Reading "TLS Mastery" by Michael W Lucas.

I have read "TLS Mastery" by Michael W Lucas.

It is not a bad introduction into openssl and TLS, but I feel that his book on SSH is better.

1. Review

So, I found that I had to read an introduction into TLS when I failed to generate a self-signed certificate for a simple setup at work, which needed a few TLS certificates to place a stupid piece of software which refused to work without them.

The system was completely closed-circuit, none of that stuff was required or even beneficial for my use-case, but since Open Source is obsessed with cryptomania and is extremely keen on embedding it into everything which falls into their hands, I thought that it is worth learning a few bits.

I had already known that Lucas is good at reading man pages aloud (or rather rewriting their dry and terse language into something much more palatable, having a structure and a narrative), I resorted to reading his book "TLS Mastery".

What can I say? It is not a bad book, but I am feeling that it over-complicates things.

It is true that TLS is over-complicated by design, and Lucas actually does a decent job introducing the needless but unavoidable complexities, I am feeling that he buys into the TLS complexity too much, taking it at face value and not simplifying where it is possible to simplify things.

On the other hand, I am writing this from a position of someone who has already spent time on fighting with TLS certificates for some time.

The books essentially consists of four parts:

Introducing TLS, vocabulary, and notation.
Describing keypair generation and those few cryptography parameters which might be of use for a practitioner.
Getting certificates signed by an automated service like Let's Encrypt.
Running one's own Certificate Authority, which is not an organisation, but a set of scripts.

The last part is introduced in great detail, and describes every step of this potentially overbearing process, but does not give a few "simple and straightforward" commands to plug into your script and placate the pesky software which just needs encryption for whatever reason.

Anyway, the last part of 2 in this file gives one for you.

In any case, the book is short, the language is lively and rich with metaphors, so it is a fun read anyway.

The language is, maybe, even a little bit too simple and approachable, for me, but this is not necessarily bad, because nowadays everyone has to be a little bit of a sysadmin, even though for most of us it is not an activity of choice but an unfortunate necessity, and therefore treating us all as ignorant newbies is a good thing, not bad.

2. Notes

2.1. References

2.2. Simple request

openssh s_client is a TLS-aware telnet/netcat, similar to stunnel

openssl s_client -showcerts -connect www.baidu.com:443 <<EOF
GET / HTTP/1.1
EOF

2.3. Understanding the crypto system

2.3.1. HMAC

HMAC is essentially a signature. Hash-based Message Authentication Code. Message -> hash(message) -> privkey_enc(hash(message)) -> short signature/hmac

check correct if hash(message)==pubkey_dec(hmac)

But there may be other methods to generate the HMAC

Again, they are used during stream exchange to encrypt every block, not during key exchange (even though key exchange needs a signature too).

2.3.2. Algorithms

Key Exchange
```
openssl ciphers -v 'ALL:COMPLEMENTOFALL' | awk '{print $3;}' | sort | uniq
```
Kx=DH Kx=DHEPSK Kx=ECDH Kx=ECDHEPSK Kx=PSK Kx=RSA Kx=RSAPSK Kx=any Kx=SRP

https://openssl-users.openssl.narkive.com/N0eGKnwY/ecdh-vs-ecdhe
1. ECDHE :: Elliptic Curve Diffie Hellman Ephemeral (no, the last E is NOT "Exchange")
2. ECDHEPSK :: Not sure, I think it is ECDHE, but with some unfair optimisations
3. ECDH :: Elliptic Curve Diffie Hellman (same key persists over the session)
4. RSA :: Rivest Shamir Adleman
5. RSAPSK :: -//-
6. DH :: Diffie Hellman (not Elliptic)
7. DHE :: Diffie Hellman Ephemeral
8. DHEPSK :: -//-
9. SRP :: Some obscure stuff from 1997 "Secure Remote Password protocol (SRP) is an augmented password-authenticated key exchange (PAKE) protocol"
Surprisingly, Curve25519 is missing.
Authentication
```
openssl ciphers -v 'ALL:COMPLEMENTOFALL' | awk '{print $4;}' | sort | uniq
```
Au=DSS Au=ECDSA Au=None Au=PSK Au=RSA Au=any
1. ECDSA :: Elliptic Curve Digital Signature Algorithm
2. RSA :: -//-
3. DSA :: -//-, 1991
Missing ciphers o_O?
1. EdDSA :: Edwards' DSA, why is it missing?
Symmetric Encryption with Method
```
openssl ciphers -v 'ALL:COMPLEMENTOFALL' | awk '{print $5;}' | sort | uniq
```
Enc=AES(128) Enc=AES(256) Enc=AESCCM(128) Enc=AESCCM(256) Enc=AESCCM8(128) Enc=AESCCM8(256) Enc=AESGCM(128) Enc=AESGCM(256) Enc=ARIAGCM(128) Enc=ARIAGCM(256) Enc=CHACHA20/POLY1305(256) Enc=Camellia(128) Enc=Camellia(256) Enc=IDEA(128) Enc=None Enc=SEED(128)
1. AES :: Rijndael 2002, a "new" standard when DES was broken.
2. ARIA :: South Korean AES 2003
3. ChaCha20-Poly1305 :: Bernstein's cipher from 2005/2008, ChaCha20 works only in AEAD with Poly1305, I don't know why
4. Camellia :: NTT/Mitsubishi candidate for AES, 2000
5. IDEA :: 1991, First replacement for DES
6. SEED :: South Korean cipher from 1998
Missing
1. Deprecated DES/3DES :: Digital Encryption Standard, 56 bit
2. Deprecated RC2 :: 1987, Rivest Cipher 2
3. Deprecated RC4 :: 1987, Rivest Cipher 4 40-2048 bits, nowadays seldom used
4. Salsa20
5. XChaCha20
Methods are extensively covered in Bruce Schneier's book.
1. CBC :: Cipher block chaining https://en.wikipedia.org/wiki/Block_cipher_mode_of_operation#CBC
2. CCM :: Counter with cipher block chaining message authentication code
3. CCM_8 :: CCM with different authentication tag, 8 bytes (not bits)
4. GCM :: Galois Counter Mode
Message Authentication Code (MAC, Hash-based MAC (HMAC))
```
openssl ciphers -v 'ALL:COMPLEMENTOFALL' | awk '{print $6;}' | sort | uniq
```
Mac=AEAD Mac=MD5 Mac=SHA1 Mac=SHA256 Mac=SHA384

