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After a few tests, moving to Rails 2.3.10 is pretty straightforward.

It breaks one test (@MailHandlerTest#test_add_issue_with_japanese_keywords@), because of the updated TMail (1.2.3 -> 1.2.7) vendor'd in action_mailer. The fixture email doesn't get unquoted at all. I was able to fix it by disabling @TMail::Unquoter.convert_to_with_fallback_on_iso_8859_1@ that is added in 1.2.7.

It seems that deprecations introduced since Rails 2.3.5 can be easily fixed as well.

Locales will be changed to use %{key} instead of {{key}}. All pending translation patches need to be committed before.
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Some of us closed issues related to Rails 2.3.8 (especially ActiveRecord 2.3.8 if I remember correctly). Maybe it would be a good idea to have a look at them when the upgrade is done (#6193, #6218, #6673 at least).

For the i18n upgrade, there's already an open ticket (#6495), pointing to my tiny note in "#5608":http://www.redmine.org/issues/5608#note-18.

If I can help on specific points, let me know.
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Jean-Baptiste Barth wrote:
> If I can help on specific points, let me know.

It would be great if you could make sure that these errors do not occur with 2.3.10.
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It was decided to keep 1.1 using Rails 2.3.5.
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2.3.11 is "out":http://weblog.rubyonrails.org/2011/2/8/new-releases-2-3-11-and-3-0-4
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Upgraded to Rails 2.3.11 in r4904.

We still force i18n 0.4.2 to load before Rails to avoid further compatibility problems with future i18n releases and/or Redmine plugins that use the old syntax.
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Note that Mongrel 1.1.5 does not work anymore with Rails 2.3.8 or later because of 2 bugs respectively in rack 1.1.x and Mongrel 1.1.5.

See "ticket 4690":https://rails.lighthouseapp.com/projects/8994/tickets/4690 in Rails tracker and "ticket 5":https://github.com/fauna/mongrel/issues#issue/5 in Mongrel's.

Until Mongrel 1.2.0 is out, it is required to add a "mongrel.rb":https://gist.github.com/826692 initializer to @config/initializers@.

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Weird. I opened a new defect for this, see #7688

*edit:* s/7668/7688/ sorry..
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relates,Closed,6193,500 error in Issues list
relates,Closed,6218,Search feature is broken
relates,Closed,6673,Error with links of users and projects
relates,Closed,6495,Convert translations to the new format for i18n 4.x
relates,Closed,7688,Redmine's trunk (rails 2.3.11) doesn't work with Mongrel 1.1.x
relates,Closed,7843,Add a relation between issues = explicit login window ! (basic authentication popup is prompted on AJAX request)
blocks,Closed,7516,Redmine does not work with RubyGems 1.5.0