Possible Flint in HBP re the Invisibility Cloak?

[gelite67]

No: HPFGUIDX 152238

At the beginning of HBP, DD tells Harry to keep his Invisibility 
Cloak with him at all times and Harry agrees to do it.

Yet, after DD explains they are going Horcrux-Hunting, he instructs 
Harry to go get the cloak.  (Chapter 25)

The text does not say that Harry gets his cloak, but does tell us 
that Harry retrieve the Marauder's Map and Felix from his trunk, 
which he gives to Hermione and Ron.  And, Harry tells them that 
DD "thinks" he is getting his cloak.  Which, to me, implies that 
Harry, in fact, had the cloak all along. 

I'm confused.  I can understand why Harry wanted DD to think he 
needed to retrieve his cloak, but I don't understand why, given that 
DD had instructed Harry to always carry the cloak and Harry agreed, 
why DD didn't ask Harry if he had the cloak or didn't assume that 
Harry had the cloak. Even if Harry didn't have the cloak, we've no 
indication that DD used Occlumency in this situation.

Maybe Harry wasn't wearing his robes and DD knew the robe wouldn't 
fit into his pants?  If so, I wonder why DD doesn't "remind" Harry 
that he promised to keep the cloak with him at all times?

Any thoughts?