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openSSL Playground
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a_openssl_command_playground.md

OpenSSL Playground

Certificates

# human readable crt file
openssl x509 -in stackexchangecom.crt -text -noout

# human readable pem file
openssl x509 -in cert.pem -text -noout

# human readable cer file
openssl x509 -inform der -in foobar.cer -noout -text

# read part of certificate
openssl x509 -in foobar.crt -subject -serial -noout

# print Common Name and Serial Number
openssl x509 -in foobar.crt -subject -serial -noout | awk -F= '{print $NF}'

Verify Certificates

# Help
man verify

# Set path to certs to trust
export CERTS=/Users/{path_to_your_certs}

# Verify leaf - OK
openssl verify -CAfile ${CERTS}/local_rootca_2025.pem -untrusted ${CERTS}/local_intca_2023.pem ${CERTS}/local_leaf.pem

# Verify leaf - failed, as wrong Int CA
openssl verify -CAfile ${CERTS}/local_rootca_2025.pem -untrusted ${CERTS}/httpbin-org-IntCA.pem ${CERTS}/local_leaf.pem

# Verify Intermediate CA - OK
openssl verify -CAfile ${CERTS}/local_rootca_2025.pem ${CERTS}/local_intca_2023.pem

# Verify Intermediate CA ( with -no-CApath ) - OK
openssl verify -no-CApath -CAfile ${CERTS}/local_rootca_2025.pem ${CERTS}/local_intca_2023.pem

# Verify Intermediate CA - failed, as Int CA not signed by Root CA
openssl verify -CAfile ${CERTS}/local_rootca_2025.pem ${CERTS}/httpbin-org-IntCA.pem

# c_rehash
export CERTS=<path_to_your_certs>
c_rehash ${CERTS}

# Verify leaf_cert  ( Root CA and IntCA inside ${CERTS} )
openssl verify -CApath ${CERTS} ${UNTRUSTED}/local_leaf.pem

# Verify multiple untrusted
openssl verify -CApath ${CERTS} ${UNTRUSTED}/local_leaf.pem ${UNTRUSTED}/httpbin_org_leaf.pem

# Verify failure ( missing Int CA, unable to get local issuer certificate, error 20 )
openssl verify -CApath ${CERTS} ${UNTRUSTED}/local_leaf.pem

# Verify failure ( missing Root CA, error 2 at 1 depth lookup: unable to get issuer certificat )
openssl verify -CApath ${CERTS} ${UNTRUSTED}/local_leaf.pem

# Partial Chain flag
openssl verify -partial_chain -CApath ${CERTS} httpbin-org-leaf.pem

Verify Certificates ( real-time )

Overview of features

openssl help s_client

Set path to certs to folder of Certificates

export CERTS=/Users/{path_to_your_certs}

Run c_rehash

openssl/bin/c_rehash ${CERTS}

Partial chain allowed

openssl s_client -partial_chain -CApath ${CERTS} -connect httpbin.org:443

Print certificates in chain

openssl s_client -CApath ${CERTS} -connect httpbin.org:443 -showcerts | openssl x509 -text -noout

Quiet

openssl s_client -CApath ${CERTS} -connect httpbin.org:443 -quiet

TLS1.3 only

openssl s_client -CApath ${CERTS} -connect httpbin.org:443 -quiet -tls1_3

No TLS1.3 only

openssl s_client -CApath ${CERTS} -connect httpbin.org:443 -no_tls1_3

Set cipher

openssl s_client -CApath ${CERTS} -connect httpbin.org:443 -cipher ECDHE-RSA-AES128-GCM-SHA256

Debugging each step

openssl s_client -CApath ${CERTS} -state -nbio -connect httpbin.org:443

Generate RSA Private Key and Certificate

Generate RSA Private Key and Certificate ( with Private Key encryption )

openssl req -x509 -newkey rsa:2048 -keyout key.pem -out cert.pem -days 365

Generate RSA Private Key and Certificate ( without Private Key encryption )

openssl req -x509 -newkey rsa:2048 -keyout key.pem -nodes -out cert.pem -days 365

