Sadly, he was staying at the veterinary hospital I worked because he suffered from something called “megaeophagus”; basically, his esophaeus was stretched out and every time he ate his food would get stuck and he would vomit.
The vet I worked for hit upon an innovative solution to fix this; we fed him tiny, easy to digest meals from an elevated surface so that he could keep the food down. It worked, and Olaf went home a happy dog.
It turns out that Starship here and why yes, that is the cutest name for a puppy with those ears ever has the same condition, and the solution? Eating in a high chair.