What about if I have to go through a toll on my way to a client but I wouldn't normally take that route for personal stuff? Like I only use that toll road because it gets me to the client faster?

That's a perfect example of a fully deductible business toll expense. If the toll road is specifically being used to reach a client or for business purposes, then 100% of that toll is deductible. The key test is whether you would have incurred that specific toll charge if you weren't conducting business. This is why good record-keeping is so important. Having your appointment calendar or client meeting logs to match up with the toll receipts creates a clear paper trail showing the business purpose. The IRS loves to see that kind of documentation if they ever question your deductions.

While toll expenses alone probably won't trigger an audit, they could come under scrutiny if your return is audited for other reasons. The IRS typically looks at the whole picture of your business deductions.

I wouldn't recommend this approach. While it might have worked for you, the IRS has gotten much stricter about document alterations. They generally reject hand-modified tax documents now and could potentially flag your return for review, which would delay processing even further.

I tried that but couldn't get through the identity verification - it kept asking for a credit card number that matches my name and address, but my card is pretty new and I've moved recently. Is there another way to verify?

If you can't get through the online verification, you can use the "Get Transcript by Mail" option instead. It takes about 5-10 days to arrive but doesn't require the same strict verification. Alternatively, you can file Form 4506-T and specify that you want the Wage and Income transcripts for your missing years. Another option is to try calling your previous employers' HR departments directly. Many larger companies have systems to provide past employees with W-2 copies, even from several years back. Sometimes this is faster than waiting for the IRS transcripts.

You can also deduct a portion of car maintenance based on business use percentage. I track my total annual miles and what percentage was for rideshare, then deduct that same percentage of oil changes, tire rotations, etc.

That's actually really helpful to know! I never thought about deducting maintenance costs that way. Did you have to provide extra documentation when you filed, or is just keeping your receipts enough in case of an audit?

Can you explain more about this Qualified Business Income deduction? Is that something I can claim as a freelance consultant, or is it only for certain types of businesses?

The Qualified Business Income (QBI) deduction is definitely available to freelance consultants in most cases. It allows you to deduct up to 20% of your qualified business income from your taxable income for federal income tax purposes. There are income limitations that begin to phase out the deduction if your taxable income exceeds $170,050 for single filers or $340,100 for joint filers (for 2025). If your income is below those thresholds, you should qualify for the full deduction regardless of your business type. This can be a huge tax saver - potentially reducing your income tax by thousands.

I switched to an S-Corp two years ago when my net income hit about $80k. It's saved me roughly $4-5k per year in SE taxes. You pay yourself a "reasonable salary" that's subject to FICA (social security/medicare), but the rest can be taken as distributions that aren't hit with SE tax.

Thanks for this advice! Did you end up having to pay any penalties or just return the funds?

I caught mine and corrected it within the same tax year, so I just had to return the funds to my HSA account. No penalties or taxes since I fixed it before filing. Since some of your charges go back to last year, you might have a different situation. If you already filed taxes claiming those as qualified expenses, you'll likely need to file an amended return and potentially pay the 20% penalty on those specific amounts.

This is actually incorrect information. The type of provider (psychiatrist vs therapist) doesn't automatically make the expense qualified. What matters is whether the service is for medical care as defined by the IRS. Mental health treatment IS covered, but general wellness counseling is not considered "medical care" regardless of who provides it.