No repro on 67.

Able to reproduce the Issue on latest M-67 67.0.3376.0/10505.0.0 dev-channel Daisy.
Attaching Video for reference.

Reopening Issue

Thanks..!!

Deleted: OnLatestM67.webm 1.4 MB

	OnLatestM67.webm 1.4 MB View Download

Joel's brain dump for anyone else that might pick up this bug:

The delete button listens to 'click' event.
https://cs.chromium.org/chromium/src/ui/file_manager/file_manager/foreground/js/toolbar_controller.js?l=104&rcl=5c5f86f2c1fda2d9ec2b947aa7b44cea985f0d03

The open button has 2 sections in it, the main 'open' listens to 'click', the little arrow listens to 'mousedown' (via MenuButton).
https://cs.chromium.org/chromium/src/ui/file_manager/file_manager/foreground/js/ui/combobutton.js?l=106&rcl=915ec100be7e4ded68283627b8a03fca214e04d0
https://cs.chromium.org/chromium/src/ui/webui/resources/js/cr/ui/menu_button.js?l=126&rcl=915ec100be7e4ded68283627b8a03fca214e04d0

The search text listens for 'blur'.
https://cs.chromium.org/chromium/src/ui/file_manager/file_manager/foreground/js/ui/search_box.js?l=60&rcl=915ec100be7e4ded68283627b8a03fca214e04d0

The order that events are fired by the browser are:
mousedown
blur
mouseup
click

By calling event.prevendDefault(), it is possible for earlier events to stop the following events from happening.

I can't see why, but click is not firing after blur.  Hence the search box closes, but delete or open doesn't trigger.  An alternative is to change delete and open to listen to 'mousedown' rather than 'click'.  The downside for this solution is that blur does not seem to fire then and the search box is left open.

Alex, let me know if you have any thoughts about this bug.

Looks a bit more complicated. I somehow managed to get it to fail for the 'Open' button as well. Try this:
1) Select image
2) click 'search'
3) click 'open'
4) click 'open again.
The open at step (3) fails, then works in (4) so there's something strange going on with retained state by the looks of it. 

I think the behaviour you are seeing is the same that I described.  The first time you click open (step 3), the blur event triggers, but the click event for open does not.  Then when you click open again (step 4), the click event triggers and the open succeeds.