CC deploying-tailscale-for-zero-trust-vpn
Deploys and configures Tailscale (or self-hosted Headscale) as a WireGuard-based zero trust mesh VPN, setting up identity-aware ACLs, exit nodes, subnet routers, and MagicDNS for encrypted peer-to-peer connectivity. Use when replacing traditional VPN servers with an identity-authenticated mesh network or enforcing granular per-device access control lists.
Deploys and configures Tailscale (or self-hosted Headscale) as a WireGuard-based zero trust mesh VPN, setting up identity-aware ACLs, exit nodes, subnet…
As a process C 51/100 · Has gaps — weak spots: result and completion, when it triggers, failures and branches
How to improve
- Your own cases (evals/evals.json, 4–6 real requests with expected answers): the full check would then run those instead of a model-drafted suite.
- A spec.yaml with trigger phrases and assertions — a behaviour contract for CI; `skilltest init` writes a template.
Guard findings · 4
✓ No critical or high findings
Medium and low: 4
-
low Dangerous commands
cmd-pipe-to-shell-known-hostSKILL.md:82Pipe-to-shell installer from a well-known host (still executes remote code) (documentation of a security skill)curl -fsSL https://tailscale.com/install.sh | sh
security skill -
low Dangerous commands
cmd-privilegeSKILL.md:270Privilege escalation / world-writable permissions (documentation of a security skill)echo 'net.…ard = 1' | sudo tee -a /etc/sysctl.conf
security skill -
low Dangerous commands
cmd-privilegeSKILL.md:271Privilege escalation / world-writable permissions (documentation of a security skill)echo 'net.…ing = 1' | sudo tee -a /etc/sysctl.conf
security skill -
low Dangerous commands
cmd-privilegeSKILL.md:313Privilege escalation / world-writable permissions (documentation of a security skill)sudo mv head…d64 /usr/local/bin/headscale
security skill
Files scanned: 8. Evidence is masked. Grey chips explain why severity was lowered.
Against the Agent Skills spec
- note
frontmatter-keyunknown frontmatter key "domain" - note
frontmatter-keyunknown frontmatter key "subdomain" - note
frontmatter-keyunknown frontmatter key "nist_csf" - note
frontmatter-keyunknown frontmatter key "mitre_attack"
Process rating: all ten parameters 51/100
- 0Result and completion. Does not say what the result is
- 0Failures and branches. Linear process with no failure handling
- 0Progress reporting. Says nothing while it works
- 20When it triggers. No condition that starts the skill
- 30Running it twice. 6 mutating operations with no state check
- 60Tools and files. Uses tools (node) that frontmatter does not declare
- 70Inputs and preconditions. Inputs and preconditions are listed
- 100Steps. 15 steps
- 100Consistency. Name and required fields are in place
- 100Execution cost. Instruction body is 2693 tokens
- medium Safety rules and hard prohibitions inside a skill: they belong in the system prompt, here they protect nothing
- low 14 top-level sections: this looks like several domains in one skill
Everything here is measured from the skill text rather than judged by a model, so the numbers are checkable. A parameter weighs more when it is a more common reason for the process to stall.
Quality signals
- +5Description has no quoted example phrases that should trigger the skill
- +4Description does not say when NOT to use the skill (false activations)
- +3Output format is not stated: the model decides each time
- -43 reference files, but SKILL.md never points to them: the model will not open them
- -32 of 2 scripts are never mentioned in SKILL.md
- +2Single-language instructions
- +3Description length 357: enough signal without eating the budget
- +4Structure: 26 headings
- +3Step-by-step instructions: 15 items
- +4Has examples (17 code blocks)
- +1License stated
Quality base 70; lint remarks subtract, signals add up to 100. Result: 75.