Thanks for mentioning this! My tax software actually does have an e-file option for superseding returns, but it specifically says to expect a paper check for the refund rather than direct deposit. Do you know if that's always the case or just depends on the timing?

It depends on the timing and how the IRS processes your return. Some people do receive direct deposits for superseding returns, but paper checks are more common because the superseding return often triggers a manual review process. If your software allows e-filing for the superseding return, that's great! It will process faster than paper filing. Just make sure the software properly marks it as superseding (rather than amended) in the electronic submission. Expect your refund to take a bit longer than the standard 21 days - mine took about 5 weeks last year.

Is there any way to check the status of a superseding return? The Where's My Refund tool only seems to recognize my original return.

Are municipal bonds still worth it though? The yield is typically lower than corporate bonds or dividend stocks because of the tax advantage. Wouldn't it make more sense to just keep total income under the standard deduction with higher-yielding investments?

It really depends on your total income needs. If you need more income than the standard deduction would shelter, then municipal bonds become valuable because that portion remains tax-free regardless. For someone who needs, say, $30,000 in annual income, they could take $14,600 from taxable sources (covered by the standard deduction) and the rest from municipal bonds, effectively paying zero federal tax on the full amount. If your income needs are below the standard deduction, then yes, higher-yielding taxable investments make more sense mathematically.

Good point! Some states also tax certain retirement income that's exempt at the federal level. My parents moved from New Jersey to Florida partly because NJ was taxing their pension while Florida has no state income tax.

That's a really good point! Is there an easy way to track all this? Does Fidelity keep those records or should I be maintaining my own spreadsheet?

Fidelity should track the basic purchase info, but in my experience they don't always get the specifics right for tax purposes - especially for older shares. I'd recommend keeping your own records. A simple spreadsheet works great - just note the purchase date, number of shares, what you paid (including any discount), and what the fair market value was on purchase day. Also track the discount percentage your plan offers. Add the sale info when you eventually sell. This saved me tons of headaches at tax time.

The offering date vs purchase date distinction tripped me up! My company has 6-month offering periods, and I sold some shares exactly 1 year after purchase thinking I was good, but it was only 18 months after the offering date. Ended up with a disqualifying disposition without realizing it!

Thank you for that suggestion! I honestly didn't even think about checking with my insurance. Do you know if making a claim would affect my rates for rideshare insurance differently than regular insurance?

It depends on your specific policy, but many rideshare insurance providers understand that minor cosmetic damages are more common in this line of work. I've filed two small claims in the past year and my rates only went up slightly - much less than the cost of paying for the repairs out of pocket. Make sure to ask specifically about their policy for minor cosmetic repairs for rideshare vehicles. Some have special provisions that won't count these types of claims against you as heavily as accident claims.

How much more in deductions did you get with actual expenses vs standard mileage? I drive about 30k miles a year for rideshare in a 2020 Toyota Camry and I'm wondering if I should switch.

Not a stupid question at all! The amounts don't necessarily need to match. The 1099-SA reports the total distributions from your HSA, regardless of how you used the money. If you withdrew more than you spent on qualified medical expenses, you have a few options: 1. If you have other unreimbursed medical expenses from the year, even ones you paid from your regular bank account, you can "retroactively" consider those covered by your HSA distribution 2. You can return the excess distribution to your HSA if you're still within the time limit (usually before tax filing deadline) 3. If neither applies, you'll need to report the difference ($325 in your case) as a non-qualified distribution, which would be subject to income tax plus a 20% penalty

This is good to know! I have contributions coming out of my paycheck - are those considered employer contributions or employee contributions? And should they show on my W2 somewhere?

Contributions made through payroll deduction are considered employee contributions, even though they're taken out before taxes. They should appear on your W-2 in Box 12 with code W. This means they've already been excluded from your taxable wages in Box 1. If your employer makes additional contributions beyond what comes out of your paycheck, those are employer contributions. Both types will be reported on Form 5498-SA which you usually receive in May (after tax filing season), but you don't need to wait for that form to file your taxes.