The Rails asset pipeline is really meant for structural / design images, such as backgrounds, icons, banners, etc..). Dynamic assets should go in the public directory [source below]
It's probably a good idea to serve static assets through Nginx or Apache or whatever your web-server is, or place them in the public directory of your Rails app.
That should solve your problem right there.. e.g. make a separate path for static assets into which you upload those images with rmagick / carrierwave, or whatever gem you prefer.
The asset pipeline only knows about images which are present during start-up. So separating static / uploaded assets into a separate directory , and serving it directly through the web-server, will help -- it should also be much faster.
you'll need something like this in your configuration:
# Disable Rails's static asset server (Apache or nginx will already do this)
config.serve_static_assets = false
# Compress JavaScripts and CSS
config.assets.compress = true
# Don't fallback to assets pipeline if a precompiled asset is missed
config.assets.compile = false
# Generate digests for assets URLs
config.assets.digest = true
# UNCOMMENT the header that your server uses for sending files
# config.action_dispatch.x_sendfile_header = "X-Sendfile" # for apache
# config.action_dispatch.x_sendfile_header = 'X-Accel-Redirect' # for nginx
More General:
http://railscasts.com/episodes/279-understanding-the-asset-pipeline
http://guides.rubyonrails.org/asset_pipeline.html
Rails 3.1: Should File Uploads be added to asset pipeline?
Regarding serving images outside asset pipeline:
http://mrjaba.posterous.com/rails-31-asset-pipeline-with-nginx-and-passen
http://trackingrails.com/posts/rails-31-and-asset-pipeline-problems-with-apache
http://pastebin.com/kC4Ba40U
https://github.com/defunkt/resque/issues/418