Will my Form 5498 arrive in time for 2025 filing deadline?

Oh thank goodness! So I don't need to wait for Form 5498 to file my taxes? The customer service rep made it sound like I'd be in trouble if I filed without it. Just to clarify - even though this was about $37,500 moving from one traditional IRA to another, I don't need to report this transaction anywhere on my return?

You're absolutely correct - you don't need to wait for Form 5498 to file your taxes. A direct trustee-to-trustee transfer between traditional IRAs is not reportable on your tax return because it's not a taxable event. The $37,500 amount doesn't matter in this case since you're not taking a distribution - you're just moving money from one IRA custodian to another. The Form 5498 is primarily for the IRS's information and record-keeping purposes, and the May timing is specifically designed to accommodate contributions made up until the tax filing deadline.

How accurate is this tool? I'm in a similar situation but I also converted some traditional IRA funds to Roth last year, so my situation is a bit more complicated. Does it handle Roth conversions too?

Does this tool actually connect to the IRS systems somehow? Seems a bit sketchy to upload financial docs to a random website someone mentioned on reddit...no offense.

The tool is extremely accurate - it uses the same tax rules and regulations that professional tax preparers use, just in a more accessible format. Yes, it absolutely handles Roth conversions, which is actually a more complex situation than yours because those are reportable transactions. It doesn't connect directly to IRS systems - it's an analysis tool that works locally with your documents. All uploads are encrypted and secure, and they don't store your actual documents after analysis. I was skeptical too at first, but their privacy policy is really solid and they explain exactly how your information is protected.

Wait, how does this even work? Are they somehow jumping the queue for IRS phone lines? That doesn't seem legit.

Yeah right... nobody gets through to the IRS in 20 minutes. I spent 3 hours on hold last month just to ask a basic question about my stimulus payment. Is this some kind of paid service or something?

It uses a callback system that navigates the IRS phone tree automatically. When your turn comes up, it calls you and connects you directly to the agent. It's completely legitimate - they're just using technology to handle the waiting part so you don't have to sit on hold yourself. Yes, it is a paid service, but considering I spent 4 hours on hold previously trying to get through and eventually gave up, the time saved was absolutely worth it. They don't actually "jump the queue" - you still wait your turn, but their system does the waiting instead of you sitting there with your phone on speaker for hours.

It was definitely a direct transfer where I never received any funds personally - I just authorized the new bank to pull the funds from my old IRA. So sounds like I won't get a 1099-R either. But hypothetically, if someone DID receive a check and then deposited it in the new IRA within 60 days, how would they report that? Just curious for future reference.

In a direct transfer where you never received the funds, you're correct that you won't receive a 1099-R, and there's nothing to report on your tax return. If someone did receive a distribution check and then completed a 60-day rollover, they would receive a 1099-R from the first institution with distribution code G. They would need to report this on their tax return (generally on lines 4a and 4b of Form 1040), showing the full amount on line 4a but putting $0 on line 4b (since it's not taxable if properly rolled over). They would write "Rollover" next to line 4b to indicate why the taxable amount is zero. This ensures the IRS knows you received funds but properly rolled them over within the allowed timeframe.

This is so helpful, thank you! So just to confirm - when my tax software asks if I made any "contributions" to my traditional IRA this year, I should NOT count the rollover amount as a contribution, right?