Create Certificate with existing Private Key

openssl req -key priv_1024.pem -new -x509 -days 365 -out domain.crt

Extract Public Key from Cert as PEM file

openssl x509 -pubkey -noout -in stackexchangecom.crt > pubkey.pem

Strip the Generic Header and Footer
awk '{if (NR!=9 && NR!=1) {print}}' pubkey.pem

MIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEAr0YDzscT5i6T2FaRsTGN
CiLB8OtPXu8N9iAyuaROh/nS0kRRsN8wUMk1TmgZhPuYM6oFS377V8W2LqhLBMrP
Xi7lnhvKt2DFWCyw38RrDbEsM5dzVGErmhux3F0QqcTI92zjVW61DmE7NSQLiR4y
onVpTpdAaO4jSPJxn8d+4p1sIlU2JGSk8LZSWFqaROc7KtXtlWP4HahNRZtdwvL5
dIEGGNWx+7B+XVAfY1ygc/UisldkA+a3D2+3WAtXgFZRZZ/1CWFjKWJNMAI6ZBAt
lbgSNgRYxdcdleIhPLCzkzWysfltfiBmsmgz6VCoFR4KgJo8Gd3MeTWojBthM10S
LwIDAQAB
Extract Public Key from Cert in Hex format
openssl x509 -modulus -noout < stackexchangecom.crt | sed s/Modulus=//

AF4603CEC713E62E93D85691B1318D0A22C1F0EB4F5EEF0DF62032B9A44E87F9D2D24451B0DF3050C9354E681984FB9833AA054B7EFB57C5B62EA84B04CACF5E2EE59E1BCAB760C5582CB0DFC46B0DB12C33977354612B9A1BB1DC5D10A9C4C8F76CE3556EB50E613B35240B891E32A275694E974068EE2348F2719FC77EE29D6C2255362464A4F0B652585A9A44E73B2AD5ED9563F81DA84D459B5DC2F2F974810618D5B1FBB07E5D501F635CA073F522B2576403E6B70F6FB7580B57805651659FF509616329624D30023A64102D95B812360458C5D71D95E2213CB0B39335B2B1F96D7E2066B26833E950A8151E0A809A3C19DDCC7935A88C1B61335D122F
Print public key
openssl rsa -inform PEM -pubin -in pubkey.pem -text -noout

Public-Key: (2048 bit)
Modulus:
    00:af:46:03:ce:c7:13:e6:2e:93:d8:56:91:b1:31:
    8d:0a:22:c1:f0:eb:4f:5e:ef:0d:f6:20:32:b9:a4:
    4e:87:f9:d2:d2:44:51:b0:df:30:50:c9:35:4e:68:
    19:84:fb:98:33:aa:05:4b:7e:fb:57:c5:b6:2e:a8:
    4b:04:ca:cf:5e:2e:e5:9e:1b:ca:b7:60:c5:58:2c:
    b0:df:c4:6b:0d:b1:2c:33:97:73:54:61:2b:9a:1b:
    b1:dc:5d:10:a9:c4:c8:f7:6c:e3:55:6e:b5:0e:61:
    3b:35:24:0b:89:1e:32:a2:75:69:4e:97:40:68:ee:
    23:48:f2:71:9f:c7:7e:e2:9d:6c:22:55:36:24:64:
    a4:f0:b6:52:58:5a:9a:44:e7:3b:2a:d5:ed:95:63:
    f8:1d:a8:4d:45:9b:5d:c2:f2:f9:74:81:06:18:d5:
    b1:fb:b0:7e:5d:50:1f:63:5c:a0:73:f5:22:b2:57:
    64:03:e6:b7:0f:6f:b7:58:0b:57:80:56:51:65:9f:
    f5:09:61:63:29:62:4d:30:02:3a:64:10:2d:95:b8:
    12:36:04:58:c5:d7:1d:95:e2:21:3c:b0:b3:93:35:
    b2:b1:f9:6d:7e:20:66:b2:68:33:e9:50:a8:15:1e:
    0a:80:9a:3c:19:dd:cc:79:35:a8:8c:1b:61:33:5d:
    12:2f
Exponent: 65537 (0x10001)