AEAD is not a separate algorithm, it means that Message Authentication is built into encryption.
```
openssl ciphers -v  | grep -F 1.3
```
TLS_AES_256_GCM_SHA384 TLSv1.3 Kx=any Au=any Enc=AESGCM(256) Mac=AEAD TLS_CHACHA20_POLY1305_SHA256 TLSv1.3 Kx=any Au=any Enc=CHACHA20/POLY1305(256) Mac=AEAD TLS_AES_128_GCM_SHA256 TLSv1.3 Kx=any Au=any Enc=AESGCM(128) Mac=AEAD

The suffix is SHA256, but Mac=AEAD. facepalm

2.3.3. Perfect Forward Secrecy

Inability to decrypt a full session dump even if a key is recovered later.

2.4. File formats

2.4.1. Serialisation

ASN.1 and OID.

ASN.1 is used for encoding:

X.500 directory structure
X.509 (TLS and similar) certificates
LDAP
SNMP

Not sure if it is much better than protobuf, but this is a decision taken years ago.

ASN.1 is a syntactic notation, and needs a "lexical syntax" encoding.

DER :: Distinguished Encoding Rules, a binary format for ASN.1
PEM :: Privacy-Enanced Mail, a text format for ASN.1, headers+base64(der)
pkcs12 :: usually cert+key+chain in one file, with .p12 ext

2.4.2. Working with keys

openssl rsa :: working with rsa keys
openssl ec :: working with elliptic curves, dsa keys
openssl x509 :: working with x509 certs
openssl pkcs12 :: working with pkcs12 cert archives

Funny, if you give openssl a "bundle", a lump of certificates, it only processes the first one, but gnutls (certtool) processes all of them.

How to save a website cert and chain into a file?

openssl s_client -connect www.baidu.com:443 -showcerts </dev/null 2>/dev/null | openssl x509 -outform PEM > file.pem

openssl s_client -showcerts -connect www.rabobank.nl:443 </dev/null 2>/dev/null | openssl x509 -noout -text

Certificate:
    Data:
        Version: 3 (0x2)
        Serial Number:
            39:0f:97:a1:9b:b1:9a:2d:d6:10:b9:82:df:f7:23:b6
        Signature Algorithm: ecdsa-with-SHA256
        Issuer: C = GB, ST = Greater Manchester, L = Salford, O = Sectigo Limited, CN = Sectigo ECC Extended Validation Secure Server CA
        Validity
            Not Before: Apr  1 00:00:00 2025 GMT
            Not After : Apr  1 23:59:59 2026 GMT
        Subject: serialNumber = 30046259, jurisdictionC = NL, businessCategory = Private Organization, C = NL, ST = Utrecht, O = Cooperatieve Rabobank U.A., CN = rabobank.nl
        Subject Public Key Info:
            Public Key Algorithm: id-ecPublicKey
                Public-Key: (256 bit)
                pub:
                    04:fa:72:7e:f6:30:8f:ad:f4:5e:d7:47:05:35:5a:
                    ae:cf:63:4b:4e:4c:4b:8f:f6:e6:c2:93:6c:bf:61:
                    7e:4c:a1:71:2d:5a:c5:0d:49:bc:4d:c5:be:5b:33:
                    03:26:7c:de:b3:37:6b:bd:9b:47:be:65:94:df:bb:
                    9e:d1:e2:fb:b1
                ASN1 OID: prime256v1
                NIST CURVE: P-256
        X509v3 extensions:
            X509v3 Authority Key Identifier: 
                keyid:EF:C1:2A:95:0C:32:DA:FB:73:30:DC:8A:13:D8:15:4B:F7:13:E8:F8

