Hire the Best Microsoft Windows Powershell Specialists
in Canada

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Matthew C.

Airdrie, Canada

$60/hr
5.0
60 jobs

Microsoft 365 a mess? I fix SharePoint and Teams sprawl, stuck migrations, manual approvals, Power Automate workflows, and Copilot/AI readiness so your business runs from one clean system. I am one of North America's most experienced Microsoft 365 and SharePoint architects. For over 20 years, I have turned complex, fragmented environments into connected, governed digital workplaces people can actually run. Clients use me as both an M365 architect and SharePoint guru because I see business process, information architecture, security, migration, automation, and AI as one problem. Show me how your business works and I will find the cleanest, most maintainable path through it. **Microsoft 365, SharePoint, Teams & modern workplace** • SharePoint Online architecture, intranet design, hub sites, document management, libraries, lists, metadata, content types, taxonomy, search, navigation, sharing, permissions, branding, JSON formatting, modern UX, accessibility, dashboards, provisioning, lifecycle management, and site modernization • Microsoft Teams collaboration, workspace design, channels, external sharing, guest access, Teams governance, adoption, lifecycle automation, Teams Voice, Teams Phone, and Direct Routing • Office 365 / M365 across OneDrive, Exchange Online, Outlook, Microsoft Forms, Viva, Planner, Power BI, and Entra ID **Automation, Power Platform & business process** • Business automation, business process automation, and workflow automation for intake, approvals, onboarding, document generation, email automation, task routing, reporting, exception handling, audit trails, and human review • Power Automate, Power Automate Administration, Power Apps, Power Platform, Dataverse, APIs, webhooks, custom connectors, Microsoft Graph API, PowerShell, and PnP PowerShell • Workflow recovery, flow troubleshooting, legacy workflow modernization, InfoPath replacement, Nintex replacement, forms automation, data integration, system integration, and maintainable low-code solutions **Copilot, ChatGPT, AI agents & AI automation** I move organizations from AI experiments to production workflows: Microsoft 365 Copilot, Copilot readiness assessments, Copilot Studio, ChatGPT, custom GPTs, AI Agent Development, agentic AI, knowledge base automation, prompt engineering, data readiness, AI governance, guardrails, logging, human-in-the-loop approvals, MCP, API integration, and agents that work across documents, email, tasks, databases, and business systems. AI works when source material, permissions, ownership, and exception paths are clear. I put structure and security around agents so they can summarize, classify, draft, compare, route, update, and notify without becoming another ungoverned system. **Migration, modernization, recovery & coexistence** • Tenant-to-tenant migration, tenant separation, M&A integration, cross-tenant synchronization, B2B collaboration, SharePoint migration, Teams migration, OneDrive migration, Exchange and mailbox migration, file share migration, Google Workspace to Microsoft 365, legacy platform replacement, and post-migration cleanup • Discovery, inventory, mapping, migration waves, pilot, pre-stage, delta sync, cutover, rollback, validation, permissions, metadata, version history, ownership transition, adoption, training, hypercare, and knowledge transfer **Governance, security & compliance** Governance-first design across Microsoft Purview, DLP, retention, sensitivity labels, eDiscovery, legal hold, Conditional Access, MFA, least privilege, external sharing, access reviews, audit logging, Secure Score, data classification, records management, lifecycle policies, risk registers, and remediation. **Proof from real environments** • Led a 52TB SharePoint Online modernization across 30 departments, including information architecture, metadata, migration, governance, automation, training, and adoption • Delivered tenant separations and Microsoft 365 migrations involving 3,000+ users/mailboxes and multi-terabyte content, plus migration recovery when previous moves left environments unusable • Designed SharePoint lifecycle and governance remediation for a 5,000+ site estate, plus legal intake, onboarding, document, reporting, email/security, and cross-platform automation for regulated organizations • Worked across Fortune 500, government, financial services, healthcare, legal, education, energy, retail, manufacturing, nonprofits, enterprise, and mid-market organizations I start with discovery and current-state mapping, then create future-state architecture, a roadmap, risk register, implementation plan, and clear scope. I deliver the documentation, runbooks, testing, UAT, training, and handoff your team needs to support it. If your workplace is messy, manual, half-migrated, hard to govern, or not ready for AI, bring me the whole problem. I will simplify it, automate what should be automated, reduce risk, improve collaboration, save time, and reduce errors.

