Why can't I get inside the grandfather clock in this time?

Hint 1 of 15:

Purple Tentacle's orders are preventing you.

Hint 2 of 15:

Or rather, the guard who has to carry out those orders is.

Hint 3 of 15:

His main job, though, is to take care of escaped humans.

Hint 4 of 15:

There are some humans in the kennel.

Hint 5 of 15:

But before you can do anything with them, you'll have to take care of the
"Mr. Tentacle Guy" who's in charge of them.  See the next question if you
don't know how to get rid of him.