            X509v3 Subject Key Identifier: 
                2A:F2:1C:C8:05:79:FA:45:42:12:5B:77:64:3A:21:15:A8:CC:32:A5
            X509v3 Key Usage: critical
                Digital Signature
            X509v3 Basic Constraints: critical
                CA:FALSE
            X509v3 Extended Key Usage: 
                TLS Web Server Authentication, TLS Web Client Authentication
            X509v3 Certificate Policies: 
                Policy: 1.3.6.1.4.1.6449.1.2.1.5.1
                  CPS: https://sectigo.com/CPS
                Policy: 2.23.140.1.1

            X509v3 CRL Distribution Points: 

                Full Name:
                  URI:http://crl.sectigo.com/SectigoECCExtendedValidationSecureServerCA.crl

            Authority Information Access: 
                CA Issuers - URI:http://crt.sectigo.com/SectigoECCExtendedValidationSecureServerCA.crt
                OCSP - URI:http://ocsp.sectigo.com

            CT Precertificate SCTs: 
                Signed Certificate Timestamp:
                    Version   : v1 (0x0)
                    Log ID    : 96:97:64:BF:55:58:97:AD:F7:43:87:68:37:08:42:77:
                                E9:F0:3A:D5:F6:A4:F3:36:6E:46:A4:3F:0F:CA:A9:C6
                    Timestamp : Apr  1 13:36:49.891 2025 GMT
                    Extensions: none
                    Signature : ecdsa-with-SHA256
                                30:44:02:20:2E:80:F4:58:61:1D:DF:B7:BB:0F:AA:B7:
                                4C:A3:B8:F7:4C:E2:F2:D1:73:CE:2A:26:42:F7:83:93:
                                42:35:72:F1:02:20:6E:A0:4B:FA:72:3D:EB:55:F3:8A:
                                F8:97:7C:B1:E4:A3:AD:33:9C:21:25:DA:14:48:A5:9B:
                                7D:C7:E4:78:9D:11
                Signed Certificate Timestamp:
                    Version   : v1 (0x0)
                    Log ID    : 19:86:D4:C7:28:AA:6F:FE:BA:03:6F:78:2A:4D:01:91:
                                AA:CE:2D:72:31:0F:AE:CE:5D:70:41:2D:25:4C:C7:D4
                    Timestamp : Apr  1 13:36:49.859 2025 GMT
                    Extensions: none
                    Signature : ecdsa-with-SHA256
                                30:45:02:20:2C:C5:F2:D4:94:D0:44:7D:48:BA:27:C0:
                                44:2E:6A:57:01:16:4F:5B:54:A7:65:B9:44:4F:D5:BA:
                                2B:78:03:9A:02:21:00:8E:EC:5C:3F:32:08:E2:0C:DC:
                                7C:FE:53:E1:F1:2F:1A:D4:78:18:40:83:4F:31:26:99:
                                D3:3B:2B:B6:68:31:FC
                Signed Certificate Timestamp:
                    Version   : v1 (0x0)
                    Log ID    : 0E:57:94:BC:F3:AE:A9:3E:33:1B:2C:99:07:B3:F7:90:
                                DF:9B:C2:3D:71:32:25:DD:21:A9:25:AC:61:C5:4E:21
                    Timestamp : Apr  1 13:36:49.889 2025 GMT
                    Extensions: none
                    Signature : ecdsa-with-SHA256
                                30:45:02:21:00:D1:3C:38:FB:A8:A4:21:72:36:92:C2:
                                D1:EA:14:98:94:FA:C1:79:67:60:CD:4C:95:77:AC:10:
                                4F:BB:C2:95:31:02:20:47:39:49:5E:C2:46:CB:BC:97:
                                FE:97:2F:B3:81:44:1C:D7:A8:1D:13:BE:2F:E4:6E:EF:
                                92:E4:53:1A:94:44:A2
            X509v3 Subject Alternative Name: 
                DNS:rabobank.nl, DNS:www.rabobank.nl
    Signature Algorithm: ecdsa-with-SHA256
         30:44:02:20:1e:00:23:53:80:75:3f:19:f4:38:8f:00:bb:6a:
         5f:f2:27:db:56:2e:ca:4c:d3:96:40:84:08:4d:11:aa:b0:f7:
         02:20:43:0e:64:a1:63:37:6b:14:26:ce:a5:91:14:36:72:50:
         3e:fe:35:8e:4f:d5:43:c0:fd:ae:b5:66:8c:ec:fa:72

The above is an Extended Validation certificate, which has not just a domain name in the Subject, but the country and the business name.

