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Yuki Nakamura

How to upload documents for unemployment verification on my.ny.gov - system keeps rejecting files

I've been trying to upload documents for my unemployment claim verification for the past two days and the my.ny.gov system keeps giving me error messages. I need to submit my separation notice and ID verification but every time I select the files and hit upload, it either says 'file format not supported' or just times out. I've tried JPEGs, PDFs, even took photos with my phone - nothing works. Has anyone else had this problem with uploading documents to NYS Department of Labor? I'm worried my claim is going to get delayed because of this technical issue.

I had the same problem last week! The file size limit is really small - like 2MB or something. Try compressing your PDFs or making sure your photos are under that limit. Also make sure the file names don't have any special characters or spaces in them. The system is really picky about that stuff.

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Oh wow I didn't know about the file size thing! My separation notice PDF was probably way bigger than that. Let me try shrinking it down and see if that works.

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The my.ny.gov upload system is notorious for being glitchy. Here's what worked for me: 1) Use Chrome browser only, 2) Clear your cache and cookies first, 3) Make sure files are under 2MB, 4) Use PDF format for documents, JPEG for photos, 5) Try uploading during off-peak hours like early morning. The system gets overloaded during business hours and weekends.

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This is super helpful! I was using Safari and having the same issues. Switching to Chrome fixed it for me too.

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ugh this system is so frustrating!! ive been trying for WEEKS to upload my stuff and it never works. why cant they just let us email documents like normal people???

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I know it's annoying but they have to use the secure portal for privacy reasons. If you're still having trouble after trying the file size/browser fixes, you might need to call NYS Department of Labor directly.

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I was stuck on this for days until I found out about Claimyr. It's a service that helps you get through to actual NYS Department of Labor agents on the phone - they can sometimes accept documents through alternative methods or walk you through the upload process step by step. Check out claimyr.com, they even have a video demo at https://youtu.be/qyftW-mnTNI showing how it works. Saved me hours of frustration with the online system.

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Interesting, I've never heard of that service before. Is it legit? I'm desperate at this point so anything that might help would be great.

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Yeah it's totally legitimate. They basically help you skip the hold times and get connected to real people at NYS Department of Labor who can actually solve problems. Way better than sitting on hold for hours.

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Just wanted to say thanks for posting this! I was having the exact same problem and the file size tip worked perfectly. Sometimes the obvious solutions are the ones we miss lol

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Another thing that helped me was making sure I was logged out and back into my.ny.gov completely before trying to upload. Sometimes the session gets corrupted and you think you're logged in but the upload function doesn't work properly. Also, if you're scanning documents, try scanning at 150 DPI instead of higher resolution - it keeps the file size down but still maintains readability for the reviewers.

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I had this exact issue last month! What finally worked for me was using a different device entirely - I was trying on my laptop and it kept failing, but when I switched to my phone using the mobile browser, the uploads went through perfectly. Also make sure you're not using any browser extensions that might be blocking the upload - I had to disable my ad blocker temporarily. The my.ny.gov system seems really sensitive to anything that might interfere with the upload process.

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That's really interesting about switching devices! I never would have thought of that. I've been banging my head against the wall trying to get this to work on my desktop computer. Going to try uploading from my phone right now - hopefully that does the trick. Thanks for the tip about browser extensions too, I definitely have a bunch of those running that could be interfering.

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I just wanted to add my experience since I ran into this same issue recently. After trying most of the suggestions here (file compression, Chrome browser, etc.), what finally worked for me was actually logging into my.ny.gov through a completely fresh browser session - not just clearing cache, but literally using a browser I'd never used to access the site before. I also discovered that if you have any VPN or proxy services running, they can interfere with the upload process. Once I disabled my VPN and used Edge browser (which I never use for anything else), the documents uploaded on the first try. It's like the system has some weird conflict with browsers that have any history of accessing the site. Worth trying if you've exhausted the other options!

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That's such a smart approach! I never would have thought to try a completely fresh browser that's never accessed the site before. The VPN interference issue is really interesting too - I do have a VPN running most of the time and didn't consider that it might be causing problems with the upload process. I'm going to try Edge since I never use it for anything, and I'll make sure to disconnect from my VPN first. It's crazy how finicky this system is, but I really appreciate you sharing what actually worked for you!

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I'm going through this exact same nightmare right now! Been trying to upload my documents for unemployment verification and the system just keeps rejecting everything. Thank you all for sharing these detailed workarounds - the official help page is completely useless and just says "try again later." I'm going to work through these suggestions systematically: starting with Chrome browser, compressing files to under 1MB, simple file names with no spaces, and trying during early morning hours. It's absolutely ridiculous that we have to become tech experts just to submit basic documents, but I'm so grateful this community exists to share real solutions. The my.ny.gov system is clearly broken but at least now I have a game plan instead of just randomly trying the same thing over and over. Will definitely update once I (hopefully) get through!

