cert-req

A simple Docker image to create certificate requests for web servers

Certificate operations via docker run

• (Optional) Build: docker build -t gunet/cert-req:latest .
• (Typical) Run: docker run --rm -e ORG=<ORG> -e SERVER=<hostname> -v $PWD/certs:/var/cert-req/certs gunet/cert-req <argument>
• Example: docker run --rm -e ORG=sch.gr -e SERVER=sso-01-test.sch.gr -v $PWD/certs:/var/cert-req/certs gunet/cert-req create
• If we want to pass the passphrase in stdin then we need to add the -it option.
• Files (certificates, private keys, CSRs etc) will be in folder $PWD/certs
• Possible arguments
  • create: Create a new private key and server.csr
  • print: Print CSR
  • renew: Regenerate the CSR reusing the same key
  • encrypt: Encrypt the private key with a pass phrase
  • decrypt: Remove the passphrase from an encrypted key
  • encrypt-file: Encrypt the file provided in the FILE environment variable with the PASSPHRASE (or we will request it) with symmetrical encryption. The resulting file will get a .aes extension
  • decrypt-file: Decrypt the file with symmetrical encryption. For the output file we remove the .aes extension. If it does not exist, we fail.
  • self-sign: Create a new private key and CSR and self-sign the certificate.
  • self-sign-ca: Create a CA, a private key and CSR and self-sign a certificate. The certs/ folder will include the CSR and private key.
  • resign-ca: Re-sign the server certificate using the existing CA.
  • dh: Create a dh.pem DH parameters file
• Passphrase:
  • Generally, the passphrase will be requested.
  • If an environment variable called PASSPHRASE is present then that will be used
  • If the environment variable is present and the command is self-sign or self-sign-ca then we will use it to encrypt the private key as well.
• Filenames:
  • Certificate: server.crt
  • CSR: server.csr
  • Private key (no passphrase): privkey.pem
  • Private key (encrypted with passphrase): privkey.key

docker-compose

• Build: docker-compose build
• Run: docker-compose run -e ORG=<ORG> -e SERVER=<hostname> --rm cert-req <command>
• CSR and private key will be in $PWD/certs

Environment Variables

• ORG: Organization (ie GUNET)
• SERVER: The server DNS name
• PASSPHRASE: The passphrase to use when encryting/decrypting. If it is not passed as an environment variable, it will be requested (you need to pass -it option in this case)
• SUBJALTNAMES: A comma separated list of subAltNames to be included in the certificate request/self-signed certificate.
• FILE: The (absolute) path (in the container context) for a file to be encrypted or decrypted

Image size

• gunet/cert-req: 82.5MB
  • debian:bullseye-slm: 80.5MB

Process

• Create certificate request with new key: openssl req -new -newkey rsa:4096 -nodes -keyout privkey.pem -out server.csr -config server.cnf -batch
• Create a self-signed certificate with new key: openssl req -x509 -newkey rsa:4096 -nodes -keyout privkey.pem -out server.csr -config server.cnd -sha256 -days 7300 -batch
• Self-sign a certificate using an already existing CSR and private key: openssl req -x509 -in server.csr -config server.cnf -key privkey.pem -out server.crt -days 7300 -sha256 -batch
• Renew certificate request reusing key: openssl req -new -key certs/privkey.pem -out certs/server.csr -config server.cnf -batch
• Print CSR: openssl req -text -noout -verify -in certs/server.csr

Private Keys

• Check if a private key is encrypted or not: openssl rsa -text -noout -in <name of key>.key
• Encrypt a private key or change the passphrase: openssl rsa -aes256 -passout PASS -in <unencrypted name> -out <encrypted name>
  • Note: Some algorithms like des are not supported by default by OpenSSL v3.0 and should not be used
• Remove the passphrase: openssl rsa -in <encrypted name> -out <unencrypted name>
• Remove the passphrase (passing the passphrase): openssl rsa -passin PASS -in <encrypted named> -out <unencrypted name>
• It is usually recommended to have the unencrypted private key end in .pem and the encrypted in .key
• Symmetrical encryption on a file (passphrase in env variable):
  • Encrypt: openssl enc -aes-256-cbc -md sha512 -pbkdf2 -iter 100000 -salt -pass PASS -in <unencrypted> -out <encrypted>
  • Decrypt: openssl enc -aes-256-cbc -md sha512 -pbkdf2 -iter 100000 -salt -d -pass PASS -in <encrypted> -out <unencrypted>
• PASS can be one of:
  • pass:${PASS}: A text passphrase
  • env:PASS: The passphrase will take the value of the environment variable PASS

