File your claim immediately after your last day of work and clearly explain the medical necessity. Include your doctor's statement with your initial application if possible. During adjudication, they'll review whether your reason meets the 'compelling personal reason' standard. Don't wait to file - you can't get benefits for weeks you don't claim even if approved later.

Have you looked into New York's Paid Family Leave (PFL) program? Since you're dealing with pregnancy complications, you might be eligible for both disability benefits during your recovery period AND paid family leave after the baby is born. PFL provides partial wage replacement for up to 12 weeks. You should definitely explore all your options - unemployment, temporary disability, and PFL - since they each cover different situations and time periods. The NY Department of Labor website has a benefits advisor tool that can help you figure out which programs you qualify for based on your specific circumstances.

Just want to add - make sure the contract work doesn't interfere with your job search requirements. You still need to be doing your required work searches even while working the contract, unless NYS Department of Labor specifically waives that requirement for your situation.

Another important consideration - since this is web development contract work, make sure you understand how NYS Department of Labor handles self-employment income. As a 1099 contractor, you're technically self-employed for those weeks you're working. If you're working full-time hours on the contract (even if it's temporary), you might not be eligible for benefits during those weeks regardless of the income amount. The key is whether you're "totally unemployed" vs "partially unemployed" during each claim week. I'd recommend calling to clarify your specific situation before starting the contract.

Have u tried the callback option on the website? I did that and they called me back... 3 weeks later 🙃 but at least it worked eventually

I'm dealing with the exact same issue right now - filed my new claim in October and still haven't seen a dime. The automated system is absolutely brutal. What's helped me is trying the claimyr service that others mentioned AND calling the TTY line. Also found out there's a special reapplication escalation number if you google "NY unemployment reapplication phone number" - it's different from the main line. I'm also going to try that callback option someone mentioned because at this point I'll try anything. The stress is unreal when you're waiting on money you're legally entitled to 😤

I'm going through something similar right now and called the NYS Department of Labor directly last week. The representative confirmed that you cannot get benefits for weeks before you filed your initial claim. The system is pretty rigid about this - your benefit year officially begins the Sunday of the week you submit your application, regardless of when you actually lost your job. I know it's frustrating when you're already dealing with job loss stress, but the lesson I learned is to always file immediately even if there's a chance of getting rehired. You can always cancel or pause your claim if your situation changes, but you can't go backwards to claim those earlier weeks.

I learned this the hard way too when I was laid off a few years ago. The NYS Department of Labor is very strict about this rule - your benefit week starts from the Sunday of the week you file, period. I waited almost a month thinking my employer might rehire me and ended up losing out on nearly $1,200 in benefits. The system doesn't have much flexibility for individual circumstances, unfortunately. My advice for anyone reading this is to file your claim the day after you lose your job, even if you're optimistic about getting called back. You can always withdraw or stop certifying if you get rehired, but you can't recover those lost weeks. It's one of those bureaucratic rules that seems unfair but is consistently enforced.

Yes definitely mention your job search activities when you file! Keep records of everywhere you applied, any interviews you had, etc. NYS Department of Labor wants to see that you were genuinely looking for work even if you weren't claiming benefits yet. This documentation could help support your case for backdating some of those missed weeks.

I went through this exact same situation about 8 months ago - waited 5 weeks thinking I'd land something fast. Here's what I learned: file TODAY, don't wait another day. When you file, there's a section where you can explain why you delayed filing. Be honest about job searching but emphasize any specific circumstances (like if you had interviews lined up, were waiting on a specific opportunity, etc.). I was able to get 3 out of my 5 missed weeks approved by showing my job application emails and interview confirmations. The key is having documentation of your active job search. Also, once you file, you'll need to certify weekly going forward, so the sooner you start that process the better.