I’m reading a new chapter of The Imposter’s Handbook: Season 2 that Rob and I are working on. He’s digging into the internals of what’s exactly in your .

Decoding a certificate

I generated a key with no password:

ssh-keygen -t rsa -C [email protected]

Inside the generated file is this text, that we’ve all seen before but few have cracked open.

-----BEGIN RSA PRIVATE KEY-----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-----END RSA PRIVATE KEY-----

The private key is an ASN.1 (Abstract Syntax Notation One) encoded data structure. It’s a funky format but it’s basically a packed format with the ability for nested trees that can hold booleans, integers, etc.

However, ASN.1 is just the binary packed “payload.” It’s not the “container.” For example, there are envelopes and there are letters inside them. The envelope is the (Privacy Enhanced Mail) format. Such things start with —– BEGIN SOMETHING —– and end with —– END SOMETHING ——. If you’re familiar with , your spidey sense may tell you that this is a encoded file. Not everything that’s turns into a friendly ASCII string. This turns into a bunch of bytes you can view in .

We can first decode the PEM file into HEX. Yes, I know there’s lots of ways to do this stuff at the command line, but I like showing and teaching using some of the many encoding/ websites and utilities there are out there. I also love using https://cryptii.com/ for these things as you can build a visual pipeline.

308204A40201000282010100B5DF00B3CE6C3948E3923575DAE8
CC2199A1C9E81791C9866935A4DF5F6F401DFE7292215AED2606
47BC476F234729BD90B423D918DA3B501D4B1B0BCB8851D87CA7
63B97A0526C852B01A9BF682FDE57326683BAA35628CF2914E3E
DB746E5D60D65848488BF7CB7FF97571A097175CE118F3773959
C0A7CA816FE7C306E1319E1E2FF47285CAA5D1A502AB5052A6E9
DAC1BB582AD7206249741BD40C8403410D08B27E8C2B89CA040D
74B9C26657EA24EC310F9321A4D372A0031F9589E9FD10BBE8EC
FD0037BE4D9B55BD1623FA81FA0DBD45C3029285EDDBB51539F8
AF7A5E2F3CE3E74CB919C89F5987E84588BB38F87123870560E5
snip

This ASN.1 JavaScript decoder can take the HEX and parse it for you. Or you can that ASN.1 packed format at the *nix command line and see that there’s nine big integers inside (I trimmed them for this blog).

openssl asn1parse -in notreal
0:d=0 hl=4 l=1188 cons: SEQUENCE
4:d=1 hl=2 l= 1 prim: INTEGER :00
7:d=1 hl=4 l= 257 prim: INTEGER :B5DF00B3CE6C3948E3923575DAE8CC2199A1C9E81791C9866935A4DF5F6F401DFE7292215
268:d=1 hl=2 l= 3 prim: INTEGER :010001
273:d=1 hl=4 l= 257 prim: INTEGER :8195EB82324A9A667CFFE867991AD697FA4774FD920DA671C6F51A0CAE8B2E3C30D8A1967
534:d=1 hl=3 l= 129 prim: INTEGER :E22B40AC22007370E309E68A29C64EEF085B6937D8B808F74D2862EDEDCBC8CB18BEAAD48
666:d=1 hl=3 l= 129 prim: INTEGER :CDDC00D77FD6E9E7EE83AD95F1805076FAE3690D817C47ED4FA05B7872B5631C6174DEAA7
798:d=1 hl=3 l= 128 prim: INTEGER :747EECEFFD0F9866D43B3C497C5D0E3967679659D2C270B3D9456D37BADDD5CE6F2F7ED4B
929:d=1 hl=3 l= 128 prim: INTEGER :742961DC388A184144E8CEE9DE75AE72050E8FF80C0A0A38520745B648DC2BCA170030A97
1060:d=1 hl=3 l= 129 prim: INTEGER :997742BA4458617495BE121EFF68893C9BC0A1A38226E6F14E16B9FDF5EE072981790499E

Per the spec the format is this:

   An RSA private key shall have ASN.1 type RSAPrivateKey:

RSAPrivateKey ::= SEQUENCE {
version Version,
modulus INTEGER, -- n
publicExponent INTEGER, -- e
privateExponent INTEGER, -- d
1 INTEGER, -- p
prime2 INTEGER, -- q
exponent1 INTEGER, -- d mod (p-1)
exponent2 INTEGER, -- d mod (q-1)
coefficient INTEGER -- (inverse of q) mod p }

I found the description for how RSA works in this blog post very helpful as it uses small numbers as examples. The variable names here like p, q, and n are agreed upon and standard.

The fields of type RSAPrivateKey have the following meanings:
o version is the version number, for compatibility
with future revisions of this document. It shall
be 0 for this version of the document.
o modulus is the modulus n.
o publicExponent is the public exponent e.
o privateExponent is the private exponent d.
o prime1 is the prime factor p of n.
o prime2 is the prime factor q of n.
o exponent1 is d mod (p-1).
o exponent2 is d mod (q-1).
o coefficient is the Chinese Remainder Theorem
coefficient q-1 mod p.

Let’s look at that first number q, the prime factor p of n. It’s super long in Hexadecimal.

747EECEFFD0F9866D43B3C497C5D0E3967679659D2C270B3D945
6D37BADDD5CE6F2F7ED4BC600A002C2FC11A4A42EBAFA1B3D354
52D1B33CFCF1A3978B29D1E7F8C7DFEE8888487D73795AB6D6D3
80EC99C7F077CCF956FECA5853416D8B16CBD89648526E941A65
2E1AE72CF0511425BCF1E9E540B0CA23655ABEFADAAD028B

That hexadecimal number converted to is this long ass number. It’s 308 digits long!

22959099950256034890559187556292927784453557983859951626187028542267181746291385208056952622270636003785108992159340113537813968453561739504619062411001131648757071588488220532539782545200321908111599592636973146194058056564924259042296638315976224316360033845852318938823607436658351875086984433074463158236223344828240703648004620467488645622229309082546037826549150096614213390716798147672946512459617730148266423496997160777227482475009932013242738610000405747911162773880928277363924192388244705316312909258695267385559719781821111399096063487484121831441128099512811105145553708218511125708027791532622990325823

It’s hard work to prove this number is prime but there’s a great Integer Factorization Calculator that actually uses WebAssembly and your own local CPU to check such things. Expect to way a long time, sometimes until the sun death of the universe. 😉

Rob and I are finding it really cool to dig just below the surface of common things we look at all the time. I have often opened a key file in a text file but never drawn a straight and complete line through decoding, unpacking, decoding, all the way to a math mathematical formula. I feel I’m filling up some major gaps in my knowledge!


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