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So Buddy’s pills are to be administered every 3-4 times a day as needed. Meaning like a 6 hour pill. However, it seems that the pill I gave him at 4:30 must have worn off around 9:00 as he started coughing again. 

Not wanting to OD Buddy on cough tabs, I waited until 10pm, but it took until 11 for him to be able to finally fall asleep.

He has been sleeping peacefully on the floor near the desk for at least 45 minutes. 

I hope it lasts all night, but I expect him to wake me around 3am again.