Difficulty with LOR writer

Hello all,

Applying through TMDSAS this cycle and had planned to have 4 letters of recommendation. Notified all my letters writers weeks ahead of time. 3 of the 4 got theirs into Interfolio early, one didn’t submit until it was pretty late and didn’t sign it, no letterhead, etc. So I had to contact the letter writer and go over the requirements with them multiple times. He finally submits it with Interfolio checking it and saying it looks good. Now TMDSAS has rejected it because he didn’t date the letter. I genuinely believe it will be a very strong letter, he just seems to have difficulty following the instructions on writing it. I am grateful for the letter, but should I just cancel the letter with TMDSAS, rather than wait weeks for him to finally send it again and then have it processed by TMDSAS? This letter is basically the only thing holding up some of my secondaries from being complete at this point.

Any advice is infinitely appreciated.

I hope someone aside from me replies with a more informed response, but I can give my personal thoughts.

Do you need the letter?
If not, drop it like a hot potato.
If so, set up an in-person meeting with the writer regarding the letter (no need to get detailed when setting the meeting). Make sure it happens within the next week. At the meeting, explain the problem, and ask if you can complete it together right there since the time in their calendar is already blocked off. You don’t need to see it, but they can pull it up and go through each of the requirements as you read it off (i.e., “Date?” “Yes.” “Signature?” “It’s there.” “Alright, is it on letterhead?” “Yup.”). It might feel tedious to everyone involved, and handholding is not the method of greatest professional interaction, but it is sometimes necessary to meet deadlines and standards that only 1 party really gets but the other party needs to follow through on.