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You're absolutely right that the official help is useless - I went through the same frustration! The systematic approach you outlined is perfect. One thing I'd add is to make sure you're completely logged out and back into my.ny.gov before trying the upload process. Sometimes the session gets stuck even though it looks like you're logged in. Also, if you have any browser extensions running (especially ad blockers or privacy tools), try disabling them temporarily - the upload system seems really sensitive to anything that might interfere. The early morning timing really does make a huge difference! Good luck and definitely let us know what combination works for you.

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This is such great advice! I never thought about the session getting stuck even when it looks like you're logged in - that could definitely explain some of the weird behavior I've been experiencing. I do have several browser extensions running including an ad blocker, so I'll make sure to disable those before attempting the upload. The combination of all these community tips gives me so much more confidence than just blindly trying the same broken approach over and over. Really appreciate everyone taking the time to share what actually worked instead of just complaining about the system!

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I'm dealing with this exact same issue right now and this thread is a lifesaver! I've been stuck for days trying to upload my separation documents and was getting so frustrated. Based on everyone's suggestions, I'm going to try a systematic approach tomorrow: Chrome browser in incognito mode, compress everything to under 500KB, simple file names like "separation.pdf" with no special characters, upload around 6-7 AM, and wait 2 minutes between each attempt. It's crazy that we need a whole strategy just to upload basic documents, but I'm so grateful everyone shared what actually worked instead of just complaining. The my.ny.gov system is clearly broken but at least now I have hope and a real action plan. Will definitely report back on my results - fingers crossed!

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Your systematic approach sounds perfect! I just want to add one more tip that helped me - if you're scanning physical documents, try scanning them as black and white PDFs instead of color. This keeps the file size even smaller and the system seems to process them faster. Also, double-check that your documents are crystal clear and readable before uploading - sometimes the reviewers will reject blurry scans even if they upload successfully. The 6-7 AM timing really is crucial, and don't get discouraged if it takes a few tries even with all the right steps. This broken system has taught us all to be way more patient than we should have to be! Looking forward to hearing your success story soon.

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I'm having the exact same problem right now! Been trying for three days straight and getting so frustrated. Reading through all these solutions gives me hope though. I'm going to try the combination approach: Chrome browser, compress files to under 500KB, simple naming like "id_doc.pdf", and upload early morning around 6 AM with 2-minute waits between attempts. It's ridiculous that uploading basic documents requires this much troubleshooting, but I really appreciate everyone sharing what actually worked instead of just the generic "contact support" responses. The my.ny.gov system is clearly broken but at least now I have a real game plan to try. Will definitely update with results - thank you all for the detailed advice!

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I'm so glad you found this thread helpful! I was in the exact same boat just a few weeks ago and felt completely lost until I discovered all these workarounds. Your systematic approach sounds spot-on - the combination of Chrome browser, ultra-compressed files (500KB is definitely the sweet spot), simple naming, and early morning uploads really does make all the difference. One small addition to your plan: make sure to fully close and reopen your browser before starting the upload session, not just clear cache. Sometimes there are hidden background processes that can interfere. The 2-minute wait between attempts is crucial too - I know it's tempting to rush but the system definitely punishes impatience! Don't get discouraged if it takes a couple tries even with all the right steps. You've got this, and we're all rooting for you to get through this broken system!

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I'm experiencing this exact same issue right now! I've been trying for almost a week to upload my ID verification and wage statements, and the my.ny.gov system keeps failing. This thread is incredibly helpful - I had no idea about all these specific technical requirements. I'm definitely going to try the systematic approach everyone's recommending: Chrome browser in incognito mode, compress everything to under 500KB, simple file names without spaces, upload during the 6-7 AM window, and wait at least 2 minutes between attempts. It's absolutely mind-boggling that such a basic government function requires this level of troubleshooting, but I'm so grateful this community exists to share real solutions. The official help documentation is completely useless compared to all the detailed advice here. Going to set my alarm early tomorrow and work through these steps methodically. Really hoping this works because I'm worried about my claim getting delayed over these technical glitches!

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You've got exactly the right strategy! I went through this same nightmare just a couple weeks ago and that systematic approach is what finally got me through. One additional tip that really helped me - when you're compressing your files to under 500KB, try to aim for around 300-400KB if possible. I found the system handles smaller files much more reliably. Also, make sure your internet connection is super stable during those early morning uploads - I actually switched from WiFi to ethernet cable for the upload attempts just to eliminate any connection hiccups. The waiting between attempts is so important, even though it's torture when you just want to get everything submitted! Don't worry about your claim getting delayed - as long as you're making good faith efforts to upload (which you clearly are), they usually give you some leeway for technical issues. You're going to get through this!

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