Keys

# generate 32-byte, base64 encoded key material
openssl rand -base64 32

RSA

Encrypt
echo 'Hi Alice!' | openssl rsautl -encrypt -pubin -oaep -inkey public_key.pem >message.bin

// The standard defines random padding with each encrypt API call
// https://en.wikipedia.org/wiki/Optimal_asymmetric_encryption_padding
// It is always padded to 256 characters, with 2048 key
Read ciphertext as Hex
xxd -ps -l 256 message.bin
Decrypt from binary ciphertext
openssl rsautl -decrypt -in message.bin -inkey private_key.pem -oaep
Decrypt and put plaintext in file
openssl rsautl -decrypt -in message.bin -inkey private.pem -oaep > plaintext.txt

AES

Encrypt
echo "foobar" | openssl enc -aes-256-cbc -base64 -pbkdf2
enter aes-256-cbc encryption password:alice
Verifying - enter aes-256-cbc encryption password:alice
U2FsdGVkX1/BRGpxGcBRBc/e9C6irJI53bh90HoLzP4=
Decrypt (AES)
echo "U2FsdGVkX1/BRGpxGcBRBc/e9C6irJI53bh90HoLzP4="  | openssl enc -base64 -d | openssl enc -aes-256-cbc -d -pbkdf2
enter aes-256-cbc decryption password:alice

// foobar

Key Pairs

openssl genrsa -out private.pem 2048   // add the -des3 flag to encrypt Private Key
openssl rsa -in private.pem -outform PEM -pubout -out public.pem // extract pub key
Convert private key file to PEM file
openssl pkcs12 -in mycaservercert.pfx -nodes -nocerts -out mycaservercertkey.pem
// you will be prompted for password
Print EC private key & extract public key
openssl ec -inform PEM -in private.pem -text -noout
openssl ec -in private.pem -pubout -out pubkey.pem
Read EC public key
cat pubkey.pem
openssl ec -inform PEM -pubin -in pubkey.pem -text -noout
Print RSA private key & extract public key
openssl rsa -inform PEM -in private.pem -text -noout
openssl rsa -in private.pem -pubout -out pubkey.pem

Helpers

Convert hex to binary

xxd -r -p message.hex message.bin

Convert hex -> base64 -> binary

cat enc_message.hex | base64 --decode > enc_message.bin

Convert binary -> base64 encoded data

openssl base64 -in message.bin -out b64message.txt

SHA1 Hash

openssl dgst -sha1 so_int_ca.pem

SHA256 Hash

openssl dgst -sha256 so_int_ca.pem

Verify downloaded file
cat openssl-1.1.1.tar.gz.sha256            // read the sent hash
openssl dgst -sha256 openssl-1.1.1.tar.gz  // generate a hash

Nginx Self-Signed Cert

Nginx needed the Leaf's Private Key the Leaf's Certificate or a certificate chain.

Whichever choice, I always found PEM files worked better with OpenSSL.

# Open KeyChain on macOS
# Right-click on Leaf cert
# Export the Certificate as a PEM file
# Verify
openssl x509 -noout -text -in eafCert.pem

SLOW
Export all Certs.
cat leaf_cert.pem > cert_chain.pem
cat int_ca_cert.pem >> cert_chain.pem
cat root_ca_cert.pem >> cert_chain.pem

If you hit Expecting: TRUSTED CERTIFICATE error, check you actually chained the Certificates and NOT the Public Keys.

Apply the new Leaf Private Key and Certificate Chain:

sudo nginx -s stop
sudo nginx

This all worked fine with Firefox and Safari on macOS. But Chrome gave: Error: "Subject Alternative Name Missing". Despite having a trusted Cert Chain (Root CA, Int CA), Chrome stopped the page loading.

To re-generate the files required by Nginx, I used the same Root CA, Int CA and focused on a new leaf that had a Subject Alternative Name. I used Keychain. See the picture below.

Reference

-Generating RSA Keys -<Extract Public Key as Hex -Certificate Signing Requests -Max size of RSA OAEP

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