I have no idea the answer to your question but I can definitely understand how frustrating it would be! My loans were with Nelnet for a while and I found the CSRs to be quite helpful. I would gather all of your supporting documentation and give them a call.
Sorry I couldn't me more helpful!
You and I share the same previous student loan servicer: NelNet.
As you know, NelNet is a hard nut to crack when it comes to retroactive
forebearance and goodwill requests. They have two (2) very strict criteria:
1) you had to be enrolled as a student at the time, and/or 2) you were on
active military duty. If you fall outside these criteria, they refuse to budge.
I know, I know. It's VERY frustrating! In my case, I was in a gap year between
my bachelors and masters. While evaluating masters programs, I lost track
of my student loans and didn't pay attention to them. As a result, I got 5
months behind on my loans. And like you, I thought I had one loan with
NelNet. But as it turned out, I had 6! So I had 6 different 150 day lates
dragging down my scores. I worked out a repayment program with NelNet,
and my scores skyrocketed over 90 points by doing so because all the loans
started reporting as paid as agreed. But unfortunately to this day, NelNet still
refuses to remove/forgive/goodwill/retroactively forebear my 150 day lates.
So I took some really good advice from a student loan specialist here in the
MyFICO forum and consolidated my loans with Great Lakes. If you do a search
in the forums, you'll find that Great Lakes has an exemplary track record of
granting GW requests and retroactive forebearances to their customers.
And the best thing about consolidation is that the loans will report as
"Paid in Full by Consolidation" to all 3 CBs. So my scores will rise again.
What I'm not sure of is if NelNet will retroactively forebear my lates
once the loans are paid off. If past is prologue, then the answer is No.
So Yes, I'm sort of in the same boat as you. And even if you and I both
move forward exactly as things stand with our loans, there's still no
guarantee that NelNet will grant a retroactive forebearance on our lates.
What I'm saying to you may or may not help you solve your problem.
But I want you to know that I know exactly how you feel.