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I might be wrong but would the trick maybe be to break it down bit by bit, so for instance break off your existing file upload stuff and replace it with CarrierWave or something different. I don't know what your codebase is like but doing it that way should in theory make it more copable to slowly tick it up to rails 3+

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Yeah, that's likely the best way to do it. Problem is, our image uploads now number in the high hundreds of thousands (not counting thumbnails).

The other problem is, we are short-staffed. So, if I tackle this, it takes me off other projects for 2+ weeks.

It looks like there is a fairly active Rails 3 fork of attachment_fu (what we use): https://github.com/pothoven/attachment_fu

Gotcha, there's also some information on migrating to paperclip[1] which might suit and I'm sure someone will have done similar for CarrierWave. Of course none of that helps with being short staffed.

[1]https://gist.github.com/serek/375203

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