I\'ve got a rather large, 2.3 upgraded to Rails 3 application, that\'s fat enough it\'s not making it through the 60 second startup door at Heroku, and therefore it\'s crash
The heroku-forward gem will help you beat the 60s Heroku timeout.
This was due, at least in my case, to two things: 1) a lot of gems, and 2) Mongo taking a long time to initialize (big burdened database).
To fix the gems, on my local dev, I patched bundler Kernel#require statement so I could see which were taking the longest to load. Then, I tried to remove them. Barring that, I set them to :require => false and manually required them where they were needed.
Secondly, I monkey patched Mongoid so that it doesn't try to connect to the database when the app is starting. This helped dramatically with the slow boot time (removed over 10 seconds).
Heroku's boot timeout bit me too. I read several blog posts about how to get around it and ended up automating some of the solutions into a gem.
To reduce the startup time on deploy, you can trim the gems loaded at boot time (this doesn't mean you have to trim them from the app, just boot time).
gem_bench evaluates which gems are likely to not be needed at boot time.
I have an app with about 250 gems and was able to add :require => false to about 60 of them, with dramatic effects.
https://github.com/acquaintable/gem_bench
Disclaimer: I am the author of this open source ruby gem. I wrote the gem to aid myself in solving this exact problem: the 60 second timeout on Heroku.