I'm having the same issue. I've followed all of the steps in Appendix E and
in the this post but still get the error message. I've also confirmed that
the fips lib is installed at: /usr/local/ssl/Release-iphoneos 

Here's my command line to configure the openssl build
./config no-asm no-krb5 no-gost
--with-fipslibdir=/usr/local/ssl/Release-iphoneos/lib
--openssldir=/usr/local/ssl/Release-iphoneos fips


Here's the log

Configured for darwin-i386-cc.
+ ASM_DEF=-UOPENSSL_BN_ASM_PART_WORDS
+ make 'CFLAG=-D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS -arch x86_64
-isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses' 'SHARED_LDFLAGS=-arch x86_64
-dynamiclib'
making all in crypto...
( echo "#ifndef MK1MF_BUILD"; \
    echo '  /* auto-generated by crypto/Makefile for crypto/cversion.c */';
\
    echo '  #define CFLAGS "cc -D_DARWIN_C_SOURCE
-UOPENSSL_BN_ASM_PART_WORDS -arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses"'; \
    echo '  #define PLATFORM "darwin-i386-cc"'; \
    echo "  #define DATE \"`LC_ALL=C LC_TIME=C date`\""; \
    echo '#endif' ) >buildinf.h
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o cryptlib.o cryptlib.c
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o mem.o mem.c
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o mem_dbg.o mem_dbg.c
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o cversion.o cversion.c
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o ex_data.o ex_data.c
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o cpt_err.o cpt_err.c
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o ebcdic.o ebcdic.c
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o uid.o uid.c
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o o_time.o o_time.c
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o o_str.o o_str.c
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o o_dir.o o_dir.c
cc -I. -I.. -I../include  -D_DARWIN_C_SOURCE -UOPENSSL_BN_ASM_PART_WORDS
-arch x86_64 -isysroot
/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.9.sdk
-Wno-unused-value -Wno-parentheses   -c -o o_fips.o o_fips.c
o_fips.c:60:10: fatal error: 'openssl/fips.h' file not found
#include <openssl/fips.h>


It doesn't look like any include path is getting set. Any help would be
greatly appreciated.
         ^



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