We encountered this problem too and decided to dig deeper to fix it.
You are right about Rails class caching. The Style initializer removes
the :format, :geometry and :processors options from the options hash
and stores them as an instance variable. When Rails class caching is
on, every Style initialized after the first one will not have
the :format, :geometry and :processors options passed in, because they
were deleted from the class.

We've created an issue on Paperclip's Github:
http://github.com/thoughtbot/paperclip/issues/issue/277
We forked the repository and made the fix here:
git://github.com/pivotal-creationmix/paperclip.git

On Aug 12, 5:12 pm, Fernando Perez <li...@ruby-forum.com> wrote:
> > thumbnail etc. In that scenario the format stays the same, so if you use
> > a jpg you'll have a thumbnail jpg as well.
>
> Still what's strange is that it should use the :format option I
> provided, that's what's written in the docs, so if a jpeg is upload, one
> of its style can be a png. And by looking at its source code that's what
> expected to occur.
>
> In dev env it works, but once class caching is turned on, it works once,
> then craps out. I'll see what the devs think about it.
> --
> Posted viahttp://www.ruby-forum.com/.

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