work. Coordinate technical testing, document dependencies and rollback plans, and prepare runbooks for ongoing support.

-

Full-time · Williston, Vermont

VC3

Implementation Engineer II

  • Delivered network and infrastructure projects, including firewall replacements, software-as-a-service (SaaS) implementations, and Layer 3 switch configuration and troubleshooting.
  • Integrated software-defined wide area network (SD-WAN) solutions and optimized routing, quality of service (QoS), and security configurations to improve connectivity and traffic management.
  • Led server migration projects, including live workload migrations to upgraded hosting hardware.
  • Migrated on-premises systems to Azure platform-as-a-service (PaaS) solutions.
  • Executed lift-and-shift migrations from private cloud infrastructure to public cloud environments.
  • Migrated workloads between public cloud and GCC-compliant environments.

-

Full-time · Williston, Vermont

VC3

Systems Engineer II

  • Designed and implemented Microsoft Azure Virtual Desktop solutions, integrating them into existing client environments.
  • Contributed to an interdepartmental runbook to improve troubleshooting consistency and streamline issue resolution.
  • Mentored technicians to strengthen technical knowledge and troubleshooting skills.
  • Served as a liaison between customers and vendors, communicating technical issues clearly to nontechnical audiences.
  • Received Employee of the Year recognition.

-

Full-time · Williston, Vermont

VC3

Service Desk Engineer

  • Set a company record for requests closed during a business week.
  • Created internal onboarding processes to streamline the experience for new employees.
  • Maintained a high first-call resolution rate.
  • Received Rookie of the Year recognition.

-

Full-time · Williston, Vermont

The University of Vermont Medical Center

Deskside Support Technician

  • Diagnosed and resolved desktop, laptop, operating system, and application issues.
  • Configured employee workstations, including hardware, peripherals, and software.
  • Investigated reported problems through diagnostic testing and direct communication with users.
  • Relocated and reconnected workstations and peripherals during office moves.

03 / Selected work

The work behind
the expertise.

Engineering case studies across infrastructure, operational software, security automation, and integration. Technical decisions and contributions, with client details kept confidential.

01

Identity
& recovery

Active DirectoryDFSRWindows Server

Recovering the foundations
of a Windows environment.

Separating directory health, SYSVOL replication, and file-namespace access to recover one service and isolate the next failure.

Verified progress

SYSVOL reached a normal replication state. A separate namespace failure was traced to an unavailable server dependency.

Read the case study
Environment
Windows directory services
My contribution
Recovery and root-cause investigation

The problem

A domain controller was not making its SYSVOL and NETLOGON shares available, even though Active Directory replication checks were healthy. SYSVOL carries the files used by Group Policy and logon scripts, so directory replication alone was not enough to establish that the controller was ready.

A separate file-access problem involved a Distributed File System (DFS) namespace. The work needed to distinguish a replication problem from a namespace dependency problem, rather than treating every symptom as the same failure.

The decisions

I used replication state and event evidence to establish the recovery sequence. One controller was designated as the authoritative SYSVOL source, and the affected partner was re-enabled non-authoritatively. That made the direction of recovery explicit.

I also kept the namespace investigation separate. A successful SYSVOL recovery would not, by itself, demonstrate that a mapped file path or its namespace targets were healthy.

The technical work

  1. Establish the actual replication state. Correlated healthy directory replication with missing shares, an Initial Sync state, and a DFS Replication event indicating that the controller was waiting for its partner.
  2. Recover SYSVOL with a defined source. Worked through the authoritative and non-authoritative recovery sequence, checked the primary initialization event, and confirmed the affected controller subsequently reached State 4, Normal.
  3. Trace the remaining access dependency. Checked the namespace object and running services, then investigated RPC failures and target connectivity. Name-resolution, network, RPC, and SMB checks exposed an unavailable server still referenced by the namespace.

What the evidence showed

Observed recovery evidence and its meaning
EvidenceWhat it established
Healthy AD replication; missing SYSVOL sharesThe directory and SYSVOL needed separate health checks.
DFSR Event 4602The designated primary completed SYSVOL initialization.
State 4 (Normal); SYSVOL path accessibleThe affected controller reached normal SYSVOL replication state, and SYSVOL access was confirmed.
Namespace RPC failure; unreachable targetA remaining file-access issue had a separate unavailable-server dependency.

