Introduction

At ShitOps, we strive to push the boundaries of what's possible with our infrastructure. Recently, we faced a unique challenge: enabling seamless, millisecond-level deployment of Homebrew packages on iPads connected through Cisco AnyConnect VPN, all while leveraging Prometheus for real-time monitoring.

The objective was to empower developers to instantly deploy critical tools onto their iPads regardless of their network environment, ensuring uptime and consistent package management. In this post, I'll walk you through our multi-layered, state-of-the-art solution integrating Cisco AnyConnect, advanced VPN tunneling, containerization, edge computing, and Prometheus metrics.

Understanding the Problem

Homebrew is a powerful package manager primarily used on macOS and Linux, but iOS (and thus iPadOS) lacks native support due to Apple's stringent app management policies. Typical workarounds fail to provide rapid deployment and seamless VPN integration.

Our developers use iPads extensively and require the ability to rapidly install and update Homebrew packages through secure VPN tunnels managed by Cisco AnyConnect. Achieving millisecond-level deployment latency over possibly fluctuating network conditions was critical to maintain productivity.

Architectural Overview

To solve this, we pioneered an architecture that orchestrates several cutting-edge technologies:

  1. iPad Edge Processing Agent (IEPA): A custom-built iPad application developed with SwiftUI and embedded Rust modules to act as a container host and orchestrator.

  2. Cisco AnyConnect Advanced Tunneling (CAAT): Extending Cisco AnyConnect VPN with custom binary extensions enabling low-latency multiplexed channels.

  3. Homebrew Container Microservices: Packaging each Homebrew formula as lightweight OCI containers, stored in a private Harbor registry, deployable on iPads.

  4. Real-time Deployment Pipeline (RDP): Implemented using Kubernetes Operators that listen to deployment events and trigger container pushes.

  5. Prometheus Monitoring Mesh: A federated Prometheus cluster capturing granular millisecond metrics at each stage.

Detailed Technical Solution

iPad Edge Processing Agent (IEPA)

IEPA runs on each iPad under a specialized enterprise-signed profile. It is responsible for container runtime management using a custom shim around the Firecracker microVM, adapted for iPadOS constraints. This shim is written in Rust for performance and safety.

The IEPA communicates over an encrypted gRPC channel tunneled through Cisco AnyConnect's CAAT extensions, enabling multiplexed streams with minimal overhead.

Cisco AnyConnect Advanced Tunneling (CAAT)

Building on top of Cisco AnyConnect, we introduced CAAT, which injects a user-mode kernel extension that provides multiplexed tunneling channels. This innovation drastically reduces handshake times and packet overhead, allowing sub-5ms round-trip latency for packet delivery.

These channels prioritize container image layer downloads, improving Homebrew formula deployment speeds dramatically.

Homebrew Container Microservices

To accommodate iPadOS's limitations, traditional Homebrew formulas are converted into OCI-compliant container images using a custom tool named brew2oci. Each formula is encapsulated as a container with a minimal base OS and all dependencies pre-installed.

Images are pushed to a private Harbor registry with redundancy and geo-replication to optimize pull times for various developer locations.

Real-time Deployment Pipeline (RDP)

At deployment time, developers trigger the pipeline via a custom CLI tool integrated with their iPad and the central CI/CD system.

The central Kubernetes cluster runs Operators listening for deployment CRDs (Custom Resource Definitions) and orchestrates container builds with Kaniko, pushes to Harbor, then sends notification events to IEPA agents.

On the iPad, IEPA receives deployment directives, pulls images via CAAT tunnels, and initializes microVMs running the respective Homebrew package.

Prometheus Monitoring Mesh

To achieve complete observability, we deployed a federated Prometheus monitoring system:

All metrics are aggregated and visualized via Grafana dashboards, enabling pinpoint analysis of any latency bottlenecks down to the millisecond.

System Flow Diagram

sequenceDiagram participant Dev as Developer participant CLI as Custom CLI participant K8s as Kubernetes Cluster participant Harbor as Harbor Registry participant Cisco as Cisco AnyConnect + CAAT participant IEPA as iPad Edge Processing Agent Dev->>CLI: Trigger Homebrew package deployment CLI->>K8s: Submit deployment CRD K8s->>Harbor: Build and push OCI container image K8s->>IEPA: Notify deployment event over secure channel IEPA->>Cisco: Establish multiplexed tunnel IEPA->>Harbor: Pull container image via CAAT tunnel IEPA->>IEPA: Spin up microVM and launch package IEPA->>Prometheus: Push deployment metrics Cisco->>Prometheus: Export tunnel latency metrics K8s->>Prometheus: Export pipeline metrics Prometheus->>Grafana: Visualize metrics

Performance and Results

By leveraging this multi-faceted approach, we consistently achieved:

This dramatically improved developer experience and reliability across ShitOps’ distributed iPad fleet.

Conclusion

While integrating Homebrew on iPads with Cisco AnyConnect VPN and achieving millisecond-level deployment latency is challenging, our comprehensive solution demonstrates the power of combining container microservices, edge processing, VPN tunneling enhancements, and unified observability.

At ShitOps, we continue exploring innovative and pioneering engineering techniques to optimize infrastructure performance for all devices, no matter how unconventional the platform. Stay tuned for more groundbreaking solutions!


Dr. Chuck Binary Lead Systems Architect at ShitOps


Note: All system components described are proprietary and tailored specifically for ShitOps engineering teams.