Guide

Cloudflare

A reading guide to running Cloudflare Zero Trust at enterprise scale — the migration, the policy model underneath it, and the operational detail that only appears once real users depend on it.

Reading guide

Cloudflare Zero Trust is not a product you install. It is a set of decisions about identity, device trust and application access that you keep making for years after the rollout is declared finished — and most of the difficulty lives in those decisions rather than in the configuration that expresses them.

What follows is everything published here on the subject, grouped into routes rather than listed by date. The order matters, because these problems arrive in a particular sequence and it is not the one you would choose. Broad access comes before narrow policy, because people have to keep working. Denials become a support problem before they become a design problem. Policy-as-code arrives late, usually just after a manual change has gone somewhere it should not have.

This is enterprise experience rather than a homelab walkthrough. The material comes from a multi-year programme replacing a legacy corporate VPN across a distributed organisation, discussed publicly in a Cloudflare webinar and on stage at Cloudflare Connect. Every configuration example is synthetic; no production architecture, tenant detail or policy appears anywhere on this site.

  1. Start here: what replacing a VPN actually involves

    The programme before the product. Read these three in order if you are deciding whether to start.

    1. Lessons from Replacing a Legacy VPN with ZTNA
    2. Browser vs Network-Centric Zero Trust
    3. Designing Zero Trust for Failure
  2. Policy design, and why egress is the hard part

    Where most implementations quietly go wrong: policy written against addresses that were never stable.

    1. Why IP-Based Egress Steering Does Not Scale
    2. DNS Names vs IPs for Egress Policy
    3. Dynamic Cloudflare Lists from Provider IPs
    4. Turning Remote Feeds into Terraform Policy Inputs
    5. Zero Trust Allow Lists with Workers KV
    6. Workers KV Is Backup, Not Source of Truth
  3. Device posture and the client

    The half of the access decision that is not identity, and the routing behaviour it depends on.

    1. Managing Device Posture as Code
    2. Cloudflare WARP Configuration as Code
    3. WARP Fallback Domains vs Split Tunnels
    4. Derive WARP Routes from Infrastructure
    5. Device Registrations Assign Virtual IPs
  4. Making enforcement legible

    A control that fires without explaining itself becomes a support ticket saying the internet is broken.

    1. Making Cloudflare Access Denials Actually Useful
    2. Building a Better Cloudflare Gateway Block Page
    3. Cloudflare Gateway Custom Block Page
    4. Gateway Block Pages Need Policy Context
    5. Resolve Gateway Rule IDs Before Showing Them
    6. Cloudflare Access Denied Information Page
  5. Conditional access on signals Cloudflare does not hold

    Gating access on an external system, and what must happen when that system cannot be reached.

    1. Gating Cloudflare Access on Training Completion
    2. Cloudflare Access Checks Must Fail Closed
    3. Cloudflare Training Compliance Gateway
    4. Bounded Retries for Cloudflare API Calls
  6. Deploying policy as code

    Getting changes out of the dashboard and into something reviewable, repeatable and reversible.

    1. Safe Cloudflare Zero Trust Pipelines
    2. A Multi-Cloud Zero Trust Lab, Built in Terraform
    3. Cloudflare Multi-Cloud Zero Trust Demo
    4. Cloudflare DNS Ad Blocking with Terraform
    5. Cloudflare Gateway Ad Blocking with Terraform
  7. Operating it

    Two pieces about the running service rather than the build.

    1. Zero Trust: Find the Failed Control Plane
    2. Cloudflare Allowed Domain Handler
  8. Not Zero Trust: running a site on Cloudflare Workers

    These carry the same tag because newcombe.dev is itself a Worker. Separated so they do not muddle the material above.

    1. Astro: GitHub to Cloudflare Workers
    2. CSP Nonces in Cloudflare Workers
    3. Cloudflare www-to-Apex Redirect
Everything above, by kind

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Long-form writing tagged Cloudflare.

Today I Learned

Short notes and fixes tagged Cloudflare.

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