Our first doxie had wicked anal gland issues and both were on a grain free diet. I think some dogs just have them worse than others although diet is the first issue that comes into play, IMO, when anal glands are involved. I would start by adding pumpkin as suggested in previous posts - it does work! Check the fiber content of your puppers food and treats. With normal anal glands, a good solid poo will clear them out. I can see them release with our 2nd doxie who we still have - with Brodie, I'd have no chance at seeing anything.
I expressed our doxies anal glands; it's too expensive when you have a dog with issues and really easy, although super gross. I would take 2 ziploc bags, inside out, use them for my glove/collection/containment. I would always express outdoors no matter the time of year. Have wipes ready. If you get them in the morning when they still have to poo, I find it is easiest as there is internal stuff already wanting to come out. When you express, it goes into the inner ziploc bag, you zip up both bags and toss. The anal glad smell is that of aging, rotting tuna fish - best for outdoors, no skin contact, prior to a bath. I never expressed on a regular basis as I do believe it interferes with how the dogs system is supposed to work on it's own - I only did as needed. You will instantly recognize that awful odor creeping back in and know it is time.
Both Brodie, our sheltie, and Kooper, our remaining doxie, are on Fromm's Gold Adult - I can see Kooper's glands empty at times when he poos so I know things are working a-okay. We lost Buddy, the first doxie, years ago and I, thankfully, have not had to express glands since.