2.5. Signing and Encryption

We do not use Public Key Encryption any more.

We use Public Key Signing, and apply it to obtaining Symmetric Encryption Keys using Diffie-Hellman.

So even if your certificate is invalid for signing, it does not mean that the key is not good for organising an encrypted communication link. (It probably does not work for asynchronous encryption, such as email or ordinary mail.)

2.6. Revocation

openssl crl

curl 'http://crl.sectigo.com/SectigoECCExtendedValidationSecureServerCA.crl' | openssl  crl -inform DER -noout -text

Certificate Revocation List (CRL):
        Version 2 (0x1)
        Signature Algorithm: ecdsa-with-SHA256
        Issuer: C = GB, ST = Greater Manchester, L = Salford, O = Sectigo Limited, CN = Sectigo ECC Extended Validation Secure Server CA
        Last Update: May 22 13:01:18 2025 GMT
        Next Update: May 29 13:01:18 2025 GMT
        CRL extensions:
            X509v3 Authority Key Identifier: 
                keyid:EF:C1:2A:95:0C:32:DA:FB:73:30:DC:8A:13:D8:15:4B:F7:13:E8:F8

            X509v3 CRL Number: 
                2461
Revoked Certificates:
    Serial Number: F68D62FBF1623665C9CCD6C71A5549DE
        Revocation Date: Jun 10 15:00:25 2024 GMT
    Serial Number: 054D37B37752D9AE48F5292AFB1AD799
        Revocation Date: Sep  9 12:52:04 2024 GMT
    Serial Number: 7FC8A4C765F72B86725390B2D79F4E5B
        Revocation Date: Sep 25 13:35:00 2024 GMT
        CRL entry extensions:
            X509v3 CRL Reason Code: 
                Superseded
    Serial Number: 50E07CD40E1358AC8AA8EA336D365833
        Revocation Date: Oct  1 23:55:55 2024 GMT
    Serial Number: 7BD6D2B8666F79C9022CCDE3FA26839D
        Revocation Date: Oct  1 23:55:56 2024 GMT
    Serial Number: 9BC21C5B7E1D909B9E3F9ADFC4DA0DF3
        Revocation Date: Oct  4 13:37:30 2024 GMT
    Serial Number: B671F7363552EDAA2EC68D4A5852AD15
        Revocation Date: Oct 21 12:22:24 2024 GMT
    Serial Number: 5AB252C6DB13A335E40CA6E10985A7AB
        Revocation Date: Oct 22 09:24:52 2024 GMT
    Serial Number: 085A9DC7B48A82CB52BCFC2E99628979
        Revocation Date: Oct 23 11:43:24 2024 GMT
    Serial Number: B7321C7A2C5CCF8DE73E982BA44748C1
        Revocation Date: Feb 21 14:12:52 2025 GMT
    Serial Number: 35641F6F81DC2639A810DC1A53AF04F4
        Revocation Date: Mar  5 19:24:59 2025 GMT
        CRL entry extensions:
            X509v3 CRL Reason Code: 
                Superseded
    Serial Number: 21927D6ADA83B7617F367BE59798976E
        Revocation Date: Mar  5 19:25:19 2025 GMT
        CRL entry extensions:
            X509v3 CRL Reason Code: 
                Superseded
    Serial Number: 3606E08FFCAF6E809BAB0632C6722A73
        Revocation Date: Mar  5 19:25:43 2025 GMT
        CRL entry extensions:
            X509v3 CRL Reason Code: 
                Superseded
    Serial Number: 6D305EA71C9749936EBE6082F0A7F555
        Revocation Date: Mar 27 09:48:55 2025 GMT
    Serial Number: B80F154F16A648C32F9D218B14A5724C
        Revocation Date: Mar 31 18:53:03 2025 GMT
    Serial Number: 9BE747179EA0A5898DA46AC68E89D2E4
        Revocation Date: Apr 16 13:23:21 2025 GMT
    Serial Number: 6E5BE0F63B29A51737DA8C1DD9F88D40
        Revocation Date: Apr 17 22:05:17 2025 GMT
        CRL entry extensions:
            X509v3 CRL Reason Code: 
                Cessation Of Operation
    Serial Number: 6D2A42743E9A0BEAA26E227A550AB29C
        Revocation Date: Apr 28 14:41:52 2025 GMT
        CRL entry extensions:
            X509v3 CRL Reason Code: 
                Cessation Of Operation
    Signature Algorithm: ecdsa-with-SHA256
         30:44:02:20:75:78:f1:55:ee:6b:5e:06:5c:cf:fd:1f:3b:ce:
         7e:c8:0a:bb:44:44:02:12:37:11:85:5d:9c:41:be:f2:65:ae:
         02:20:6d:13:bc:00:b4:58:31:85:9e:14:10:0f:e3:32:6e:62:
         85:6a:7f:57:6a:9d:b2:af:bd:96:86:fd:7b:4f:a1:1c

