My pup has developed a habit of needing her glands expressed pretty often. We just do it ourselves because I had to do it for my border collie daily after she became paralyzed so it's no biggie, really. We called the vet after the first time and they said just to increase her fiber and express as needed. They led us to believe that it just happens to some dogs. especially small ones and mines only 7.4 lbs full grown. We did add fiber, to be exact Earth's Best Organic pumpkin apple baby food at each meal. Like it said, it doesn't even bother me to do it. Nothing in her food could be causing this-she's eating organic boiled chicken with organic veggies at a 2:1 ratio while waiting for her Paw Naturaw chicken patties to get here and she has perfect stool on her homemade diet. SO is this just going to be a permanent thing? Or is there something else to do? She's 8 months old and it started not too long ago. I don't give her grains so I can't feed her oatmeal or anything

Yes - but only because they are not on the right diet, so their stool are not 'normal'. These glands should never be empty - they are scent glands and should express just a small amount of 'fluid' with every normal stool passing. Once you get your puppy onto a feed that allows her to have a normal stool (and bulk matters too), the need to be expressing her glands should stop. When dogs have periods of looseness, or even constipation, these glands become clogged, which is when infection can set in too. If what you get out when you do express them yourself, is at all dark, or thick, you do need your vet to check it, and probably prescribe antibiotics to clear up any infection that might be going on. Worse possible with this is the glands could rupture. My vet used to empty these glands if I felt there was a problem (I can do this myself too), and pack them with antibiotic which cleared things up fast. pets question and answers,www.5d2d.com

Just know, the more you play with these glands, the more often you'll have problems - they are not supposed to be empty and if you do empty them, they will fill up again.