How to handle OpenSSL and not get hurt

Stuff you wished to know before you every needed to touch the OpenSSL library

This page is constructed as a personal braindump to be able to share some point of reference with those involved with OpenSSL. On the web OpenSSL is poorly documented and even the book Network Security with OpenSSL doesn't touch the advanced inner workings of the library. The library and its CLI tools are a part of our everyday Grid life and working with it, as intimately as developing callback functions and home-brew proxy certificate verification routines, has let me research how stuff works deeply from within the rabbit hole of the library itself.

I'd like to invite everybody who reads this to contribute tips, tricks, {code,wiki}-patches, need-to-knows, pitfalls, quirks, interesting routines, &c to this page directly or for external to Nikhef people through my email address.

You can contact me via email: okoeroo apestaartje nikhef punt nl.

Tip #1

When in true doubt: Use the source! When you're looking for anything particular or specialized and you really wish to know how OpenSSL is handling this: Use the Source!. There are more gems in the documentation of the OpenSSL source tarballs and it's easily grep-able.

Background information

This section will have all kinds of background information regarding OpenSSL, Proxy certificates, CAs, formatting details and other (hopefully) useful tidbits.

The general 'how do (proxy) certificates work' and 'what is a proxy certificate'

When (identity) delegation are used in a world full of X.509 certificates it means that you are using proxy certificates. Proxy certificates come in various shapes, forms and types. Some of the basics properties are consistent:

• It's an X.509 certificate
• Has a public and private key pair.
• The first delegated proxy certificate is signed by an End-Entity Certificate (EEC). An EEC means your personal certificate.
• Proxy certificates can signed and follow other proxy certificates

A certificate chain with one delegation, will be constructed like this:

1. CA certificate
2. EEC (personal, server or service certificate)
3. proxy certificate

In short, the construction steps (certificate "Genesis") to a proxy certificate:

• The CA operator creates a key pair and a signing request for the root CA certificate
• The CA operator (self-)signs its own request with its own private key
• A user creates a key pair, a signing request and send that off to a CA operator
• The CA operator performs identity vetting on the user and its signing request
• The CA operator creates the certificate from the signing request, signs it with the CA's private key and returns a brand new certificate to the user
• The user can use {grid,voms}-proxy-init to generate a new keypair, signing request for the proxy certificate and sign the proxy certificate with his/her private key.

Adding another proxy certificate layer is a repeat of the final step, but instead of using the user's certificate and private key, the certificate and private key of the latest created proxy certificate are used to create the next delegation and sign that proxy certificate.

A more complex certificate chain:

1. CA certificate
2. intermediate or sub-CA certificate
3. yet another intermediate or sub-CA certificate
4. EEC (personal, server or service certificate)
5. proxy certificate
6. another proxy certificate

What does that library call really do?

There exists X509_STORE_CTX_get_chain(X509_STORE_CTX *ctx) and X509_STORE_CTX_get1_chain(X509_STORE_CTX *ctx). The difference is that the X509_STORE_CTX_get_chain() will only return a reference to the certificate chain (type STACK_OF (X509) *) from within the X509_STORE_CTX structure and the X509_STORE_CTX_get1_chain() will make a duplicate certificate chain that will need to be free()'d.

Freeing a STACK_OF (X509) * is not to be done with just free(). That will create a memory leak. Also a X509_free (X509) * and using a STACK_OF (X509) * as input will create a memory leak. The proper way to free a STACK_OF (X509) * is to use sk_X509_pop_free(st, free_func), where for free_func you should use X509_free. Example: sk_X509_pop_free(chain, X509_free). Warning: do not get confused with sk_X509_free() which will accept the STACK_OF (<type>) *, but does not pop the stack to free all the individual certificates of the chain (which will be equal to an instant memory leakage for any certificate chain longer then one certificate).

To get the issuer DN and subject DN you can use constructions like:

char * cert_DN   = X509_NAME_oneline (X509_get_subject_name (cert), NULL, 0);
char * issuer_DN = X509_NAME_oneline (X509_get_issuer_name (cert), NULL, 0);

or

char cert_DN[255];
char issuer_DN[255];
X509_NAME_oneline (X509_get_subject_name (cert), cert_DN, 255);
X509_NAME_oneline (X509_get_issuer_name (cert), issuer_DN, 255);

In the first construction you'll need to free both the cert_DN and the issuer_DN. In the second example a static buffer is used and filled by the X509_NAME_oneline() routines.

