Ruby and Rails issues on Snow Leopard Upgrade

I had been holding off upgrading my MacBook to Snow Leopard as I figured there would be issues with the Ruby installation and some of the gems. I decided to go for it yesterday... yup, there were issues...

Snow Leopard comes with Ruby 1.8.7 already installed so it is tempting to use that but I follow Dan Benjamin's advice and install my own versions of MySQL, Ruby and Ruby gems in /usr/local. Dan has produced a series of excellent guides on installing Rails, etc on the Mac. HERE and HERE for example. However, his instructions do not always work for me. Here are the steps I needed to do get my setup running on my upgraded laptop.

The main issue is that you want Ruby and MySQL compiled as 64 bit applications. If you have Ruby as 32 bit and MySQL as 64 then things will break with cryptic messages.

I don't like MacPorts and, although I like installing binary packages, I prefer to compile Ruby etc. That way I retain full control on installing new versions.

MySQL:
1. Follow Dan Benjamin's advice on XCode, paths, etc
2. Dump your existing MySQL contents.
3. Download and compile MySQL as per Dan's instructions.
4. Load your data and check that MySQL is working as expected.

Ruby:
1. Don't compile the code as root/sudo - use sudo to run make install and gem install, but nothing else.
2. Make a list of your currently installed gems (gem list --local > gem.list)
3. Download and compile readline-6.0 (http://ftp.gnu.org/gnu/readline/). Supposedly you no longer need to do this, but I found it necessary.
4. Download Ruby into a user writeable directory in /usr/local/src or ~/src
5. Move the existing /usr/local/bin/ruby and /usr/local/lib/ruby (if you have them) - you shouldn't need to but it will make it easier to validate that the new version has been installed
6. Run ./configure with these options
./configure --enable-shared --enable-pthread CFLAGS=-D_XOPEN_SOURCE=1 --with-readline-dir=/usr/local
7. Follow with make, sudo make install
8. Check that you now have /usr/local/bin/ruby and check that it is compiled as as 64 bit by running 'file /usr/local/bin/ruby'. You should see '/usr/local/bin/ruby: Mach-O 64-bit executable x86_64'.
9. Now download and install rubygems as per Dan Benjamin.
10. Any gems that have C extensions need to be recompiled, but to be safe you should install all of them (You could copy them from your old installation but don't). I have a script for doing this which I should post.
11. The MySQL gem is different - you want to pass the path of the mysql dir to the gem install, like this:
sudo gem install mysql -- --with-mysql-dir=/usr/local/mysql
Note that you should not need to specify ARCH_FLAGS or anything else, which is recommended elsewhere - not needed.
12. Install Phusion Passenger if you are using that.
13. Check out your Rails apps. Use 'script/console' and try some simple finds on your models.

If you see this: NameError (uninitialized constant MysqlCompat::MysqlRes) it is most likely that your Ruby and/or gems are not compiled as 64 bit. You will see all sorts of posts where people have seen that error. I think most of them are the result of this mismatch.

To check any executable/library just do 'file ' and see if it says 32-bit or 64-bit.