Event and recovery-state reference: Microsoft’s SYSVOL troubleshooting guidance (opens in a new tab).

The result

SYSVOL recovery reached a confirmed normal state, and the investigation identified the dependency behind the separate namespace failure. Those were distinct findings: the replication milestone was verified, while namespace remediation remained follow-up work.

Engineering takeaway: Validate each layer of a service independently. A healthy directory, a healthy replicated share, and a working user access path are different checkpoints.

02

Security
& availability

Duo MFAYubiKeyAccess policy

Designing authentication
around operational risk.

Developing role-aware multi-factor authentication policies, with account matching, enrollment, and offline administrator access treated as separate design requirements.

Design decision

Match policy to the system’s role, and plan recovery access around the login methods that actually support it.

Read the case study
Environment
Domain-joined Windows servers
My contribution
Policy configuration and rollout planning

The problem

Adding multi-factor authentication (MFA) to server logons introduced questions that an agent installation could not answer: which account was being matched, what happened if the authentication service became unreachable, and how an administrator would access the system during recovery.

The environment included systems with different security and availability requirements. Existing Remote Desktop access also needed to remain usable, without restructuring directory groups or organizational units as part of the rollout.

The decisions

  • Configure by server role. Treat authentication-failure behavior as an explicit policy decision, with different system responsibilities considered separately.
  • Resolve identity matching. Account for Windows username formats and Duo account matching, so naming assumptions did not become an enrollment problem.
  • Plan offline activation separately. Include hardware-backed offline authentication in the administrator access plan, while distinguishing a registered account from an account activated for offline access on a particular system.
  • Respect the access method. Keep console and Remote Desktop scenarios separate when documenting the recovery path.

The important technical distinction

The selected security-key workflow required offline activation for each account on each Windows system. A key being available to an administrator did not mean offline access was ready everywhere.

Duo’s password-based offline U2F security-key flow supports local console logons. A key attached to a standard Remote Desktop client is not an equivalent offline authentication path to the remote server. That distinction shaped the recovery-access planning.

Product behavior reference: Duo’s Windows offline-access requirements (opens in a new tab).

Rollout checkpoints

The plan separated three states that can otherwise be mistaken for the same thing:

Policy configured
The intended server-role and authentication behavior is defined.
Account prepared
The account matches the expected identity, with the required enrollment and system-specific offline activation.
Access validated
The intended login method is exercised under the conditions it needs to support.

These are acceptance criteria, not a claim that every account and outage scenario was tested.

The result

The work established differentiated policy configuration and an offline-access plan with explicit account, enrollment, and connection-method requirements. It made the boundary between installing MFA and preparing a usable recovery path clear.

Engineering takeaway: Security controls and operational access have to be designed together. Recovery instructions need to work for the actual account, system, and connection method.

03

Automation
& delivery

PowerShellTerraformValidation

Making validation repeatable.
Keeping releases deliberate.

Moving validation into a local wrapper while retaining coverage for source, packages, compatibility, infrastructure, and release controls.

Verified outcome

Merged source matched the tested source. Validation remained separate from release and deployment.

Read the case study
Environment
Code and infrastructure delivery workflows
My contribution
Wrapper implementation and merge verification

The problem

Validation was moving out of GitHub Actions into a local workflow. The goal was to change where checks ran while retaining the coverage and release controls that already mattered: source contracts, compatibility, packaging, infrastructure, rollback, and signing.

The boundary between validation and execution was equally important. A successful test run needed to be useful on its own, without publishing a package, triggering a release, or changing live infrastructure.

The implementation

I implemented a local wrapper, updated the tests and documentation, and retained manual packaging, signing, publishing, and deployment workflows.

Parallel checks
Run independent validation work concurrently within the wrapper.
Pinned dependencies
Use defined dependency versions so the execution environment is reproducible.
Isolated environments
Keep test execution separate from the working environment and include cleanup.
Timing reports
Make execution time visible rather than assuming an optimization produced a measurable gain.

