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I think SVN is trying to cache the server certificate and failing to do so.

It may be trying to cache to the Keychain, in which case you should try unlocking your keychain and doing an 'svn up' in one of stacks that is versioned with svn. Repeated attempts to 'svn up' in the same directory shouldn't ask you to accept the certificate any more.

On the other hand, it may be trying to cache to ~/.subversion/auth/ , in which case you should make sure that directory exists and that your user has write permissions to it. See also: http://www.linxit.de/svnbook/en/1.1/svn-book.html#svn-ch-6-sect-4.3.2