Hello Juan Jose and Sami,
I have the same problem, if it helps, in my case I use 4 levels of custom urls, example:
/level-0/level-1/level-2/level-3
I have the next plugins:
“Redirection” John Godley
“Remove Category URL” Valerio Souza, WordLab Academy
I also do not have a development server, but I will try to investigate a little and if I can find something, I will comment here.
Thanks again Sami!