Building ruby 2.5.1 fails with openssl 1.0.2o_1

[papilip]

Hello all, i can not compile ruby 2.5.1 and ruby 2.6.0-preview1 with the same error.

macOS High Sierra Version 10.13.4 with homebrew. I use ruby-install with this command ruby-install ruby 2.5.1

compiling openssl_missing.c
In file included from openssl_missing.c:21:
./openssl_missing.h:75:11: warning: 'X509_STORE_get_ex_new_index' macro redefined [-Wmacro-redefined]
#  define X509_STORE_get_ex_new_index(l, p, newf, dupf, freef) \
          ^
/usr/local/Cellar/openssl@1.1/1.1.0h/include/openssl/x509_vfy.h:320:9: note: previous definition is here
#define X509_STORE_get_ex_new_index(l, p, newf, dupf, freef) \
        ^
openssl_missing.c:65:36: error: invalid application of 'sizeof' to an incomplete type 'HMAC_CTX'
      (aka 'struct hmac_ctx_st')
    HMAC_CTX *ctx = OPENSSL_malloc(sizeof(HMAC_CTX));
                                   ^     ~~~~~~~~~~
/usr/local/Cellar/openssl@1.1/1.1.0h/include/openssl/crypto.h:126:23: note: expanded from macro 'OPENSSL_malloc'
        CRYPTO_malloc(num, OPENSSL_FILE, OPENSSL_LINE)
                      ^~~
/usr/local/Cellar/openssl@1.1/1.1.0h/include/openssl/ossl_typ.h:102:16: note: forward declaration of
      'struct hmac_ctx_st'
typedef struct hmac_ctx_st HMAC_CTX;
               ^
openssl_missing.c:68:5: warning: implicit declaration of function 'HMAC_CTX_init' is invalid in C99
      [-Wimplicit-function-declaration]
    HMAC_CTX_init(ctx);
    ^
openssl_missing.c:78:2: warning: implicit declaration of function 'HMAC_CTX_cleanup' is invalid in C99
      [-Wimplicit-function-declaration]
        HMAC_CTX_cleanup(ctx);
        ^
openssl_missing.c:90:13: error: incomplete definition of type 'struct X509_crl_st'
        *psig = crl->signature;
                ~~~^
/usr/local/Cellar/openssl@1.1/1.1.0h/include/openssl/ossl_typ.h:121:16: note: forward declaration of
      'struct X509_crl_st'
typedef struct X509_crl_st X509_CRL;
               ^
openssl_missing.c:92:13: error: incomplete definition of type 'struct X509_crl_st'
        *palg = crl->sig_alg;
                ~~~^
/usr/local/Cellar/openssl@1.1/1.1.0h/include/openssl/ossl_typ.h:121:16: note: forward declaration of
      'struct X509_crl_st'
typedef struct X509_crl_st X509_CRL;
               ^
openssl_missing.c:102:13: error: incomplete definition of type 'struct X509_req_st'
        *psig = req->signature;
                ~~~^
/usr/local/Cellar/openssl@1.1/1.1.0h/include/openssl/x509.h:91:16: note: forward declaration of 'struct X509_req_st'
typedef struct X509_req_st X509_REQ;
               ^
openssl_missing.c:104:13: error: incomplete definition of type 'struct X509_req_st'
        *palg = req->sig_alg;
                ~~~^
/usr/local/Cellar/openssl@1.1/1.1.0h/include/openssl/x509.h:91:16: note: forward declaration of 'struct X509_req_st'
typedef struct X509_req_st X509_REQ;
               ^
3 warnings and 5 errors generated.
make[2]: *** [openssl_missing.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2
!!! Compiling ruby 2.5.1 failed!

If you can help me, many thanks !

[awolfson]

I had this exact same error, and I solved it by following these two recommendations:

1. Reinstall XCode Command Line Tools
2. Install without headers in /usr/local/include

I was on Mojave and installing Ruby version 2.5.3.

[rhenium]

I believe you fixed this already.

./openssl_missing.h:75:11: warning: 'X509_STORE_get_ex_new_index' macro redefined [-Wmacro-redefined]
#  define X509_STORE_get_ex_new_index(l, p, newf, dupf, freef) \

This error is due to multiple versions of OpenSSL being installed on the system. Removing the other or explicitly specifying the path where the desired OpenSSL version is installed to, by --with-openssl-dir=, should have resolved it.