This code on Windows using ActiveTcl 8.4.1:
toplevel .foo
toplevel .moo
update idletasks
wm transient .moo .foo
grab set .moo
toplevel .boo
update idletasks
wm transient .boo .moo
grab set .boo
toplevel .bar
update idletasks
wm transient .bar .boo
grab set .bar
Creates the proper windows. Then, double-click the
taskbar, iconifying the application. Now, click the
taskbar icon again, deiconifying the application.
Every window except the top one, .bar, come back. The
state of .bar is still withdrawn for some reason. And,
if you attempt to deiconify it, it draws the title bar
and an outline of the window but never finishes. It
hangs there.
This problem (specifically, that .bar is never redrawn anymore) appears to affect Tk 8.5.9 on Windows 7 and Tk 8.6b2 on an unreported version of Windows. I believe I've traced it as far as WM_PAINT events not arriving in TkWinChildProc for the window.
Second test was Tk 8.6b2 / WinXP
The script that I developed before finding this tracker item was:
package require Tk
wm dei . ; wm geo . +100+100
toplevel .t ; wm geo .t +100+500
toplevel .s ; wm geo .s +500+100
toplevel .u ; wm geo .u +500+500
wm trans .t .
wm trans .s .t
wm trans .u .s