I was stuck in the MSP storm last Monday, 7/15, and I submitted a request for delay verification the next day, 7/16. I haven't heard back yet, coming up on close to a week now.

How long does this process usually take? I need to make a claim on my trip insurance, so this is a requirement for me. I have called twice and the representative's do not seem to know what I am asking for, but times they have sent me incorrect info, first it was just a flight verification, and the second time was just a receipt, not what I needed at all.

Did you submit a request via "Contact US" email?
That usually works best.
If you have a Skymiles account and therefore an associated email, often there's a proactive email about a day after the email which worked well for the delay insurance claim.

I've also taken screenshots of the flight status which also shows the delay and actual arrival time.

Ok, I've never used travel insurance, so I can't help. But is it really necessary for you to get verification from airline? I'm pretty surprised the insurance company isn't able to verify this themselves

Yes, I did a recent delay claim via my Chase SR card and they wanted proof from the airline. But my Delta apology (which also had given me some miles) was sufficient for the claim. We also had a delayed baggage claim as well, though eventually didn't need it since Delta reimbursed for everything themselves.

FYI, the company that services the CSR claim was fast and easy, plus they ended up looking at all the details and even though I didn't give them all the documents they wanted to prove my domestic partner relationship, accepted what I gave and the statement I made.

Was pretty easy and satisfied with the process

I didn't use Contact Us, I used their Delay Verification form, here. Is there a better way?

For the CSR insurance it is definitely required.

Interesting. Seems like they could save a fortune if they just learned how to use flightaware or any number of similar sites. I guess maybe they don't want to make the claim process TOO easy, adding a paperwork burden might help to discourage some people from filing.

FWIW—and this was with Citi's program, not Chase's—the terms said that they strictly needed delay verification from the airline. I just submitted a pdf of the flight status from Flight Aware and that worked fine in lieu.

Correct. Most of the decent insurers no longer require, at least in the first instance, proof of anything because they collect all of that data directly (not that one couldn't do this through a manual process as well).

But, by inserting a step, some percentage of people will forget, won't bother, or otherwise drop the ball. As an insurer, that's a good thing.

What is the "Contact Us" email for Delta? Is it the "Submit a Compliment/Complaint" one?

They cannot get my delay verification correct. Here is what happened:

DL1411 SFO>MSP was delayed 18 minutes on 7/15 due to MSP weather. Had a 45 minute connection, before any issues. Landed late and was in G gate, connection DL3310 (ended up leaving roughly 2 hrs late) MSP>DSM was at B gate. Wife is 7 months pregnant, ran as fast as we could. 3310 was delayed 45 minutes due to WX, but one gate down DL3465 was finishing up boarding because they were also delayed. It had empty seats, and since we were on a F award ticket, we switched over to that flight. Boarded, sat for 30 minutes, then crew timed out. Deboarded plane, and was rebooked onto DL3867 the next day, 7/16, 9:06AM departure. Woke up, 3867 was delayed until 1:00PM. Finally got to DSM around 16 hrs after scheduled arrival.

I have explained this to at least 4 phone agents, and every time they send me "Flight verification" emails, and the emails do not show that I was delayed. They only show either the 18 minute DL1411 delay, or that DL3310 delay of roughly two hours.

Who is the best place to contact for this?

If you make a completely voluntary change, and because of that decision you end up being significantly delayed, can you claim for the delay?

I mean, this was obviously not your intention, but if people are allowed to make last-minute voluntary changes and then claim insurance, it would be easy for someone to get to the airport, find a flight to any hub that is delayed, switch to that flight, and then file a claim.

You purchased insurance for your itinerary. If you had traveled on your itinerary, you would not have needed to make a claim. You made a smart decision that backfired badly. Presumably you didn't consult with the insurance company before making that decision.

Seems like you should submit proof that DL3465 was cancelled (and then attach an explanation of why that matters since you weren't actually booked on DL3465)