2.7. Negotiation

openssl s_client -crlf -tls1_2 -connect baidu.com:443 </dev/null 2>&1

depth=2 C = US, O = DigiCert Inc, OU = www.digicert.com, CN = DigiCert Global Root G2
verify return:1
depth=1 C = US, O = "DigiCert, Inc.", CN = DigiCert Secure Site Pro G2 TLS CN RSA4096 SHA256 2022 CA1
verify return:1
depth=0 C = CN, ST = \E5\8C\97\E4\BA\AC\E5\B8\82, O = "BeiJing Baidu Netcom Science Technology Co., Ltd", CN = www.baidu.cn
verify return:1
CONNECTED(00000008)
---
Certificate chain
 0 s:C = CN, ST = \E5\8C\97\E4\BA\AC\E5\B8\82, O = "BeiJing Baidu Netcom Science Technology Co., Ltd", CN = www.baidu.cn
   i:C = US, O = "DigiCert, Inc.", CN = DigiCert Secure Site Pro G2 TLS CN RSA4096 SHA256 2022 CA1
 1 s:C = US, O = "DigiCert, Inc.", CN = DigiCert Secure Site Pro G2 TLS CN RSA4096 SHA256 2022 CA1
   i:C = US, O = DigiCert Inc, OU = www.digicert.com, CN = DigiCert Global Root G2
 2 s:C = US, O = DigiCert Inc, OU = www.digicert.com, CN = DigiCert Global Root G2
   i:C = US, O = DigiCert Inc, OU = www.digicert.com, CN = DigiCert Global Root CA
---
Server certificate
-----BEGIN CERTIFICATE-----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FkKMSOAFL1Fi82T53fEaAHYASZybad4dfOz8Nt7Nh2SmuFuvCoeAGdFVUvvp6ynd
+MMAAAGU+RfNOQAABAMARzBFAiBf0Fj9+VSVmJIvrjVeSa/Jppcrw52PvqWOQaRS
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79ciq5i7ls8IId2SNzcJ6r/SqN03ukj3oOUC0Y3r+whc7f28H5jK/uf/0g==
-----END CERTIFICATE-----
subject=C = CN, ST = \E5\8C\97\E4\BA\AC\E5\B8\82, O = "BeiJing Baidu Netcom Science Technology Co., Ltd", CN = www.baidu.cn

issuer=C = US, O = "DigiCert, Inc.", CN = DigiCert Secure Site Pro G2 TLS CN RSA4096 SHA256 2022 CA1

---
No client certificate CA names sent
Peer signing digest: SHA512
Peer signature type: RSA
Server Temp Key: ECDH, P-256, 256 bits
---
SSL handshake has read 5531 bytes and written 338 bytes
Verification: OK
---
New, TLSv1.2, Cipher is ECDHE-RSA-AES128-GCM-SHA256
Server public key is 2048 bit
Secure Renegotiation IS supported
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : ECDHE-RSA-AES128-GCM-SHA256
    Session-ID: 8528DF68F938AD4BDFBB93769E99CB39D10D5F6052DD606D0C3C32BCA0152D45
    Session-ID-ctx: 
    Master-Key: BB69A85A7F9DB25C7C8FE1BB68D33D5987CE4F7BCBD321189485952B396E5994CE35DC49BD5A2E0CA19C5B1436499705
    PSK identity: None
    PSK identity hint: None
    TLS session ticket lifetime hint: 72000 (seconds)
    TLS session ticket:
    0000 - f3 5a 68 38 69 0a 42 7e-86 4a ba 21 56 60 9a 0e   .Zh8i.B~.J.!V`..
    0010 - 62 0c f2 2e e4 cb 47 98-2d 24 92 9f c0 a6 65 a2   b.....G.-$....e.
    0020 - b6 2b 0c cf bc c5 0b 58-d9 77 88 6e 84 f0 0e dd   .+.....X.w.n....
    0030 - 55 a0 3c 88 37 d2 af 93-aa e1 3a c6 74 0d 42 19   U.<.7.....:.t.B.
    0040 - e1 a8 11 29 85 47 82 d5-1b 2b 4d d1 98 50 fb e5   ...).G...+M..P..
    0050 - c3 b0 5a 6d f3 c2 eb 61-2e 77 05 e4 70 b6 53 66   ..Zm...a.w..p.Sf
    0060 - fd 6c 53 0e f0 56 a1 27-90 49 c0 ca 3a 3c 3e b5   .lS..V.'.I..:<>.
    0070 - b7 58 6a f6 ac 25 4b 97-82 28 6c d0 0b 8f 4f 85   .Xj..%K..(l...O.
    0080 - 4b be 10 76 f7 6e 32 4d-f3 0b 33 d9 8c 8b fd de   K..v.n2M..3.....
    0090 - a1 61 2e 76 8c 7f 49 e7-5b a2 cc 60 44 99 eb 02   .a.v..I.[..`D...
    00a0 - 43 4f fe b8 5d a1 5b 8c-27 fc 15 1f b9 af 4d 6a   CO..].[.'.....Mj

