Installing psycopg2 fails on MacOS with unclear error message

I had this problem running pip install psycopg2 while I was running OSX 10.14.4. I fixed it by:

1. Running pg_config and noticed the variable:

   CPPFLAGS = -I/usr/local/Cellar/icu4c/63.1/include -isysroot /Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.14.sdk -I/usr/local/opt/openssl/include -I/usr/local/opt/readline/include -I/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.14.sdk/usr/include/libxml2
   

   However /Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.14.sdk did not exist on my machine.

   So I changed it to /Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX.sdk

2. I ran these two commands:

   export CPPFLAGS="-I/usr/local/Cellar/icu4c/63.1/include -isysroot /Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.sdk -I/usr/local/opt/openssl/include -I/usr/local/opt/readline/include -I/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX10.14.sdk/usr/include/libxml2"
   
   pip install psycopg2
   

Thanks for adding the error log, without which it would have been very hard to find the issue. Nice work.

This part of the log was really interesting:

    gcc -Wno-unused-result -Wsign-compare -Wunreachable-code -fno-common -dynamic -DNDEBUG -g -fwrapv -O3 -Wall -arch x86_64 -g -DPSYCOPG_VERSION=2.8.2 (dt dec pq3 ext lo64) -DPG_VERSION_NUM=110002 -DHAVE_LO64=1 -I/Library/Frameworks/Python.framework/Versions/3.7/include/python3.7m -I. -I/usr/local/Cellar/postgresql/11.2_1/include -I/usr/local/Cellar/postgresql/11.2_1/include/server -c psycopg/typecast.c -o build/temp.macosx-10.9-x86_64-3.7/psycopg/typecast.o
    gcc -bundle -undefined dynamic_lookup -arch x86_64 -g build/temp.macosx-10.9-x86_64-3.7/psycopg/psycopgmodule.o build/temp.macosx-10.9-x86_64-3.7/psycopg/green.o build/temp.macosx-10.9-x86_64-3.7/psycopg/pqpath.o build/temp.macosx-10.9-x86_64-3.7/psycopg/utils.o build/temp.macosx-10.9-x86_64-3.7/psycopg/bytes_format.o build/temp.macosx-10.9-x86_64-3.7/psycopg/libpq_support.o build/temp.macosx-10.9-x86_64-3.7/psycopg/win32_support.o build/temp.macosx-10.9-x86_64-3.7/psycopg/solaris_support.o build/temp.macosx-10.9-x86_64-3.7/psycopg/connection_int.o build/temp.macosx-10.9-x86_64-3.7/psycopg/connection_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/cursor_int.o build/temp.macosx-10.9-x86_64-3.7/psycopg/cursor_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/column_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/replication_connection_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/replication_cursor_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/replication_message_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/diagnostics_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/error_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/conninfo_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/lobject_int.o build/temp.macosx-10.9-x86_64-3.7/psycopg/lobject_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/notify_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/xid_type.o build/temp.macosx-10.9-x86_64-3.7/psycopg/adapter_asis.o build/temp.macosx-10.9-x86_64-3.7/psycopg/adapter_binary.o build/temp.macosx-10.9-x86_64-3.7/psycopg/adapter_datetime.o build/temp.macosx-10.9-x86_64-3.7/psycopg/adapter_list.o build/temp.macosx-10.9-x86_64-3.7/psycopg/adapter_pboolean.o build/temp.macosx-10.9-x86_64-3.7/psycopg/adapter_pdecimal.o build/temp.macosx-10.9-x86_64-3.7/psycopg/adapter_pint.o build/temp.macosx-10.9-x86_64-3.7/psycopg/adapter_pfloat.o build/temp.macosx-10.9-x86_64-3.7/psycopg/adapter_qstring.o build/temp.macosx-10.9-x86_64-3.7/psycopg/microprotocols.o build/temp.macosx-10.9-x86_64-3.7/psycopg/microprotocols_proto.o build/temp.macosx-10.9-x86_64-3.7/psycopg/typecast.o -L/usr/local/lib -lpq -lssl -lcrypto -o build/lib.macosx-10.9-x86_64-3.7/psycopg2/_psycopg.cpython-37m-darwin.so
    ld: library not found for -lssl

The 2nd gcc had a mention of this:

-L/usr/local/lib -lpq -lssl -lcrypto -o ...

That means, compilation process was looking for a library (-l) that happens to be ssl. See gcc manual (https://linux.die.net/man/1/gcc). It says that -l is to search the library named library (in our case ssl) when linking.

Something with ssl library was missing.

Google search lead to a reported issue: https://github.com/psycopg/psycopg2/issues/492. Joe Kemp's answer (https://github.com/psycopg/psycopg2/issues/492#issuecomment-278481164) suggests setting an environment variable like so:

export LDFLAGS="-L/usr/local/opt/openssl/lib"

Other options were listed here: Can't install psycopg2 with pip in virtualenv on Mac OS X 10.7.

It appears that your setting LDFLAGS solved the issue.