What a coincidence (or sign that our community is big): I was fighting
the same problem yesterday.

I found that I could more reliably track the root cause by leaving
config.cache_classes alone and instead settting

  config.reload_plugins = true if RAILS_ENV == 'development'

***in environment.rb (not in development.rb***

I resolved my problem by cleaning up plugin code to do less "require"
and more auto-loading.  I moved/renamed files to match Rails'
autoloading expectations.

For testing, use the console and try "reload!"  I was fortunate in
that I would get a shower of sparks every time I tried "reload!" until
things were clean.  Once cleaned, I reset reload_plugins to false
(just deleted the above line actually).

Also, there is a high correlation between the "Can't dup NilClass"
error and the "A copy of XX has been removed from the module tree but
is still active!"  In my case, solving one solved the other.  And
which one appeared had something to do with the config settings.

Good luck!

-Chris

On Sep 15, 8:01 pm, Luke <[email protected]> wrote:
> I'm having the same issue discussed 
> herehttp://groups.google.com/group/rubyonrails-core/msg/787b561d166abf53
>
> As reported elsewhere, in 2.3.2, the "Can't dup NilClass" error pops
> up on the second request to a page, after a server restart. It seems
> esp. "buggy" considering that you can bypass the error consistently by
> setting config.cache_classes = true in development.rb (as in prod &
> test environments).
>
> Anybody found a solution for this?
>
> Luke
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