Fee Waiver Question

Hey everyone,
I’m a prospective transfer student who made a relatively late decision to apply for admissions to Dartmouth. I checked off that I need my application fees waived on the Common App, and my academic advisor is aware of this. However, he does not know I’m applying to Dartmouth, and I’m hesitant to share this with him because he can be a little rude, especially when it comes to my transfer application process. It’s not that I don’t want him knowing about where I’m applying, I just don’t want to deal with the sass for not telling him I’m applying to Dartmouth.
My question is: How does Dartmouth notify advisors that they need to verify a student has a need to have the fee waived? Do advisors get an email from the Common App saying to verify this or does Dartmouth notify them directly? I just want to be prepared for any judgments, since he’s not entirely supportive of me applying to other schools either, and based on my research on this topic, not all schools contact counselors/advisors for the need verification in the first place.
Thank you!

Questions:

How are you suppose to get your fee waiver approved?
Who is responsible for uploading your transcript?