Signed PDF verification in Origami with an Adobe PKCS#7 certificate - ruby

Summarized and clarified:
Using origami, extracting a certificate from a signed pdf (signed within e.g. Adobe Reader) I cannot verify the signature:
origami = Origami::PDF.read(File.open('/path/to/file.pdf', 'r'))
pdf_signature = origami.signature[:Contents]
cert = OpenSSL::PKCS7.new(pdf_signature).certificates.first
origami.verify(trusted_certs: [cert]) #=> false
As far as I can tell, this should always be true. So maybe Adobe uses a different byte range that it takes a SHA of when signing the PDF? How do I get that verify to work?
If it's any help, after tiptoing through the changes on origami master, I was able to get the exact OpenSSL error from the storecontext: V_ERR_UNABLE_TO_GET_ISSUER_CERT_LOCALLY - I presume it means from the X509::Store it sets up.
Full background
I'm trying to verify the digital signature of a PDF. Here's what I've got:
A PDF that I've signed using Adobe Acrobat (tried both Pro 10 and Reader DC)
The key was generated in Acrobat Pro, I have access to the .p12, or exporting as FDF, PKCS#7 or just "Certificate File". Have also tried loading this "Certificate File" via Apple's "Keychain Access" and exporting that as a .pem This gives the same result as OpenSSL::PKCS7.new(File.read('/path/to/exported.p7c')).certificates.first.to_pem which gives the same result as:
openssl pkcs7 -print_certs -inform der -in pkcs7file.p7c -out certificate.cer
So, I'm pretty sure I've extracted the certificate correctly.
Also, I can verify that exact same certificate is embedded in the PDF -
pdf_signature = origami.signature[:Contents]
OpenSSL::PKCS7.new(pdf_signature).certificates.first.to_pem #=> Same as above
With the Origami gem, I've tried loading the certificate and attempting verification:
cert = OpenSSL::X509::Certificate.new(File.read('/path/to/pem.cer'))
Origami::PDF.read(File.open('/path/to/file.pdf', 'r')).verify(trusted_certs: [cert])
Origami's output confirms the document has been signed, but the verify(..) method returns false.
Note that working through the code from this excellent answer works fine, but it only seems to work if you generate the X.509 keypair using openssl (e.g. the ruby-land bindings as per that code). Unfortunately I'm required to use the pre-existing Adobe-blessed signatures from the user's machines.
That said, aside from this I have very few restraints; I can ask the users to export their certificate in any other way that is useful to us (I can even run some simple code on their machines if necessary), though I mustn't transmit the private key in the procedure. I don't have to use Origami for the verification, but it does have to be a command accessible from ruby on an ubuntu server. The users are all running on Macs with reasonably up-to-date software.

I've gotten a little further from my original issue, but not by much:
Certificates require the correct extensions
In the original code from Harry Fairbanks' very useful answer, the extensions are paramount:
extension_factory = OpenSSL::X509::ExtensionFactory.new
extension_factory.issuer_certificate = cert
extension_factory.subject_certificate = cert
cert.add_extension extension_factory.create_extension('basicConstraints', 'CA:TRUE', true)
cert.add_extension extension_factory.create_extension('keyUsage', 'digitalSignature,keyCertSign')
cert.add_extension extension_factory.create_extension('subjectKeyIdentifier', 'hash')
So... following the rest of that answer, if you save the certificate to a pemfile, the extensions do not also get saved.
I was able to create a PDF, sign it with Origami using the key I exported from Acrobat reader, and then do the following:
cert = OpenSSL::PKCS7.new(pdf_signature).certificates.first
origami.verify(trusted_certs: [cert]) #=> false
## ... then run the extension factory snippet above
origami.verify(trusted_certs: [cert]) #=> true
Success! In fact, even Adobe Acrobat Reader was happy - which I couldn't get it to do with the self-signed certificate that Origami generated.
... however, when I sign the document using Adobe Acrobat Reader, with the same key, perform the same magical incantation on the cert, I still get false from the verify call.
Note: I have been told that this actually works for some people. Not sure why it failed for me - when I have a chance to play, will give it another go. Will mark this as answered for now!

It's possible the ciphers are different. It could be that the Adobe cipher is not the same one that the openssl is using and would then fail the verification check. Take a look at this. Details on ciphers
This might be useful too openssl commands

Related

Store and retreive RSA private key in Windows

I have a pretty simple scenario/requirement:
Generate RSA private/public key pair through OpenSSL or any online RSA key pair generator
Save the private key to the windows internal store (so it does not lay around as just a file somewhere
Create a PowerShell script, that looks into the store, locates the key, and uses it.
(basically, I will have a PS script, to which I send a 3rd party tool already encrypted password, and I expect that PS script to decrypt that password using a locally stored private key and use it on-the-fly)
This so far showed an unreachable goal, because:
I haven't found a way, how to import .pem file with the key
.cer file apparently does not contain the key
the only way (so far what I have found) how to import the key is conversion to .pfx file, which can be imported, BUT
.pfx file cannot be read as plain text - there seems to be no reasonable way from Powershell to locate the key and read it for usage in decryption
there is a module PSPKI, but it seems to accept the file and not the stored/installed certificate/key.
So anyone has any idea, how can I import a simple private key to Windows for later read-out from PowerShell for further usage?
Thank you!
Have a look at this class to load the PFX: https://learn.microsoft.com/en-us/dotnet/api/system.security.cryptography.x509certificates.x509certificate2?view=net-7.0
$cert = New-Object System.Security.Cryptography.X509Certificates.X509Certificate2("c:\my.pfx", "password");
Next step is to open the store. After you checked which one fits best (machine or user) you can use X509Store to read and write there. Do not forget the Open method. When a certificate with private key (off) is added the key ist stored and the file can be deleted.

