Issue #5137 has been updated by Chris White. I also just noticed that if I use `--enable-shared` with `./configure`, the library reference to the dylib disappears in the installed version, but remains in the source tree version: SOLAR:~ chriswhite$ otool -L ~/Source/Repository/ruby/ruby ; otool -L ~/Ruby/ruby-trunk/bin/ruby /Users/chriswhite/Source/Repository/ruby/ruby: /Users/chriswhite/Ruby/ruby-trunk/lib/libruby.1.9.1.dylib (compatibility version 1.9.1, current version 1.9.1) /usr/lib/libSystem.B.dylib (compatibility version 1.0.0, current version 125.2.11) /usr/lib/libobjc.A.dylib (compatibility version 1.0.0, current version 227.0.0) /Users/chriswhite/Ruby/ruby-trunk/bin/ruby: /usr/lib/libSystem.B.dylib (compatibility version 1.0.0, current version 125.2.11) /usr/lib/libobjc.A.dylib (compatibility version 1.0.0, current version 227.0.0) SOLAR:~ chriswhite$ ---------------------------------------- Bug #5137: Ruby SVN Revision 32800: Cannot run installed ruby interpreter, Malformed Mach-o file http://redmine.ruby-lang.org/issues/5137 Author: Chris White Status: Open Priority: Normal Assignee: Category: Target version: ruby -v: ruby 1.9.2p290 (2011-07-09) [x86_64-darwin10.8.0] I have compiled Ruby trunk, with the following configure options: ./configure --prefix=/Users/chriswhite/Ruby/ruby-trunk And after that: make clean && make && make install When I attempt to run the installed version, I get the following: SOLAR:ruby chriswhite$ ~/Ruby/ruby-trunk/bin/ruby -v -bash: /Users/chriswhite/Ruby/ruby-trunk/bin/ruby: Malformed Mach-o file However, when I run the version in the source tree I get: SOLAR:ruby chriswhite$ ./ruby -v ruby 1.9.4dev (2011-08-01 trunk 32800) [x86_64-darwin10.8.0] It seem that something in the `make install` process is causing this issue, but I'm not sure what it is. The ruby -v I've indicated is the version of ruby used when compiling trunk. This occurs for me on Mac OSX 10.6.8. Let me know any specific information you need and I'll provide it as soon as possible. -- http://redmine.ruby-lang.org