  • Microsoft Windows PowerShell
  • Microsoft SharePoint
  • Microsoft Power Automate
  • Microsoft 365 Copilot
  • Migration
  • Microsoft Teams
  • Office 365
  • Microsoft PowerApps
  • AI Agent Development
  • Business Process Automation
  • Microsoft Power BI
  • Google Workspace
  • Automation
  • Microsoft Power Automate Administration
  • Artificial Intelligence
  • Microsoft SharePoint Development
  • Microsoft SharePoint Administration
  • Microsoft Azure
  • Email Security
  • API Integration
David L.

Sylvan Lake, Canada

$12/hr
5.0
1 jobs

Microsoft 365 & Exchange Expert | Email Security | Mail Flow | PowerShell Automation | L3 Support Building My Upwork Portfolio Currently growing my presence on Upwork, offering competitive rates while delivering enterprise-level support backed by 10+ years of real-world experience managing large-scale environments (100K+ users). I’m a Senior Messaging Engineer specialized in Microsoft 365 and Exchange (On-Prem & Online), focused on mail flow, email security, and advanced troubleshooting (L3). I help organizations keep their messaging environments secure, stable, and optimized. What I can help you with -Microsoft 365 / Exchange Exchange Online & Hybrid environments Mail flow troubleshooting (connectors, routing, delivery issues) Transport rules analysis and optimization Mailbox issues, outages, and escalations (L3 support) -Email Security Phishing & spam investigations Junk email analysis (why emails are classified as spam) Microsoft Defender / EOP troubleshooting Email authentication (SPF, DKIM, DMARC) -Automation (PowerShell) Task automation & reporting scripts Mail flow and message trace analysis Bulk operations and admin tasks Custom scripts for monitoring and troubleshooting -Migrations & Integrations Microsoft 365 migrations (cutover, hybrid, staged) Mailbox moves and post-migration validation Outlook / mobile / client connectivity support Why work with me 10+ years supporting enterprise messaging environments Real L3 experience handling critical issues and escalations Strong troubleshooting mindset (I don’t guess, I find root cause) Focused on security + stability + automation Tech Stack Microsoft 365 | Exchange Online | Exchange On-Prem Microsoft Defender | EOP | Cisco IronPort PowerShell | Microsoft Graph API Active Directory | Entra ID Outlook | Teams | SharePoint | OneDrive

  • Microsoft Windows PowerShell
  • Microsoft Outlook
  • Microsoft Teams
  • Microsoft Exchange Server
  • Microsoft Exchange Online
  • Email Security
  • Microsoft Intune
  • Microsoft Power Automate
  • Email Support
  • Messaging System
  • Load Balancing
  • SMTP
  • Microsoft Active Directory
  • Microsoft Message Queue Server
  • Customer Service
  • Customer Satisfaction
  • PHP Script
Church E.

Oakville, Canada

$35/hr
5.0
13 jobs

I am a highly motivated Information Technology specialist with experience in the Business Process Outsourcing sector, excellent interpersonal skills, and over four years of working experience in cloud computing and Information Technology support services. I have an excellent track record of providing outstanding service and support to colleagues and clients in various business sectors.

  • Microsoft Windows PowerShell
  • Customer Support
  • Microsoft Office
  • Email Communication
  • Helpdesk
  • Microsoft Active Directory
  • Microsoft Exchange Online
  • Office 365
  • Cloud Implementation
  • Cloud Migration
  • Technical Support
  • Microsoft Azure
  • Customer Service
  • Google Workspace Administration
  • Salesforce
Alfred O.

Toronto, Canada

$40/hr
4.9
23 jobs

I am an experienced IT support professional with extensive knowledge of computer hardware and software, and solid background in bespoke customer support services. I am experienced in Enterprise Office Support and Office 365 administration which includes; Exchange Online, SharePoint Online, OneDrive for Business, Skype for Business & Microsoft Teams. I have excellent communication skills when it comes to explaining technical terms to a layman's understanding, and also good troubleshooting skills on client applications running on Windows computers, Mac, and Mobile devices. Technologies: *Office 365 *Windows/ Mac OS *Azure Active Directory *PowerShell *Active Directory

  • Microsoft Windows PowerShell
  • Windows Administration
  • Usability Testing
  • Atlassian Confluence
  • Functional Testing
  • Customer Support
  • Web Testing
  • Microsoft Outlook
  • Computer Network
  • Microsoft Exchange Online
  • Email Support
  • Office 365
  • Incident Management
  • Technical Support
  • Microsoft Azure
Deepak K.

