Open Can't send file to android from google chrome extension?

howdy all,
I'm having issues with sending files to my android devices. I've tested it several different ways, this is what I figured out so far.

From my chromebook sending files via chrome extension to android works
From my windows laptop using the Windows app sending files to android works

BUT

From my windows laptop using the chrome extension to android, it does not work.

It says uploading but then never downloads/launches in the android devices.

anyone have this experience?

 

Was out of town for a while on a trip but getting back to this now. Thanks for replying!

I checked, they're all definitely using the same gmail account.

BUT I did notice the Windows Chrome Join extension shows the proper account but says "This device: undefined".

So I remved the extension from my windows chrome (and noticed it automatically removed from my chromebook chrome browser too immediately). I reinstalled it and logged in with same account. Weirdly both chromebook and windows chrome browsers show up as This device: undefined now. So, even more confused.....