In my case, the Glassware is inserting a jpeg image as a timeline card as a response to User's Voice query using "Take a note" Voice command. I keep waiting sometimes 10-15 mins before I see that timeline card on Glass. Sometimes, I see the inserted timeline card on Glass device only after I reboot the Glass device.
The way I have implemented this is:- I do the Boot-strapping, that also includes inserting my Glassware Contact that accepts Voice command "Take a Note". Then on Glass I make a voice query using "Take a note", my Glassware accepts that query, sends an OK message to the Mirror Service and then inserts a new Timeline with jpeg image.
The Glass displays the Voice query however, it is not able to receive the inserted Timeline card in a consistent way.