Openssl key generation on OS X failing

Question

I am attempting to run our unit tests on a new clean mac for a Spring project. One test requires the generation of ssl keys.

I have installed openssl via homebrew but the error continues to persist.

Please see error below:

Using configuration from /Users/myuser/workspace/project/webapp/target/test-data/clientvpn/acc1/openssl.conf
default is an unsupported message digest type
13499:error:02001002:system library:fopen:No such file or directory:/BuildRoot/Library/Caches/com.apple.xbs/Sources/OpenSSL098/OpenSSL098-59/src/crypto/bio/bss_file.c:126:fopen('./index.txt.attr','rb')
13499:error:2006D080:BIO routines:BIO_new_file:no such file:/BuildRoot/Library/Caches/com.apple.xbs/Sources/OpenSSL098/OpenSSL098-59/src/crypto/bio/bss_file.c:129:
13499:error:0E078072:configuration file routines:DEF_LOAD:no such file:/BuildRoot/Library/Caches/com.apple.xbs/Sources/OpenSSL098/OpenSSL098-59/src/crypto/conf/conf_def.c:197:

Solution

I have solved the issue with many google searches and consultation with a colleague who has also recently moved to a mac.

The symlinks for the new openssl where not created when homebrew did the installation. If you run brew link openssl you will receive the following message Warning: openssl is keg-only and must be linked with --force

This leads the the solution. Homebrew needs to be explicitly told to create the correct links.

brew link --force openssl

If you now check which openssl you will notice it points to the brew installed version /usr/local/bin/openssl

Comments

[jww]

Type which openssl and report back.

[robinjohnobrien]

Thanks for the response. which openssl printed /usr/bin/openssl which is the for the non-homebrew version of openssl. Forcing brew to link the new openssl solved the problem. Please see answer below for a slightly longer description.

[IgorGanapolsky]

openssl:Error: '-CAcreateserial' is an invalid command.