    Start Time: 1747984221
    Timeout   : 7200 (sec)
    Verify return code: 0 (ok)
    Extended master secret: no
---
DONE

openssl s_client -crlf -connect microsoft.com:443 </dev/null 2>&1

depth=2 C = US, O = DigiCert Inc, OU = www.digicert.com, CN = DigiCert Global Root G2
verify return:1
depth=1 C = US, O = Microsoft Corporation, CN = Microsoft Azure RSA TLS Issuing CA 07
verify return:1
depth=0 C = US, ST = WA, L = Redmond, O = Microsoft Corporation, CN = microsoft.com
verify return:1
CONNECTED(00000008)
---
Certificate chain
 0 s:C = US, ST = WA, L = Redmond, O = Microsoft Corporation, CN = microsoft.com
   i:C = US, O = Microsoft Corporation, CN = Microsoft Azure RSA TLS Issuing CA 07
 1 s:C = US, O = Microsoft Corporation, CN = Microsoft Azure RSA TLS Issuing CA 07
   i:C = US, O = DigiCert Inc, OU = www.digicert.com, CN = DigiCert Global Root G2
---
Server certificate
-----BEGIN CERTIFICATE-----
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yOI=
-----END CERTIFICATE-----
subject=C = US, ST = WA, L = Redmond, O = Microsoft Corporation, CN = microsoft.com

issuer=C = US, O = Microsoft Corporation, CN = Microsoft Azure RSA TLS Issuing CA 07

---
No client certificate CA names sent
Peer signing digest: SHA256
Peer signature type: RSA-PSS
Server Temp Key: X25519, 253 bits
---
SSL handshake has read 8147 bytes and written 379 bytes
Verification: OK
---
New, TLSv1.3, Cipher is TLS_AES_128_GCM_SHA256
Server public key is 2048 bit
Secure Renegotiation IS NOT supported
No ALPN negotiated
Early data was not sent
Verify return code: 0 (ok)
---
DONE

Master-Key should be an AES key.

TLS has a feature for PSK (pre-shared key), which is almost never used.

TLS has a feature for passwords (SRP), and I have also not seen it being used.

2.8. Making CSR

[ req ] # necessary ?
prompt = no # no interactive
default_keyfile = my-server.net.key
distinguished_name = req_distinguished_name # refers to a section name
req_extensions = v3_req # also section name