OpenSSL public key for Firefox extension signing

I'm trying to bring back an old extension I made for Firefox 1.5 written in JavaScript. One of the changes introduced in Firefox 3.0 was the need for extension updates secured via either HTTPS or PKI. Since I can't use an SSL solution on my website, I need to use the PKI solution.
So, first up is generating the private and public keys. I was able to create CA and client (code signing) certificates using OpenSSL by following this guide. So, how I have two key and certificate pairs: ca.crt, ca.key, code.crt and code.key.
Now, I have to put the public key into the install.rdf's <em:updateKey> field. I did this with the command openssl -in code.key -outform DER -pubout and copied the resulting output (sans the ^-----.* lines) into my install.rdf. Now, the public key generated in this way is base64-encoded and ends with a couple equals signs. I haven't seen any examples that actually have these trailing characters. Is that OK, or did I pass the wrong options to OpenSSL?
Aside from this, using uhura to sign my update.rdf seems fairly straight-forward, but again there are no trailing =='s, which seems odd from the output I got via the OpenSSL command above.
Any help would be greatly appreciated!
I was able to get this working using a localhost webserver configuration. The OpenSSL command is the correct one to use in this case and the trailing padding is a coincidence, but it works when fetching updates.

Change ASN.1 tag type in CSR generated by Windows 2012 Active Directory Certificate Services

I'm trying, using OpenSSL 1.0.1e on Debian, to sign a Certificate Signing Request coming from a initial setup of a subordinate CA under Windows 2012 Active Directory Certificate Services (ADCS). My problem is that ADCS encode string items of the CSR using "PRINTABLESTRING" format.
I want to change the format used by ADCS from "PRINTABLESTRING" to "UTF8STRING" because OpenSSL do not recognize the equality of the string items and then reject the CSR (I use a match policy settings for attributes comparison).
I cannot find any option the change the format. Is this change is it possible ?
I have found interesting information about this point:
Open the original CSR and copy the base64 data between the "-----BEGIN CERTIFICATE REQUEST-----" and "-----END CERTIFICATE REQUEST-----" markers.
Put this data into a base64 decoder and save the output as a binary file. There are a variety of online services that can do this or if you prefer there are local tools as well.
Download/install a hex editor. Use it to open the decoded binary file.
Look for two values right before the countryName: 0C 02
Edit the value 0C (UTF8String) and change it to 13 (Printablestring)
Save the changes and use a base64 encoder to encode it back to base64.
Add the base64 data back in between the "-----BEGIN CERTIFICATE REQUEST-----" and "-----END CERTIFICATE REQUEST-----" markers.

Getting a web server certificate in ruby

I'm trying to write some ruby code to grab the Common Name (CN) value from a web server's SSL certificate but there doesn't seem to be any simple way to do this in ruby.
Well, I would beg to differ. It's documented well enough but not too many examples are available, which makes it a bit, but not too complicated :)
require 'openssl'
raw_cert = File.read (path_to_your_cert) # if your cert is in PEM or DER format
OR
raw_cert = OpenSSL::PKCS12.new(File.read(path_to_your_cert), your_pwd) # If you want to read a .p12 cert
cert = OpenSSL::X509::Certificate.new(raw_cert)
cert.subject
=> **************/CN=<Your Common Name>/***************
So you can parse cert.subject to find out the common name you need.
You can read more in-depth on SSL certs at http://ruby-doc.org/stdlib-2.0/libdoc/openssl/rdoc/OpenSSL/X509/Certificate.html

How to validate a signed DLL has been signed by me?

I have created a self generated certificate to sign a DLL. When I load this DLL into my C++ application I am able to validate if the code signing certificate is valid or not by using the WinVerifyTrust api.
But I am not able to find a way to detect that the DLL has been signed by one of my certificates. Even by using the CryptQueryObject api I do not find any useful information.
Does anyone have a idea on how to do this? Or is it event possible?
Thank you
CryptVerifyCertificateSignature isn't what you want?
If you sign a certificate using your private key, it can only be verified with your public key. That's how public-key cryptography works. If you can use a public key to verify the signature, then you know that the corresponding private key must have been used to sign it.
In case you need a version that also works on earlier versions of Windows than the one Bill Zeller showed you, you can use the following:
Use CryptQueryObject with CERT_QUERY_OBJECT_FILE
Use CryptMsgGetParam with CMSG_SIGNER_CERT_INFO_PARAM on the HCRYPTMSG you received from the previous call
Now use CertCompareIntegerBlob to compare your known (certificate) serial number (or numbers, in a loop) against the one in the file
If any of the known serial numbers matches, you're done. If all comparisons fail, it's not your cert.
Note: when looking at the serial number of the certificate in the file properties dialog, the bytes shown there appear in the reverse order when compared with the contents of the PCERT_INFO (CERT_INFO::SerialNumber) you get from the CryptMsgGetParam. So make sure that you store your own serial numbers reversed or reverse them before comparison.
Also note: you'll still need to have the certificate installed as trusted, in order for WinVerifyTrust (not mentioned above) to consider the code signature trusted at all. I just described the part about how to find out it's your own certificate that was used.

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