Why does TortoiseSVN delete always cause a conflict?

Question

I click TortoiseSVN->Delete. Then when I commit I get the following error:

Deleting: C:\00.Source\Code\trunk\Folder\Database\FileToDelete.something  
Error: Commit failed (details follow):  
Error: The MERGE response contains invalid XML (200 OK)  

I commit again and get:

Deleting: C:\00.Source\Code\trunk\Folder\Database\FileToDelete.something  
Error: Commit failed (details follow):  
Error: File  
Error:  'C:\00.Source\Code\trunk\Folder\Database\FileToDelete.something'  
Error:  is out of date  
Error: '/svn/Apps/!svn/wrk/fdsafasfdasdf/Code/trunk/Folder/Database/FileToDelete.something'  
Error:  path not found  
Error: Additional errors:  
Error: DELETE of  
Error:  '/svn/Apps/!svn/wrk/fdsafasfdasdf/Code/trunk/Folder/Database/FileToDelete.something':  
Error:  404 Not Found  
Error: You have to update your working copy first.  
Completed!:   

I update and get:

Updating: C:\00.Source\Code\trunk\Folder\Database  
Tree conflict: C:\00.Source\Code\trunk\Folder\Database\FileToDelete.something  
application/octet-stream
Completed: At revision: 51624  
Warning!: One or more files are in a conflicted state.  

And then I have to click resolve and it is all ok. Am I doing something wrong?

I am still on 1.8.0 because of a previous issue here: TortoiseSVN Won't Allow Me To Add Any Files, but I don't think that's the problem.