I've been dealing with this exact issue for months! One client has been dragging their feet on payments, claiming they need me to use their "secure portal" for tax documents. After reading through these responses, I'm realizing they might just be using this as a delay tactic. The security concern is real though - I've seen too many data breaches from third-party systems. What I'm planning to do now is send them my standard W-9 via certified mail with a polite cover letter explaining that this meets all IRS requirements for taxpayer identification. If they still refuse, at least I'll have documentation that I provided the required information in an acceptable format. Has anyone tried the certified mail approach? I'm hoping having that paper trail might encourage them to stop dragging this out.

I've been following this thread as someone who's dealt with similar W-9 issues, and there's one angle that hasn't been mentioned yet - what to do if you're stuck in a situation where the company genuinely has technical limitations. I had a client whose accounting system literally couldn't process manual W-9 entries (they'd switched to a fully automated vendor management platform). In that case, I asked them to provide me with their data security certification and privacy policy before using their portal. They were able to show me they were SOC 2 compliant and used bank-level encryption. The key was getting them to put in writing that they would delete my information from their system after the required retention period and that they wouldn't use it for any purpose other than tax reporting. Once I had that email commitment, I felt comfortable using their system. So if you do end up needing to use a company's portal, don't be afraid to ask for security documentation and written commitments about data handling. Any reputable company should be willing to provide this information.

Heads up - don't forget state tax implications too! My S-Corp has owners in 3 different states and each state has different rules about estimated payments. Some require the S-Corp to make composite payments on behalf of non-resident shareholders, while others require each shareholder to file their own estimated payments. This created a huge mess for us at tax time last year because we didn't plan properly. Had to pay penalties in two states.

One thing that hasn't been mentioned yet is the importance of establishing clear procedures early in the year for tracking each owner's quarterly payments. We learned this lesson the hard way when tax season came around and nobody could remember who had paid what. I'd recommend creating a shared spreadsheet or using accounting software to track each partner's quarterly payments throughout the year. Include columns for each owner's projected annual tax liability, quarterly payment amounts, actual payment dates, and any adjustments made based on updated income projections. Also, make sure your S-Corp provides regular profit updates to all owners (at least quarterly, preferably monthly if income is volatile). This allows each owner to adjust their estimated payments if the business is performing significantly better or worse than projected. The last thing you want is for someone to underpay all year because they were working off stale projections. Consider having a brief quarterly meeting where you review actual vs. projected income and discuss any needed adjustments to individual estimated payments. It takes maybe 30 minutes but can save everyone from penalties and surprises at tax time.

I'm in a very similar situation right now - collecting donations through my Zelle account for a coworker whose family was in a car accident. Reading through all these responses has been incredibly helpful, especially the specific advice about Form 8275 and the documentation requirements. One thing I want to add from my research: make sure you transfer the funds as quickly as possible after receiving them. The IRS looks at how long money stayed in your account when determining whether you had "control" over it. The faster you move it to the intended recipient, the stronger your case that you were just a conduit. Also, for anyone dealing with this situation, consider setting up the official fundraiser (GoFundMe, etc.) BEFORE you start collecting donations if possible. It's much cleaner from a tax perspective if people donate directly to the platform rather than going through your personal accounts first. @Nick - definitely keep every screenshot, text message, and email that shows the donations were intended for your sister, not you. The IRS will want to see evidence of intent if they ever question this.

This thread has been incredibly helpful! I'm dealing with something similar where I collected about $8,500 through my personal Venmo for a neighbor's house fire, then transferred it all to their official fundraiser. One thing I want to emphasize that I learned from my accountant: keep a detailed spreadsheet showing EVERY transaction with dates, amounts, donor names (if available), and transfer details. The IRS wants to see a clear money trail that proves you never commingled these funds with your personal money or used them for anything else. Also, when you transfer the money to GoFundMe, make sure to do it in chunks that match your Venmo deposits as closely as possible. Don't just transfer one lump sum - it makes the paper trail harder to follow. I transferred mine in 3-4 batches over a few days, keeping screenshots of each transfer. @Nick - since you mentioned you kept detailed records, make sure those records include the PURPOSE of each donation if donors mentioned it in their Venmo messages. Having evidence that people explicitly stated the money was "for your sister's family" or "for the fire victims" really strengthens your case that this was never intended as income to you personally.

Don't forget about education credits too! Since he's in college and you're claiming him as a dependent, YOU would be the one eligible to claim any education credits for his expenses (like the American Opportunity Credit) on your return, not him. Could be worth up to $2,500 if he has qualified education expenses.

Based on what you've described, you should definitely be able to claim your brother as a dependent! Since he's 19 and a full-time college student, he can qualify as a "qualifying child" rather than just a "qualifying relative" - which is actually better for you because there's no gross income limit for qualifying children under 24 who are students. The key tests you need to meet are: 1. Relationship - ✓ (he's your brother) 2. Age - ✓ (under 24 and full-time student) 3. Residency - ✓ (lived with you more than half the year since February) 4. Support - ✓ (sounds like you're covering all his major expenses) His $9k income won't disqualify him since he's a student under 24. Just make sure when he files his own return that he checks the box indicating someone else can claim him as a dependent. And definitely keep good records of all the support you're providing - rent, utilities, food, etc. - in case you ever need to prove you're covering more than half his total support for the year. You're being really generous helping him get started in life!

One thing to remember is that even with zero income/expenses, if your foundation has assets (like money in a bank account), you'll still need to report those on the balance sheet section of the 990-PF. Many first-time filers get hung up on the income portions being zero but forget about reporting the assets. Also, don't forget the minimum distribution requirements for private foundations! Even if you had no income this year, you might still be required to distribute 5% of your investment assets. If you truly have zero assets and zero income, that's different, but make sure you're clear on which situation applies to you.

As someone who's dealt with this exact situation, I completely understand your frustration! The key issue you're running into is that the 990-PF has mandatory sections that must be completed even with zero activity - you can't just leave them blank. For TurboTax Nonprofit, try entering "$0" explicitly in those flagged fields instead of leaving them empty. The software often interprets blank fields as incomplete rather than zero. Also, make sure you're filling out Part VIII (Information About Officers, Directors, etc.) completely - this section is required regardless of financial activity. That said, if you continue having issues with TurboTax, you might want to consider switching to software specifically designed for 990-PF forms. The general tax software packages sometimes struggle with the unique requirements of private foundation returns, especially for inactive organizations. One last tip - double-check that you actually need to file a 990-PF and not a 990-EZ or 990-N. The filing requirements depend on your foundation's gross receipts and total assets, not just current year activity. If you qualify for a simpler form, that might solve your headache entirely!