Documenso Security Basics

What it does

When your agent uses it

• Securing API keys
• Configuring webhooks securely
• Implementing document security measures
• With phrases like documenso security

Example prompts

• “documenso security”
• “secure documenso”
• “documenso API key security”
• “/documenso-security-basics”

Requirements

• Python 3
• Docker
• A credential in DOCUMENSO_API_KEY
• A credential in DOCUMENSO_WEBHOOK_SECRET
• Compatibility (from SKILL.md): Designed for Claude Code
• Pre-approved tools (allowed-tools): Read, Write, Edit

Workflow steps

6 steps, taken from the step headings in SKILL.md.

1. 1API Key Security
2. 2Key Rotation with Zero Downtime
3. 3Webhook Secret Verification
4. 4Document Access Control
5. 5Signing Certificate Security (Self-Hosted)
6. 6Self-Hosted Production Secrets

What it can do on your machine

Read from SKILL.md and the folder at commit cfae287. It shows what the files ask for, not the result of running them.

• Tool permissions

  Pre-approves these tools, so the agent can use them without asking each time:

  • Read
  • Write
  • Edit

  From allowed-tools in the SKILL.md frontmatter.

• Runs code

  Shell commands in SKILL.md call:

  • openssl
  • docker

  From the folder's file list and the shell code blocks in SKILL.md.

• Network

  Links to these hosts (documentation or services it may open):

  • docs.documenso.com
  • owasp.org

  From URLs in SKILL.md, links to its own repository left out.

• Credentials

  Names these keys or tokens, usually read from environment variables:

  • DOCUMENSO_WEBHOOK_SECRET
  • DOCUMENSO_API_KEY
  • NEXTAUTH_SECRET
  • NEXT_PRIVATE_ENCRYPTION_KEY
  • NEXT_PRIVATE_ENCRYPTION_SECONDARY_KEY

  From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.

• Compatibility

  Designed for Claude Code

  From compatibility in the SKILL.md frontmatter.

Context cost

Documenso Security Basics loads about 1.7k tokens when it runs, and up to ~3.9k if it reads all its reference files. Until then it costs about 84 tokens; SKILL.md has 352 words of instructions outside code blocks.

Always · name and description, kept in context so the agent knows when to use it

~84

When it runs · the whole SKILL.md, loaded when a task matches

~1.7k

With references · SKILL.md plus every file in references/, read only if the agent opens them

~3.9k

Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.

Safety

• NoteMentions a .env fileSKILL.md:61

  - Store in `.env` (never committed) or a secrets manager (Vault, AWS Secrets Manager)

• NoteMentions a .env fileSKILL.md:68

  .env

• NoteMentions a .env fileSKILL.md:69

  .env.*

• NoteMentions a .env fileSKILL.md:178

  - [ ] `.env` in `.gitignore`

Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); files beside SKILL.md are not scanned.

SKILL.md

The full file from jeremylongshore/tons-of-skills-marketplace at commit cfae287, republished under its MIT licence (© jeremylongshore). 352 words, ~1,651 tokens.

name

documenso-security-basics

description

Implement security best practices for Documenso document signing integrations. Use when securing API keys, configuring webhooks securely, or implementing document security measures. Trigger with phrases like "documenso security", "secure documenso", "documenso API key security", "documenso webhook security".

allowed-tools

Read, Write, Edit

compatibility

Designed for Claude Code

version

1.14.0

license

MIT

author

Jeremy Longshore <jeremy@intentsolutions.io>

tags

saas, documenso, api, security, webhooks

// NEVER hardcode keys
const BAD = new Documenso({ apiKey: "api_abc123..." }); // Exposed in source

// ALWAYS use environment variables
const GOOD = new Documenso({ apiKey: process.env.DOCUMENSO_API_KEY! });

# .gitignore — always include
.env
.env.*
!.env.example

// Support dual keys during rotation
function getApiKey(): string {
  // Try primary first, fall back to secondary during rotation
  return process.env.DOCUMENSO_API_KEY_PRIMARY
    ?? process.env.DOCUMENSO_API_KEY_SECONDARY
    ?? (() => { throw new Error("No Documenso API key configured"); })();
}

// Rotation procedure:
// 1. Generate new key in Documenso dashboard
// 2. Set as DOCUMENSO_API_KEY_SECONDARY, deploy
// 3. Verify secondary key works
// 4. Move secondary to PRIMARY, deploy
// 5. Revoke old key in dashboard

import { timingSafeEqual } from "crypto";

function verifyWebhookSecret(req: Request): boolean {
  const received = req.headers["x-documenso-secret"] as string;
  const expected = process.env.DOCUMENSO_WEBHOOK_SECRET!;

  if (!received || !expected) return false;

  // Use constant-time comparison to prevent timing attacks
  return timingSafeEqual(
    Buffer.from(received, "utf8"),
    Buffer.from(expected, "utf8")
  );
}

# Python equivalent
import hmac, os
from flask import request

def verify_webhook(req):
    received = req.headers.get("X-Documenso-Secret", "")
    expected = os.environ["DOCUMENSO_WEBHOOK_SECRET"]
    return hmac.compare_digest(received, expected)

// Principle of least privilege with API keys
// Personal keys: only YOUR documents
// Team keys: all documents in the team

// Restrict document access by checking ownership
async function getDocumentSecure(documentId: number, userId: string) {
  const doc = await client.documents.getV0(documentId);

  // Verify the requesting user is the owner or a recipient
  const isOwner = doc.userId === parseInt(userId);
  const isRecipient = doc.recipients?.some(r => r.email === userEmail);

  if (!isOwner && !isRecipient) {
    throw new Error("Access denied: not authorized for this document");
  }

  return doc;
}

# Generate a self-signed certificate (development only)
openssl req -x509 -newkey rsa:4096 -keyout key.pem -out cert.pem -days 365 -nodes
openssl pkcs12 -export -out signing-cert.p12 -inkey key.pem -in cert.pem

# Mount into Docker container
docker run -v $(pwd)/signing-cert.p12:/opt/documenso/cert.p12 \
  -e NEXT_PRIVATE_SIGNING_LOCAL_FILE_PATH=/opt/documenso/cert.p12 \
  -e NEXT_PRIVATE_SIGNING_PASSPHRASE=your-passphrase \
  documenso/documenso:latest

# Generate cryptographically secure secrets
openssl rand -hex 32  # NEXTAUTH_SECRET
openssl rand -hex 32  # NEXT_PRIVATE_ENCRYPTION_KEY
openssl rand -hex 32  # NEXT_PRIVATE_ENCRYPTION_SECONDARY_KEY

# Never reuse secrets across environments
# Never use default values in production

© jeremylongshore, MIT. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file

Files

SKILL.md and 1 other file (references) in skills/.curated/documenso-security-basics of jeremylongshore/tons-of-skills-marketplace.

• SKILL.md
• references/implementation-guide.md

Open the folder on GitHubat commit cfae287