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I was associating your response with both our posts, since you mentioned that intricacies of the camera did not matter, which went to my question, but had not mentioned that you had disconnected the camera.
So, the Flex is what sees a difference between the flash and the CC/CST. Take a bit of scotch tape, cover the four small additional connections on the hotshoe adapter, try the flash again.
My bet is that the flash will not fire in this case, meaning it is somehow making use of those connections to determine that there is something in place to send a test fire signal to.
Since you can fire the CST by shorting the connection, you know the connection itself is good, so the TT5 must not be sending the signal. You know the TT5 is capable of sending the signal because when you put a flash in the adapter, it fired.
So the TT5 is, for some reason, not sending the signal when a CST is installed. Covering those contacts would prove whether or not they are a factor in this. If you have a cheapo flash, with only the center contact, you could also try it out, see if it fires or not.
(an aside: David Hobby recently discovered and posted that covering certain hotshoe contacts with scotch tape would allow the d7000 to fire a nikon flash at any speed, rather than limiting it to synch speed in normal mode. the dark band is not always a factor, so he wanted a way around that firmware limitation. kinda cool)
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