Interesting OpenSSL CLI need-to-knows

s_client foo

example: openssl s_client -connect 127.0.0.1:13050 -msg -nbio -ssl3 -CApath ~/dvl/ca/ -cert ~/dvl/ca/newcert.pem -key ~/dvl/ca/newkey.pem

-CAfile vs. -CApath

Using the -CAfile <specific CA file> will send this certificate over the wire to the server-side. This will typically fail the verification of the certificate chain at the server-side, because it is not allowed to transfer the self-signed certificates. The trust-anchors should be installed at the service, not transfered by the client (for obvious reasons). The -CAfile <file> will also be used for the verification of the server-side certificate, but it's safer to use the -CApath <path to one or more CA certificates> option.

How to calculate the hash value used by CA file names

OpenSSL CLI and the OpenSSL library functions will search in a default path and/or a given path to the needed (installed) CA files when it needs to verify a certificate chain. By convention a client (and server) will never provide the (final) CA certificate to the connected peer. The trust in the peer certificate (chain) has to be completed by adding the CA certificate(s) to the chain for it to verify completely.

This means that the OpenSSL CLI tool and/or library functions need to search one or more (stated) paths for the use CA files by the peers. OpenSSL will search in the -CApath directory by the hash of the used CA.

Run the following command:

openssl x509 -hash -noout -in cacert.pem
0e52ca4f

Copy or rename the cacert.pem file to 0e52ca4f.0. The .0 indicates that it is the root CA. A .1 extension indicates a subordinate CA. The .1 doesn't always work because of differences in the OpenSSL implementations between its versions. Also Java libraries will handle the .1 each in a different way.

Using proxy certificates and s_client

Setting up a mutually authenticated SSL connection means that you'll receive the server-side certificate for your (automated) verification and that your (client-side) credentials are to be passed over to the server-side for authentication (in that order).

To perform a proper verification of the certificate chain, the server-side must be capable of constructing the complete certificate chain and through a challenge-response mechanism the private key used must fit the final certificate. When using a complex certificate chain where only the CA certificates are distributed to the service nodes a client must send its EEC and proxy certificates to the server-side.

To send the EEC and the proxy to the server-side with OpenSSL s_client you can use -CAfile to fill the gap in the certificate chain:

openssl s_client -connect 127.0.0.1:13050 \
     -debug -state -nbio \
     -CApath /etc/grid-security/certificates/ 
     -CAfile $HOME/.globus/usercert.pem \
     -cert /tmp/x509up_u501 \
     -key /tmp/x509up_u501

The -cert is used for the proxy certificate, -key for the private key (which is in the same file as the proxy certificate), the -CAfile is used for your EEC (your personal certificate) and the -CApath refers to the directory filled with root CA certificates. The -debug, -state and -nbio are not relevant here.

Downloading the host, service or user certificate from an OpenSSL session

Copy and execute the following little script. Rename the SERVER and PORT variable and you will end up with the certificate of the service in PEM format on file.

#!/bin/sh
OPENSSL=openssl
SED=sed
CAT=cat
TIMEOUT=1
SERVER=kuiken.nikhef.nl
PORT=8443
CERTDIR=/etc/grid-security/certificates/
PROXY_FILE=/tmp/x509up_u501
TMP_FILE=/tmp/cert_fetch.tmp
OUTPUTFILE=certificate_${SERVER}_${PORT}.pem
$OPENSSL s_client -connect ${SERVER}:${PORT} -CApath ${CERTDIR}  -key ${PROXY_FILE} -CAfile ${PROXY_FILE} -cert ${PROXY_FILE} -showcerts > ${TMP_FILE} &
PID=$!
sleep $TIMEOUT
kill -TERM $PID 2>/dev/null
$CAT $TMP_FILE | $SED -ne '/-----BEGIN CERTIFICATE-----/,/-----END CERTIFICATE-----/p' > $OUTPUTFILE
echo The host certificate is written in: $OUTPUTFILE
exit 0