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Hello, this is Dr. Jess. I am sorry to hear about your pup. It sounds like he likely has a torn toe nail. These can often happen in dogs with long toe nails. To treat the torn toe nail, we usually place some numbing drops on the area, and attempt to remove the torn portion. Sometimes the nail is just barely attached to the quick and will easily come off with a little tug. Other times they are more firmly attached. The loose portion of the nail needs to be removed, the area cleaned, and a bandage applied for a few days to protect the area. Sometimes based on the severity we may also prescribe an antibiotic and a pain medication. This isn't a life threatening emergency and can wait until the morning to be treated.