Preserving the checks

The wrapper retained multiple kinds of evidence instead of reducing validation to a single build command:

  • Source and compatibility: source-contract checks and Windows PowerShell compatibility checks.
  • Packaging and operations: package and runbook checks, alongside retained release, signing, and rollback coverage.
  • Behavior and infrastructure: mock-based tests and Terraform validation across multiple stacks.

Expected offline-dependent skips were documented separately. A skipped check was not counted as a pass, and Terraform validation was not treated as evidence that infrastructure had been deployed.

Closing the verification loop

  1. Validate the integrated source. Incorporate the current main branch and run the relevant checks against that combined state.
  2. Merge the completed work. Keep the validation change separate from the manual release and deployment workflows.
  3. Compare after the merge. Verify that the merged source matched the source that had actually been tested.

This last comparison mattered: a passing pre-merge run would not, on its own, establish that the final merged source was the same.

The result

The integrated validation work passed its recorded source-contract checks, additional suites, and Terraform validation. Completed changes were committed, pushed, and merged, and the merged source was verified against the tested source.

The merges did not trigger releases, deployments, live infrastructure changes, or GitHub Actions runs. Validation moved locally while publication remained a separate, deliberate action.

Engineering takeaway: Repeatability is more than rerunning a command. It includes controlled inputs, visible exceptions, preserved coverage, and evidence that the code being delivered is the code that was tested.

04

Software
& integration

PowerShell / .NETIdentityREST APIs

Building secure
operational tooling.

Developing operational applications that connect authenticated interfaces, privileged tasks, background jobs, and external services.

Engineering focus

Make permissions, dependencies, and job state part of the application’s design.

Read the case study
Work area
Operational applications and service provisioning
My contribution
Application, workflow, and integration engineering

The problem

An administrative interface can start a task without making its dependencies, permissions, or progress clear. Onboarding and provisioning also involve multiple steps, so a partial failure needs a recovery path that accounts for work already completed.

The engineering approach

  • Connect the interface to an execution model. Build authenticated operator interfaces with background-job orchestration and status reporting.
  • Define the access boundaries. Integrate identity services, managed identities, centralized credential handling, and permission enforcement around privileged operations.
  • Make workflows repeatable. Sequence dependencies, validate inputs, reuse configuration, and include recovery procedures.
  • Handle API operations deliberately. Use delegated authentication, validate schemas, and add safeguards against duplicate operations.

Implementation scope

My work spans PowerShell and .NET administrative tools, identity and hardware-security-key integration, operator interfaces, and REST integrations. Automated checks, dependency validation, signing, and controlled release processes support the delivery side of that work.

Engineering takeaway: A useful operational tool makes access, execution state, and recovery understandable to the person running it.

05

PKI
& automation

PKICertificatesEndpoints

Automating certificate
lifecycle operations.

Extending certificate authority and trust troubleshooting into automation for enrollment, renewal, trust installation, and endpoint deployment.

Engineering focus

Work through issuance, endpoint placement, and trust as connected parts of certificate administration.

Read the case study
Work area
Certificate services and endpoint integration
My contribution
PKI engineering and administrative automation

The problem

A certificate being issued does not establish that an endpoint has the right certificate or trusts its issuer. Renewal adds another recurring operation, with its own dependencies on enrollment, installation, and trust configuration.

The engineering approach

  • Automate enrollment and renewal. Turn recurring certificate-administration tasks into repeatable workflows.
  • Include endpoint deployment. Address certificate placement and installation as part of the workflow.
  • Handle trust explicitly. Include trust installation and investigate certificate-chain issues alongside authority configuration.
  • Keep troubleshooting connected to the workflow. Distinguish enrollment, renewal, deployment, and trust when identifying where an operation needs attention.

Implementation scope

My contribution combines two-tier PKI troubleshooting with automation for enrollment, renewal, trust installation, and endpoint deployment. The work connects certificate services to the systems that need to consume them.

