Poor thing.
This sounds like the same thing my pups had last year.
I had to give them antibiotics and stool hardening meds.

I use a similiar method that Logan suggested when
the pills are large. I add butter to the pill,
than shove it in and close the mouth at the same time
I rub a little butter on the front mouth under the nose,
and once the dog licks I know the pills have been swallowed.