Ssl Cert Toolkit

SSL certificate toolkit

Use openssl on this host to inspect certificates, verify key/cert/CSR pairing, generate CSRs, convert common formats, and run simple validation.

Out of scope: cloud purchase/upload/deploy APIs, silently changing the system trust store, submitting CA requests for the user.

Rules

1. Clarify intent first: inspect / match / generate CSR / convert / verify—ask if unclear.
2. Confirm before writing files: confirm output paths; do not overwrite existing files unless asked.
3. Protect private keys: never paste key material into chat; suggest mode 0600; do not log key bodies.
4. Dependency: require openssl (command -v openssl). keytool only for JKS.
5. Stop when enough: after match/inspect succeeds, do not “optimize” unrelated files.
6. Fail closed on match: if OpenSSL cannot parse an input, report that—never treat empty digests as MATCH.

Capabilities

Inspect

openssl version
openssl x509 -in <cert.pem> -noout -subject -issuer -dates -ext subjectAltName 2>/dev/null
openssl x509 -in <cert.pem> -noout -text | head -80

For PFX, ask for the password; prefer -passin env:CERT_PASS over putting secrets on the command line:

openssl pkcs12 -in <file.pfx> -nokeys -clcerts -passin env:CERT_PASS

Match check (cert / key / CSR)

Compare public keys (preferred) or RSA moduli. Each openssl extract must succeed and produce non-empty output before comparing:

openssl x509 -in <cert.pem> -noout -pubkey | openssl md5
openssl pkey -in <key.pem> -pubout | openssl md5
openssl req -in <csr.pem> -noout -pubkey | openssl md5   # if CSR given

Parse failure or empty digest → not MATCH. Equal non-empty digests → MATCH.
Optional: openssl req -in <csr.pem> -noout -verify (CSR signature; separate from key match).

Generate CSR

Confirm CN/SAN, algorithm (default RSA 2048), and output directory.

openssl req -new -newkey rsa:2048 -nodes \
  -keyout <domain>.key -out <domain>.csr \
  -subj "/CN=<domain>"

openssl req -in <domain>.csr -noout -text | head -60

With SAN, write a temporary san.cnf (user confirms) then:

openssl req -new -newkey rsa:2048 -nodes \
  -keyout <domain>.key -out <domain>.csr \
  -config san.cnf -extensions v3_req

ECDSA:

openssl ecparam -genkey -name prime256v1 -out <domain>.key
openssl req -new -key <domain>.key -out <domain>.csr -subj "/CN=<domain>"

Remind: do not commit the private key; CSR can go to the CA.

Format conversion

Confirm inputs and target format first.

openssl pkcs12 -export -out <out.pfx> -inkey <key.pem> -in <cert.pem> [-certfile chain.pem]
openssl pkcs12 -in <in.pfx> -clcerts -nokeys -out cert.pem
openssl pkcs12 -in <in.pfx> -nocerts -nodes -out key.pem
openssl x509 -in <file> -noout -subject 2>/dev/null || openssl req -in <file> -noout -subject 2>/dev/null

Handle JKS only if the user asks and keytool exists; otherwise prefer PEM/PFX.

Simple verification

openssl x509 -in <cert.pem> -noout -checkend 0 && echo 'not expired' || echo 'expired or invalid'
openssl verify -CAfile <ca_or_chain.pem> <cert.pem>

Live site (read-only) when the user gives an HTTPS host:

echo | openssl s_client -connect <host>:443 -servername <host> 2>/dev/null | openssl x509 -noout -subject -dates

Output format

## Conclusion
What was done: inspect / match result / generated paths / conversion outputs.

## Evidence
- Relevant openssl output (redacted; no private key body)
- Digest comparison for match checks

## Recommendations
- Next steps (submit CSR, deploy where, `chmod 600`)
- Direction if expired or mismatched

Reply in the user's language.

Related skills

Example

User: Are server.crt and server.key a pair?

1. Confirm readable paths
2. Compare pubkey/modulus digests
3. Conclude MATCH or name the mismatch