We used to use Collabnet SVN/Apache combo on a Windows server with LDAP authentication, and whilst the performance wasn't brilliant it used to work perfectly.

After switching to a fresh Ubuntu 10 install, and setting up an Apache/SVN/LDAP configuration, we have HTTPS access to our repositories, using Active Directory authentication via LDAP.

We're now having a very peculiar issue. Whenever a new user accesses a repository, our SVN clients (we have a few depending on the tool, but for arguments sake, let's stick to Tortoise SVN) report "Error 500 - Unknown Response". To get around this, we have to log into the repo using a web browser and navigate 'backwards' until it works

E.G:

1. SVN Checkout https://svn.example.local/SVN/MyRepo/MyModule/ - Error 500 (bad)
2. Webbrowse to https://svn.example.local/SVN/MyRepo/MyModule/ - Error 500 (bad)
3. Webbrowse to https://svn.example.local/SVN/MyRepo/ - Error 500 (bad)
4. Webbrowse to https://svn.example.local/SVN/ - Forbidden 403 (correct)
5. Webbrowse to https://svn.example.local/SVN/MyRepo/ - OK 200 (correct)
6. SVN Checkout https://svn.example.local/SVN/MyRepo/MyModule/ - Error 500 (bad)
7. Webbrowse to https://svn.example.local/SVN/MyRepo/MyModule/ - OK 200 (correct)
8. SVN Checkout https://svn.example.local/SVN/MyRepo/MyModule/ - OK 200 (correct)

It seems to require authentication up the tree, starting from the svnparentpath up through to the module required.

Has anyone seen anything like this before? Any ideas on where to start before I ditch it back to Collabnet's SVN server?