Unfortunately the timing issue aside, even if you could file, unemployment requires that you be able and available for work immediately. If you were dealing with health issues that prevented you from working, that could also be a disqualifying factor. NYS Department of Labor is pretty strict about the able and available requirement. Glad to hear you're feeling better now though!

I'm really sorry to hear about your situation. Unfortunately, everyone here is correct about the timing issue - 2 years is definitely well beyond the filing window for unemployment benefits in New York. The system is designed for people who file shortly after job separation. However, since you mentioned your health has improved and you're looking to get back into the workforce, I'd suggest reaching out to your local One-Stop Career Center (part of the American Job Center network). They often have programs specifically for people who've been out of work for extended periods and can help with job training, resume assistance, and connecting you with employers. You might also want to check if you qualify for SNAP benefits or other assistance programs while you're job searching. Don't give up - there are resources available even if unemployment isn't an option at this point.

UPDATE: I got an official letter in my online inbox today confirming I've been enrolled in Extended Benefits! It explained the additional work search requirements (5 activities per week) and confirmed I'm eligible for 13 more weeks. Thanks everyone for your help with this confusing situation!

Congratulations on getting the official confirmation! This whole thread has been super helpful for those of us dealing with the same confusing situation. I'm still waiting for my letter but feeling much more confident about continuing to certify after reading everyone's experiences. The 5 work search activities requirement is definitely something I need to adjust to - I've been doing the minimum 3 for regular UI. Does anyone have tips for good work search activities that count toward the requirement? I want to make sure I'm documenting the right types of activities.

After dealing with this mess for days, I just want to say that you might wanna check out claimyr.com if you're tired of the hold times. I found it on reddit last month when I had a different issue. Talking to an actual human at DOL got my payment processed right away, worth every penny.

Just wanted to give everyone an update - I finally got my payment this morning! It showed up in my bank account around 6am even though the DOL website still shows "processing." So definitely keep checking your actual bank accounts, not just the website. Hopefully everyone else starts seeing theirs come through soon. Thanks to everyone who shared tips and info, this community is seriously a lifesaver when dealing with DOL issues 🙏

anyone else think it's crazy that in 2023 the default payment method is still these stupid debit cards instead of direct deposit? the whole system is designed to be difficult on purpose.

I went through this exact same situation about 6 months ago and it was incredibly stressful. Here's what worked for me: First, definitely call KeyBank back and use the words "financial hardship" - they have expedited replacement options they don't advertise. I got mine in 3 days instead of 2 weeks. Second, absolutely switch to direct deposit for future payments. Log into your NY.gov unemployment account and update your payment method. It takes about 1-2 payment cycles to kick in, but it's so much more reliable than these cards. For the money already on your lost card - that stays tied to the card account, so you'll still need the replacement to access it. But some people have had luck going to a KeyBank branch with ID to get emergency cash access. If you're really struggling to get through to anyone by phone (which is super common), your local state representative's office can sometimes help cut through the red tape. They have direct contacts at the unemployment office that regular people can't reach. Hang in there - the system is frustrating but there are ways to get your money. The direct deposit switch will save you from this headache in the future!

For everyone reading this thread with similar issues: If you're currently receiving NY unemployment benefits and want to avoid this situation next tax season, call NYSDOL and request both the federal Form W-4V to increase your federal withholding above 10% AND the NY State Form IT-2104-E for state tax withholding. Don't assume the default withholding will be enough, especially if you have other income sources during the same tax year.

I'm so sorry you're going through this! The same thing happened to me when I was on unemployment a few years ago. It's incredibly frustrating because they make it seem like having taxes withheld means you're all set, but that 10% federal withholding is nowhere near enough for most people. I ended up owing about $800 that I wasn't expecting at all. One thing that might help - if you can't pay everything right away, both the IRS and NY State offer payment plans that aren't too bad. The IRS lets you set up an installment agreement online, and NY has similar options. At least that way you're not hit with huge penalties while you figure out how to pay it off. It's not ideal, but it's better than ignoring it and letting the penalties pile up. Also, I learned my lesson and now always set aside extra money if I ever have to go on unemployment again. The whole system really needs to be clearer about this stuff!