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Tosh Systems — Enterprise Homelab Infrastructure

This repository documents the infrastructure supporting a fictional organization called Tosh Systems.

The objective is to replicate enterprise IT environments using Microsoft 365 cloud services, virtualization, containerization, networking, automation, and security — built and documented as if supporting a real organization.

⚠️ Security Notice

This repository contains sanitized documentation and example configurations of my homelab environment.

  • No real credentials, API keys, or secrets are included
  • All domains, IP addresses, and identifiers are redacted or replaced with placeholders
  • Configuration files are provided as examples only

This project is intended to demonstrate architecture, security practices, and system design, not expose a live environment.


Hardware

  • UGREEN DXP4800 Plus (Intel Pentium Gold 8505, 8GB DDR5)
  • Crucial P310 500GB NVMe (hypervisor boot drive)
  • 4x HDD bays (expanding for storage + redundancy)

Stack

  • Hypervisor: Proxmox VE
  • Identity & Cloud: Microsoft 365 / Entra ID, Intune (planned)
  • Containers: Docker + Docker Compose
  • Networking: Tailscale (secure remote access)
  • Monitoring: Grafana + Uptime Kuma
  • Media Server: Jellyfin
  • Web Access: Nginx Proxy Manager (reverse proxy + SSL)
  • DNS: Pi-hole (internal DNS) & Cloudflare (external DNS + domain)

Architecture

Architecture Diagram Network Diagram

Diagrams are redacted to remove sensitive network details. See docs/architecture/ for full documentation.

Services

Service Purpose Status
Microsoft Entra ID Cloud identity + access Planned
Microsoft Intune Endpoint management Planned
Exchange Online Email Planned
Proxmox VE Hypervisor Planned
Tailscale Zero trust vpn Planned
Jellyfin Media server Planned
Nginx Proxy Manager Reverse proxy + SSL Planned
Pi-hole Internal DNS + Ad blocking Planned
Cloudflare External DNS + Domain Planned
Docker Container runtime Planned
Grafana Monitoring dashboard Planned
Uptime Kuma Service uptime monitoring Planned

Security Approach

Layer Implementation
Identity Entra ID + Conditional Access + MFA
Access Gateway Cloudflare Access (Entra-integrated SSO for self-hosted apps)
Network Tailscale zero trust mesh
Proxy Nginx Proxy Manager access lists
Application Per service authentication
Secrets .env files, never committed
DNS Pi-hole internal, Cloudflare external

See docs/security/ for full details.


Case Studies

Study Description Status
Entra ID Identity Design Tenant setup, users, groups, roles, naming conventions Planned
Intune Endpoint Management Device enrollment, compliance, configuration profiles Planned
Conditional Access Zero trust access policies + MFA enforcement Planned
Microsoft 365 DNS Domain verification, Exchange, SPF/DKIM/DMARC via Cloudflare Planned
Proxmox Setup Hypervisor install + VM architecture Completed
Tailscale Access Zero trust remote access implementation Ongoing
Reverse Proxy Nginx Proxy Manager + SSL setup Planned
DNS Architecture Pi-hole + Cloudflare split DNS Planned
Monitoring Stack Grafana + Uptime Kuma deployment Planned
Jellyfin Media server behind reverse proxy Planned
Authentication Multi layer auth implementation Planned
Automation Alerting and script automation Planned
Backups Proxmox Backup Server setup Planned

About

Enterprise infrastructure lab - documented as a simulated IT environment named Tosh Systems. Using Proxmox, Microsoft Entra-ID, Docker, and Cloudflare.

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