I experienced something very similar with Free File Fillable Forms just a few weeks ago! The password field clearing with no error message is incredibly frustrating. After reading through all these suggestions, I'd recommend trying them in this order: 1. First try the simplest solutions - incognito/private browsing window and manually typing your password instead of copy/pasting 2. Check if you're using a VPN and temporarily disconnect it 3. Try the "Forgot Password" reset even though you know your password - this seems to fix authentication glitches 4. Clear cookies specifically for irs.gov and freefile.intuit.com domains 5. If you have antivirus software, temporarily whitelist the Free File domain What ultimately worked for me was a combination of clearing targeted cookies AND disabling my VPN. I had no idea that VPNs could cause these kinds of authentication issues with government sites. The most important thing to remember is that your saved tax data won't be lost! I was terrified about losing all my entered information, but it was all still there once I got back in. The IRS stores your form data separately from login credentials. If all else fails, the suggestion about using taxr.ai for troubleshooting browser compatibility issues sounds promising, and several people have had success with Claimyr for getting through to actual IRS support when needed. Don't give up - there's definitely a solution that will work for your specific situation!

I went through this exact same frustrating experience last month! The password field clearing with no error message is maddening - you feel like you're going crazy because there's no indication of what's wrong. Here's what finally worked for me after days of trying everything: I had to completely sign out of my Google account in my browser before attempting to log into Free File. Apparently there was some kind of session conflict between my Google authentication and the IRS system that was causing the silent failure. The steps that worked: 1. Sign out of ALL accounts in your browser (Google, Microsoft, etc.) 2. Clear cookies specifically for irs.gov and any freefile domains 3. Restart your browser completely 4. Go directly to the official Free File site through IRS.gov (not bookmarks or search results) 5. Try logging in with a fresh session It sounds simple but this combination fixed my issue when nothing else would. All my previously entered tax data was still there waiting for me - what a relief! I also learned that the Free File system doesn't play well with certain password managers during the authentication process. If you use one, try typing your password manually instead of auto-filling it. Don't give up! Your data is safe and there's definitely a solution that will work for your specific setup. This thread shows how many different technical factors can cause the same symptom, but also that everyone eventually finds their way back in.

My accountant gave me this rule of thumb: match the expense or income to the year where the activity that generated it happened. For your december work, even though invoiced in january, that goes on 2024 taxes because december is when you did the work.

Just to add another perspective here - I went through this same confusion when I started my consulting business. One thing that helped me understand accrual accounting better was thinking about it this way: you're essentially recognizing the "economic reality" of when transactions happen, not just the paperwork timing. So in your case, the economic reality is that you earned that $4,300 in December 2024 when you completed the work and delivered value to your client. The fact that you didn't get around to invoicing until January doesn't change when you actually earned it. I'd recommend keeping good records of when work was actually completed vs when invoiced vs when paid - it'll make tax time much easier and help if you ever get audited. I use a simple spreadsheet with columns for service date, invoice date, and payment date. Makes it crystal clear which tax year everything belongs to.

Has anyone used H&R Block or TurboTax for these estate returns? I've got a similar situation and wondering if I really need a CPA or if the software can handle it.

I'm going through a very similar situation right now with my grandmother's estate. The quotes I've been getting are all over the place - from $2,800 to $6,500 for what seems like comparable work. One thing I learned is that you should definitely ask about their experience specifically with 645 elections, because not all CPAs are familiar with this option. The CPA I ended up choosing explained that the 645 election can actually save money in the long run because it simplifies the tax reporting by treating the estate and trust as one entity for tax purposes. This means fewer separate returns to file over the administration period. However, you have to make this election on the first 1041 return, so timing is crucial. I'd recommend getting at least 3 quotes and asking each CPA to explain their approach to your specific situation. The cheapest isn't always the best choice, but neither is the most expensive. Look for someone who can clearly explain the process and timeline, and who has handled similar estates recently.

Does anyone know if these rounding rules ever work in our favor? Like is there ever a time when rounding might result in paying less tax? Just curious if there's any strategy to it lol

This is such a great question! I never really thought about the rounding rules until I started doing my own taxes. What really caught my attention in this thread is how the IRS keeps exact cents in their internal systems even though we round on the forms - that's fascinating! I had a similar experience where my manual calculations didn't match what appeared on my tax software's final forms. Now I understand it's because each line gets rounded individually before being used in subsequent calculations. It makes sense from a processing standpoint, but it definitely creates some confusion for those of us who like to double-check the math. The practical impact seems minimal - we're talking about a few dollars difference at most on an entire return. But it's still good to understand why the numbers work the way they do. Thanks everyone for the detailed explanations!

Has anyone actually calculated how big the difference is between filing jointly vs separately with student loans on PSLF? Like actual numbers? My wife and I were in this exact situation and we figured the lower student loan payments would easily outweigh any tax benefits from filing jointly. But after actually calculating everything, we were shocked! Filing separately saved about $280/month on student loan payments ($3,360/year) but cost us around $4,100 in additional taxes and lost credits! We've been losing money for years by filing separately! Do the math carefully with your specific numbers!!

This is such a complex situation that really depends on your specific numbers! I went through something similar last year with my spouse on PSLF and our first baby. A few key things I learned: 1. **Income-driven repayment plan matters**: Since your husband is on IBR, filing separately will indeed keep his payments lower since only his income counts. If he were on REPAYE, spousal income would count regardless. 2. **Child Tax Credit strategy**: The $2,000 Child Tax Credit is huge, but you need to decide who claims your daughter. Generally, whoever has the higher tax rate benefits more from claiming the dependent, but with PSLF you might want to keep your husband's AGI lower. 3. **State tax considerations**: Don't forget to factor in state taxes - some states don't allow separate filing or have different rules. 4. **40 payments left is key**: Your husband is getting close to forgiveness! That's roughly 3.5 years of payments. Calculate the total student loan savings over that entire period, not just one year. My recommendation: Create a spreadsheet comparing total costs (taxes + loan payments) for both scenarios over the next 3-4 years until forgiveness. The math might surprise you either way! Also consider consulting a tax professional who understands PSLF - the intersection of tax strategy and loan forgiveness is tricky, and the stakes are high with your income levels.