Halifax, Canada

$30/hr
5.0
87 jobs

I help MSPs and growing businesses manage Microsoft 365, Azure, Intune, RMM, and Windows infrastructure — from complex troubleshooting and technical escalations to endpoint management, security hardening, and PowerShell automation. With hands-on experience supporting 1,200+ endpoints across fast-paced, multi-client environments, I take ownership of technical issues from investigation through resolution while keeping communication clear and documentation accurate. My work spans Microsoft cloud, endpoint management, Windows infrastructure, virtualization, security, and RMM operations. I’m particularly effective when issues cross multiple technology layers and require more than a quick fix. 🔹 MICROSOFT 365 & AZURE • Exchange Online, Teams, SharePoint, and OneDrive • Azure and Entra ID / Azure AD administration • MFA, Conditional Access, and identity management • Mail flow, authentication, and access troubleshooting • Microsoft 365 security and tenant administration 🔹 INTUNE & ENDPOINT MANAGEMENT • Device enrollment and configuration • Compliance policies and security baselines • Application deployment and remediation • BitLocker management • Windows troubleshooting and endpoint hardening 🔹 RMM, MONITORING & MSP OPERATIONS • N-able N-central monitoring, patching, and remediation • RMM policy management and endpoint administration • Alert investigation, tuning, and escalation workflows • Proactive endpoint and server health monitoring • ConnectWise ticket workflows and documentation • SLA-driven technical support across multi-client environments 🔹 WINDOWS SERVER & INFRASTRUCTURE • Active Directory and Group Policy • DNS, DHCP, and file server administration • Windows Server troubleshooting and maintenance • Remote Desktop Services • Azure Virtual Desktop and FSLogix troubleshooting • Server performance and infrastructure remediation 🔹 SECURITY & ENDPOINT PROTECTION • CrowdStrike deployment and remediation • Huntress monitoring and response support • Conditional Access and identity security • Endpoint hardening • Vulnerability and patch remediation • Security incident investigation support 🔹 VIRTUALIZATION, BACKUP & NETWORKING • VMware ESXi administration and troubleshooting • Virtual machine deployment and maintenance • Backup monitoring and recovery support • FortiGate firewall administration and troubleshooting • Infrastructure health checks and remediation 🔹 POWERSHELL & AUTOMATION • Automated remediation scripts • Microsoft 365 administration automation • RMM-based scripting and self-healing workflows • Endpoint maintenance automation • Custom reporting and health checks • Automation of repetitive operational tasks WHY CLIENTS WORK WITH ME • Take ownership of technical issues from investigation through resolution • Troubleshoot across cloud, endpoint, server, virtualization, and network layers • Focus on root-cause analysis rather than temporary fixes • Communicate professionally with end users, stakeholders, and technical teams • Maintain clear, audit-ready documentation • Identify recurring issues and automate remediation where possible • Work effectively across fast-paced, multi-client environments For MSPs, I understand the realities of managed services: multiple client environments, competing priorities, SLA pressure, noisy RMM alerts, escalations, documentation requirements, and after-hours maintenance. For growing businesses, I provide reliable hands-on administration and troubleshooting across Microsoft cloud, endpoints, servers, security, and infrastructure. If you need an engineer who can take ownership of Microsoft cloud, infrastructure, RMM, endpoint, or automation work, I’d be happy to discuss your environment.

  • Windows Administration
  • Office 365
  • Microsoft Azure
  • System Administration
  • Backup Administration
  • DNS
  • FortiGate Firewall
  • Cloud Migration
  • Microsoft Intune
  • VPN
  • Microsoft Exchange Online
  • Managed Services
  • Network Security
  • Domain Migration
  • Email Security
Luke P.

Fredericton, Canada

$53/hr
5.0
13 jobs

Pleasure to meet you! I’m Luke. For 20+ years, I've been turning messy, time-eating processes into clean, automated systems, giving money and time back to business owners. Some examples: ➡️ Automated $15B+ in financial reconciliations at an oil refinery, cutting weeks of bookwork down to minutes ➡️ Streamlined an organization's IT onboarding and offboarding, cutting costs 95% ➡️ Designed data pipelines that slashed reporting costs by 350X and freed teams from hours of manual work What I Do ----------- I turn complicated, repetitive tasks into rock-solid, automated workflows. Whether it’s onboarding 1,000 contractors in a week or cleaning up a messy back office, I make your processes consistent, scalable, and built to last. Then I automate them so you never have to think about them again. You get predictable results, faster and cheaper, and more time for what really matters: growing your business.

  • Microsoft Windows PowerShell
  • Zapier
  • Make.com
  • ChatGPT
  • Microsoft Excel
  • Google Sheets
  • Scripting
  • Task Automation
  • Python
  • Microsoft VBScript
  • Visual Basic for Applications
  • Automation
  • Data Extraction

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