It can be done, but requires each accessory have it's own Connectivity group and gender, and yes, it can do it automatically all together once all is correctly setup.
For instance my mechanical joint uses a pipe, a gland, a gasket, bolts, and the fitting, they all connect automatically, each forming a "pair" Connectivity group, for instance, the pipe will be male in the same group as the gland with one side female, the gland, then the second connector of the gland will have a different Connectivity Group and so on, it is just as any other fitting connection, but with multiple Connectivity groups to avoid confusion, and don't use any of the existing groups so it won't get confused by other connectors.
My method is that I draw each part in a piece of paper, assign group names and gender to each and then is easy to follow, it only takes a few minutes if I draw it first.