Visio Guy

I drew two rectangles and added one connection point to the left of each. Assigned outward and inward behavior. Everything is OK-they glue. After that, I added one more connector point to the top of each rectangle and assigned outward and inward behavior too. Now only one of the points glues.

Set their type to 2 (inward + outward)

I tried all cases but can`t glue top glue pt of the bottom shape to the bottom glue pt of the top shape.

Check the attachment

Cant do that (glue multiple shapes together with connection points)....never ever worked 2003 onward
You CAN do multiple  connectors a shape or between shapes (1 to 2...1 to 3....1 to 4...2 to 3...2 to 4)
 
(I spoof this by using Junes work to make a connector with N lanes....so looks N connectors...but really just 1 between shapes0

If you could (true shape to shape), one could truly build a lego system here.

you can emulate this behavior to some degree by use the shapesheet function loctoloc

this shape pinx, piny=guard(loctoloc(pnt(othershape_pinx+deltax, othershape_poiny+deltay),othershape.width, this shape width))
deltax =1/2 width of other shape
deltay = 1/2 height of other shape

repeat as needed (tedious or automate)

now you can drag shape 1 every where and shape 2 and 3 follow
shape 2 and 3 can NOT be the leader...only followers of other shapes

@Vojo, test the file I uploaded. The small shape is glued to the bigger one.