[ req_distinguished_name ]
CN = my-server.net # legacy

[ v3_req ]
subjectAltName = @alt_names

[alt_names]
DNS.1 = my-server.net
DNS.3 = www.my-server.net
IP.1  = 127.0.0.1

List ecdsa parameters

openssl ecparam -list_curves

secp112r1 : SECG/WTLS curve over a 112 bit prime field
secp112r2 : SECG curve over a 112 bit prime field
secp128r1 : SECG curve over a 128 bit prime field
secp128r2 : SECG curve over a 128 bit prime field
secp160k1 : SECG curve over a 160 bit prime field
secp160r1 : SECG curve over a 160 bit prime field
secp160r2 : SECG/WTLS curve over a 160 bit prime field
secp192k1 : SECG curve over a 192 bit prime field
secp224k1 : SECG curve over a 224 bit prime field
secp224r1 : NIST/SECG curve over a 224 bit prime field
secp256k1 : SECG curve over a 256 bit prime field
secp384r1 : NIST/SECG curve over a 384 bit prime field
secp521r1 : NIST/SECG curve over a 521 bit prime field
prime192v1: NIST/X9.62/SECG curve over a 192 bit prime field
prime192v2: X9.62 curve over a 192 bit prime field
prime192v3: X9.62 curve over a 192 bit prime field
prime239v1: X9.62 curve over a 239 bit prime field
prime239v2: X9.62 curve over a 239 bit prime field
prime239v3: X9.62 curve over a 239 bit prime field
prime256v1: X9.62/SECG curve over a 256 bit prime field
sect113r1 : SECG curve over a 113 bit binary field
sect113r2 : SECG curve over a 113 bit binary field
sect131r1 : SECG/WTLS curve over a 131 bit binary field
sect131r2 : SECG curve over a 131 bit binary field
sect163k1 : NIST/SECG/WTLS curve over a 163 bit binary field
sect163r1 : SECG curve over a 163 bit binary field
sect163r2 : NIST/SECG curve over a 163 bit binary field
sect193r1 : SECG curve over a 193 bit binary field
sect193r2 : SECG curve over a 193 bit binary field
sect233k1 : NIST/SECG/WTLS curve over a 233 bit binary field
sect233r1 : NIST/SECG/WTLS curve over a 233 bit binary field
sect239k1 : SECG curve over a 239 bit binary field
sect283k1 : NIST/SECG curve over a 283 bit binary field
sect283r1 : NIST/SECG curve over a 283 bit binary field
sect409k1 : NIST/SECG curve over a 409 bit binary field
sect409r1 : NIST/SECG curve over a 409 bit binary field
sect571k1 : NIST/SECG curve over a 571 bit binary field
sect571r1 : NIST/SECG curve over a 571 bit binary field
c2pnb163v1: X9.62 curve over a 163 bit binary field
c2pnb163v2: X9.62 curve over a 163 bit binary field
c2pnb163v3: X9.62 curve over a 163 bit binary field
c2pnb176v1: X9.62 curve over a 176 bit binary field
c2tnb191v1: X9.62 curve over a 191 bit binary field
c2tnb191v2: X9.62 curve over a 191 bit binary field
c2tnb191v3: X9.62 curve over a 191 bit binary field
c2pnb208w1: X9.62 curve over a 208 bit binary field
c2tnb239v1: X9.62 curve over a 239 bit binary field
c2tnb239v2: X9.62 curve over a 239 bit binary field
c2tnb239v3: X9.62 curve over a 239 bit binary field
c2pnb272w1: X9.62 curve over a 272 bit binary field
c2pnb304w1: X9.62 curve over a 304 bit binary field
c2tnb359v1: X9.62 curve over a 359 bit binary field
c2pnb368w1: X9.62 curve over a 368 bit binary field
c2tnb431r1: X9.62 curve over a 431 bit binary field
wap-wsg-idm-ecid-wtls1: WTLS curve over a 113 bit binary field
wap-wsg-idm-ecid-wtls3: NIST/SECG/WTLS curve over a 163 bit binary field
wap-wsg-idm-ecid-wtls4: SECG curve over a 113 bit binary field
wap-wsg-idm-ecid-wtls5: X9.62 curve over a 163 bit binary field
wap-wsg-idm-ecid-wtls6: SECG/WTLS curve over a 112 bit prime field
wap-wsg-idm-ecid-wtls7: SECG/WTLS curve over a 160 bit prime field
wap-wsg-idm-ecid-wtls8: WTLS curve over a 112 bit prime field
wap-wsg-idm-ecid-wtls9: WTLS curve over a 160 bit prime field
wap-wsg-idm-ecid-wtls10: NIST/SECG/WTLS curve over a 233 bit binary field
wap-wsg-idm-ecid-wtls11: NIST/SECG/WTLS curve over a 233 bit binary field
wap-wsg-idm-ecid-wtls12: WTLS curve over a 224 bit prime field
Oakley-EC2N-3: 
      IPSec/IKE/Oakley curve #3 over a 155 bit binary field.
      Not suitable for ECDSA.
      Questionable extension field!
Oakley-EC2N-4: 
      IPSec/IKE/Oakley curve #4 over a 185 bit binary field.
      Not suitable for ECDSA.
      Questionable extension field!
brainpoolP160r1: RFC 5639 curve over a 160 bit prime field
brainpoolP160t1: RFC 5639 curve over a 160 bit prime field
brainpoolP192r1: RFC 5639 curve over a 192 bit prime field
brainpoolP192t1: RFC 5639 curve over a 192 bit prime field
brainpoolP224r1: RFC 5639 curve over a 224 bit prime field
brainpoolP224t1: RFC 5639 curve over a 224 bit prime field
brainpoolP256r1: RFC 5639 curve over a 256 bit prime field
brainpoolP256t1: RFC 5639 curve over a 256 bit prime field
brainpoolP320r1: RFC 5639 curve over a 320 bit prime field
brainpoolP320t1: RFC 5639 curve over a 320 bit prime field
brainpoolP384r1: RFC 5639 curve over a 384 bit prime field
brainpoolP384t1: RFC 5639 curve over a 384 bit prime field
brainpoolP512r1: RFC 5639 curve over a 512 bit prime field
brainpoolP512t1: RFC 5639 curve over a 512 bit prime field
SM2       : SM2 curve over a 256 bit prime field

2.9. Making an CA

When looking at the following code, pay a lot of attention to the -x509 switch to the req command.

-x509

This option outputs a certificate instead of a certificate request. This is typically used to generate test certificates. It is
implied by the -CA option.

This option implies the -new flag if -in is not given.

If an existing request is specified with the -in option, it is converted to a certificate; otherwise a request is created from
scratch.

Unless specified using the -set_serial option, a large random number will be used for the serial number.

Unless the -copy_extensions option is used, X.509 extensions are not copied from any provided request input file.