DH Params

• Create a DH params file (4096 bits length): openssl dhparam -out certs/dh.pem 4096

Print Certificate

• Print certificate: openssl x509 -text -in server.crt
• Print a certificate which is stored in DER format (usually certificates taken from an Authority Information Access endpoint): openssl x509 -text -inform der -in <cert-file>
• Print certificate chain: openssl crl2pkcs7 -nocrl -certfile server.crt | openssl pkcs7 -print_certs -noout
• Print md5 checksums:
  • For certificate: openssl x509 -noout -modulus -in server.crt| openssl md5
  • For key: openssl rsa -noout -modulus -in privkey.pem| openssl md5
  • For CSR: openssl req -noout -modulus -in server.csr| openssl md5
• Expiration:
  • Show expiration: openssl x509 -noout -enddate -in server.crt
  • Show all dates: openssl x509 -noout -dates -in server.crt
  • Check expiration: openssl x509 -noout -checkend <seconds> -in server.crt

crt.sh

• crt.sh is a tool to check/download Sectigo certificates online
• Return a JSON strcture with non-expired leaf certificates for a specific domain: https://crt.sh/?Identity=<domaain>&exclude=expired&deduplicate=Y&output=json

OpenSSL connect

• We can use openssl s_client to directly connect to a server and check the TLS protocol
• The usual run is: openssl s_client -connect <name>:443
• To quit just after TLS connection establishment: time echo "Q" | openssl s_client -connect <name>:443 2>1 >/dev/null
• If we add the -servername argument then openssl also does SNI

Test HTTPS web

• Use the -quiet and the -crlf options
• Example:

# openssl s_client -connect sso.asfa.gr:443 -quiet -crlf
GET /login HTTP/1.1
Host: sso.asfa.gr

Testing SMTP (StartTLS)

• Reference
• Connect to an SMTP server with StartTLS: openssl s_client -quiet -connect relay.grnet.gr:587 -starttls smtp
• The -quiet flag is important in order to be able to issue capitalized SMTP commands with no problem.
• Total test:

# openssl s_client -quiet -connect relay.grnet.gr:587 -starttls smtp
depth=2 C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST Network, CN = USERTrust RSA Certification Authority
verify return:1
depth=1 C = NL, O = GEANT Vereniging, CN = GEANT OV RSA CA 4
verify return:1
depth=0 C = GR, ST = Attik\C3\AD, O = National Infrastructures for Research and Technology, CN = relay.grnet.gr
verify return:1
250 HELP
MAIL FROM: <[email protected]>
250 OK
RCPT TO: <[email protected]>
250 Accepted
DATA
354 Enter message, ending with "." on a line by itself
Subject: Test
test
.
250 OK id=1q6SbR-0007fb-Tr
QUIT
221 relay.grnet.gr closing connection

• Test SMTP auth:

# echo -n "username" | base64
dXNlcm5hbWU=
# echo -n "password" | base64
cGFzc3dvcmQ=

(cut)
250 8BITMIME
AUTH LOGIN
334 VXNlcm5hbWU6
dXNlcm5hbWU=
334 UGFzc3dvcmQ6
cGFzc3dvcmQ=
235 2.7.0 Authentication successful

Test SSL

• The testssl.sh can run a set of SSL/TLS tests against a server. A Docker image is available
• The simpe run is docker run --rm -ti drwetter/testssl.sh <host>[:<port>]

OpenSSL Timer

• OpenSSL also provides an option to time SSL connections for a server: openssl s_time -connect <host>:<port>

Performance

• Reference: OpenVPN Cookbook 2nd edition, Chpt. 8
• Modern CPUs have the AES-NI instruction set which speeds up encryption
• You can run openssl speed test with:
  • openssl speed -evp aes-256-gcm to test the AES-256-GCM cipher family
  • openssl speed -evp aes-256-cbc to test the AES-256-CBC cipher family
  • Use the OPENSSL_ia32cap=0 environment variable to disable the AES-NI instruction set