Engineering takeaway: Certificate automation needs to account for how a certificate reaches the endpoint and becomes trusted, as well as how it is issued.

06

Security
& reporting

AssessmentsEndpoint reportingData processing

Turning security assessments
into actionable reports.

Combining assessment automation, endpoint reporting, and structured findings so technical observations can inform remediation work.

Engineering focus

Carry the finding and its context into a report someone can use.

Read the case study
Work area
Security assessment and endpoint visibility
My contribution
Automation, data processing, and report generation

The problem

Assessment tools and endpoint data can produce useful observations in different formats. Turning those observations into follow-up work requires consolidation and enough context for a reviewer to understand what needs attention.

The engineering approach

  • Automate assessment and reporting tasks. Connect tool output and endpoint information to a repeatable reporting workflow.
  • Consolidate the findings. Process assessment data into structured remediation reports.
  • Include remote-access software visibility. Identify unauthorized remote-access software as part of the assessment work.
  • Design for operational use. Organize technical findings so they can be reviewed and carried into remediation planning.

Implementation scope

This work covers assessment automation, endpoint reporting, tool integration, data processing, and remediation-report generation. Reports provide findings for review; remediation execution and verification are separate activities.

Engineering takeaway: The reporting workflow matters as much as collection. Findings need to remain understandable when they reach the person responsible for follow-up.

07

Architecture
& visualization

Azure networkingTopologyConfiguration

Visualizing cloud
and network dependencies.

Connecting infrastructure discovery, routing analysis, topology visualization, and configuration validation to make dependencies easier to reason about.

Engineering focus

Explain the expected network path and the configuration that supports it.

Read the case study
Work area
Cloud networking and topology tooling
My contribution
Network analysis, visualization, and configuration tooling

The problem

A diagram can show that networks are connected while leaving route selection, gateway dependencies, or inspection paths unclear. Configuration and observed behavior need to be considered alongside the topology.

The engineering approach

  • Map the relevant dependencies. Bring infrastructure information, connectivity, and configuration into a view that supports analysis.
  • Reason through the path. Examine hub-and-spoke connections, site-to-site VPNs, gateway transit, propagated routes, and firewall paths.
  • Connect the visual to configuration. Use topology and network-configuration tooling to make relationships and validation work easier to follow.
  • Distinguish design from observation. Treat a proposed path, configured path, and observed traffic behavior as different forms of evidence.

Implementation scope

This work brings together Azure network design and path analysis with topology visualization and configuration tooling. My independent network-configuration projects are described separately below.

Engineering takeaway: A useful topology view explains dependencies and supports investigation. A connection on a diagram is only one part of the evidence.

Case studies omit client names and identifying environment details. Technical scope, design decisions, and verified outcomes are described separately.

04 / Independent software

A broader
development practice.

Personal software projects outside my employment work, spanning developer tools, privacy, desktop applications, and integration.

01

Network configuration tools

Tools for working with network configurations across vendors, including configuration translation and topology visualization.

02

Privacy middleware

Middleware projects focused on privacy and the handling of data between applications and services.

03

Editor & browser extensions

Extensions that bring custom workflows into the tools used for development and everyday browsing.

04

Desktop telemetry

Desktop software for presenting system telemetry through a usable interface.

05

Synchronization applications

Applications for coordinating data and state across connected tools and environments.

05 / How I work

Architecture with
an operational perspective.

I work from requirements through implementation, troubleshooting, and support. Across infrastructure and software, I focus on understanding dependencies, making the tradeoffs clear, and verifying the complete workflow.

  1. 01

    Find the cause.

    Start with evidence. Separate the symptom from the underlying dependency before deciding what to change.

  2. 02

    Keep the solution practical.

    Make the smallest complete change that addresses the problem. Reduce unnecessary complexity and make the tradeoffs clear.

  3. 03

    Verify and leave a clear handoff.

    Check the complete workflow, record what changed, and document the outcome and any remaining work.

Continue the conversation

Let’s talk engineering.

To discuss cloud architecture, operational software, security tooling, or integration projects, find me on LinkedIn.

Connect on LinkedIn (opens in a new tab)