X.509 extensions to be added can be specified in the configuration file, possibly using the -config and -extensions options, and/or
using the -addext option.

2.9.1. TODO RSA version

This section is unfinished and does not include client generation.

This section is config-file based, which is in theory better than just parameters, but I do not care for private use.

How to generate a root cert:

#!bash

printf 'Hello\n'

printf 'Deleting CA directory\n'

rm -rf "CA_directory"

mkdir -p CA_directory/root/{certs,newcerts,crl,private,csr}

echo 1000 > CA_directory/root/serial
echo 1000 > CA_directory/root/crlnumber
touch CA_directory/root/index.txt

cd CA_directory/root/

openssl req -config <(printf '%s' '
[ca]
default_ca = CA_default # Section redirection

[ CA_default ]
dir = ./CA_directory/root
certs = $dir/certs
crl_dir = $dir/crl
new_certs_dir = $dir/newcerts # how is it different from certs?
database = $dir/index.txt
private_keys = $dir/private/ca.key.pem
certificate = $dir/certs/ca.cert.pem
crlnumber = $dir/crlnumber
crl = $dir/crl/ca.crl.pem
crl_extensions = crl_ext
cefault_crl_days = 30

name_opt = ca_default # magic?
cert_opt = ca_default # magic?
default_days = 375 # how long standard certs signed _with_this_ca_ live
preserve = no # magic
policy = policy_strict # root CA gets its policy from a section called policy_strict
# I guess that for a simpleton certificate for a personal server none of this is needed?

[ policy_strict ] # which certs a CA root can sign
countryName = match
stateOrProvinceName = match
organizationName = match
organizationalUnitName = optional
commonName = supplied
emailAddress = optional

[ req ]
default_bits = 4096
distinguished_name = req_distinguished_name
string_mask = utf8only
default_md = sha256
x509_extensions = v3_ca
prompt = no

[ req_distinguished_name ] 
C = TS
ST = TestProvince
L = TestCity
O = TestCompany
OU = TestCompanyDepartment
CN = My CA Root Certificate

[ v3_ca ]# man openssl-x509v3_config
subjectKeyIdentifier = hash # unique code, identifying certs, hash means use a hash of the cert
authorityKeyIdentifier = keyid:always,issuer # add signing key info when signing certificates
basicConstraints = critical, CA:true, pathlen:1 # must be a CA cert, can only sign non-further-signatures certs
keyUsage = critical, digitalSignature, cRLSign, keyCertSign 

') -newkey rsa -keyout private/ca.key.pem -x509 -days 7300 \
        -extensions v3_ca -out certs/ca.cert.pem -nodes

2.9.2. A simpler RSA version

openssl req
        -x509\
        -newkey rsa -keyout ca.key.pem -out ca.cert.pem \
         -days 7300 \
         -nodes \
         -subj "/C=NL/ST=Zuid Holland/L=Rotterdam/O=ACME Corp/OU=IT Dept/CN=localhost"

# generate keypair
openssl req \
        -new \
        -newkey rsa -keyout client0.key -out client0.csr.pem \
        -subj "/C=NL/ST=Zuid Holland/L=Rotterdam/O=ACME Corp/OU=IT Dept/CN=localhost" \
        -nodes
# sign
openssl x509 -req \
        -extfile <(printf '%s' 'subjectAltName = DNS:localhost,DNS:blabla.org') \
        -CA ca.cert.pem -CAkey ca.key.pem -in client0.csr.pem -out client0.cert.pem -CAcreateserial

The important thing is that the SAN extension is added during signing, not generating a keypair.

2.9.3. CA using ECDSA

PARAM=$(openssl genpkey -genparam -algorithm ec \
     -pkeyopt ec_paramgen_curve:P-256)
printf '%s\n' "$PARAM"
 openssl req \
        -x509 \
        -newkey ec:<(printf '%s\n' "$PARAM") -keyout ca.key.pem -out ca.cert.pem \
         -days 7300 \
         -nodes \
         -subj "/C=NL/ST=Zuid Holland/L=Rotterdam/O=ACME Corp/OU=IT Dept/CN=localhost"

# generate keypair
openssl req \
        -new \
        -newkey ec:<(printf '%s' "$PARAM") -keyout client0.key -out client0.csr.pem \
        -subj "/C=NL/ST=Zuid Holland/L=Rotterdam/O=ACME Corp/OU=IT Dept/CN=localhost" \
        -nodes
# sign
openssl x509 -req \
        -extfile <(printf '%s' 'subjectAltName = DNS.1:localhost,DNS.2:blabla.org,IP.1:127.0.0.1') \
        -CA ca.cert.pem -CAkey ca.key.pem -in client0.csr.pem -CAcreateserial -out  client0.cert.pem
# check that it works
openssl x509 -text -noout -in client0.cert.pem