As someone who's been through this exact situation, I want to add that you should also check your bank records if you made any payments along with your return. If you paid estimated taxes or owed a balance and made an electronic payment around the same time you mailed your return, that payment date can serve as additional evidence of your intent to file timely. The IRS systems often correlate electronic payments with paper returns, and having both the Priority Mail tracking showing delivery AND a contemporaneous electronic payment can strengthen your case if questions ever arise. I had a situation where my Priority Mail tracking wasn't initially accepted by an IRS representative, but when I mentioned the electronic payment I made the same day I mailed the return, they were able to locate my return in their system and confirm everything was properly filed. Also, don't forget to check the "Where's My Refund" tool or create an account on IRS.gov to monitor your return status. Once it shows up as "received" in their system, you'll have additional confirmation that your Priority Mail delivery was successful and your return is being processed normally.

I completely understand your anxiety about this situation - it's one of those moments where you second-guess every decision after the fact. The good news is that Priority Mail tracking does provide legitimate proof of mailing and delivery that the IRS will generally accept, even though it's not as legally robust as Certified Mail. Your Priority Mail service includes tracking that shows when the package entered the postal system and when it was delivered to the IRS processing facility. This creates a documented timeline that demonstrates you filed by the deadline. While the postal clerk was somewhat correct that both services provide tracking, they understated the legal differences - Certified Mail offers stronger proof with its return receipt, but Priority Mail tracking is still valid evidence. Here's what you should do immediately: Save your Priority Mail receipt and take screenshots of the complete tracking history showing delivery confirmation. This data expires from the USPS website after about 120 days, so don't delay. Print everything and save digital copies as backup documentation. The reality is that millions of tax returns are successfully sent via Priority Mail every year without issues. Your tracking confirmation showing timely delivery to the IRS facility should protect you if questions ever arise about meeting the filing deadline. Try not to stress too much - you took reasonable steps to file on time, and the documentation will support that if needed.

Adding to the excellent points already made - one aspect that's often overlooked is the interaction between state and federal tax treatment of bonus depreciation. While you're focused on offsetting federal short-term capital gains, some states either don't conform to federal bonus depreciation rules or have different conformity dates. If you're in a state like California or New York that has historically decoupled from federal bonus depreciation, you might end up with significant book-tax differences that create ongoing compliance complexity. This could affect your overall tax strategy, especially if you're planning to take substantial first-year depreciation. Also, since you mentioned this is a SaaS business, consider whether any of the software qualifies as "internal use software" under Section 167. The depreciation periods and methods can differ from purchased software, and if the target company developed some software for internal operations versus customer-facing applications, you might need to separate these for different depreciation treatment. Given the tight timeline you're working with and the complexity of coordinating federal/state issues with business acquisition structuring, I'd suggest running scenarios with your tax advisor that model the multi-year impact, not just the first-year benefit. Sometimes a more measured depreciation approach provides better overall tax efficiency.

I'm dealing with a similar situation and wanted to share something that might help with your timeline concerns. When I was rushing to complete an acquisition for tax purposes, I learned that you can actually use Section 1031 like-kind exchanges in combination with bonus depreciation strategies, but only in very specific circumstances. The key insight for SaaS acquisitions is that you need to be extremely careful about the "active business" requirement you mentioned. The IRS has been scrutinizing cases where taxpayers acquire businesses primarily for tax benefits rather than legitimate business purposes. Make sure you have solid documentation showing business reasons for the timing - market opportunities, competitive positioning, etc. One thing that saved me was structuring the deal with an earnout provision tied to business performance metrics. This helped demonstrate that my primary motivation was business growth rather than tax avoidance, while still allowing me to claim the depreciation benefits in year one on the portion of the purchase price paid at closing. Also consider whether you can elect out of bonus depreciation on certain assets if it creates better long-term tax efficiency. You're not required to take maximum depreciation if a more strategic approach better serves your overall tax situation across multiple years.

I'm experiencing the exact same delays! Filed my Maryland return on February 14th and it's been stuck in "being processed" for over 5 weeks now. This is my 8th year filing in MD and I've never seen anything like this - usually get my state refund within 6-10 days. I finally got through to the comptroller's office after multiple attempts and they confirmed it's purely a processing backlog issue, not a problem with my return. The agent said they've had to completely overhaul their fraud detection systems this year which is causing these massive delays for everyone. She mentioned they're working overtime to clear the backlog but couldn't give me a specific date. It's really frustrating because I've been putting off some important car repairs waiting for this refund. Reading everyone's comments here is actually really reassuring though - I was starting to panic that my return got flagged for audit or something worse. Hang in there Grace, sounds like we're all dealing with the same systemic issues with Maryland's processing this year!

I'm dealing with the exact same frustrating situation! Filed my Maryland return on February 12th and it's been stuck on "being processed" for over 6 weeks now. This is my 4th year filing in MD and I've never experienced delays even close to this - typically got my state refund in 5-8 days max. I called the comptroller's office three times over the past two weeks and each time they gave me the same story about enhanced fraud detection systems causing unprecedented backlogs. The last agent I spoke with said they're working through returns filed in mid-February now, so hopefully that means movement soon for those of us who filed around that time. It's incredibly frustrating because like you, I have medical expenses I've been postponing - specifically some dental work that really can't wait much longer. Reading all these comments is actually really reassuring though, as it confirms this is a statewide processing crisis and not an issue with our individual returns. Really hoping Maryland figures out how to streamline their new systems because this level of delay is unacceptable for people who depend on their refunds for essential expenses!

I went through this exact scenario two years ago and made some costly mistakes initially. The key thing to understand is that Box 12V represents the "bargain element" - the difference between what you paid for the options and the fair market value when you exercised them. This is always ordinary income, not capital gains. Here's what I learned the hard way: When you sell the actual shares later, your cost basis is the exercise price you paid PLUS the Box 12V amount that was already taxed as income. This prevents double taxation on that portion. Only any additional appreciation (or loss) from the exercise date to sale date becomes capital gain/loss that can be offset with other investment losses. So to answer your original question - no, you can't back out the Box 12V from Box 1, and you can't use capital losses against it. But you can use those losses against any capital gains from the actual stock sale if there was additional appreciation after exercise.

I've been dealing with stock compensation for several years now and want to emphasize something important that might help with your planning. While you're correct that you can't offset the Box 12V ordinary income with capital losses, you should look at the timing of when you exercise options versus when you sell shares. If you have significant capital losses from other investments, consider holding onto the shares you received from exercising your NQSOs for a while before selling (assuming you can afford to). This way, if the shares appreciate further, you'll have capital gains from the stock sale that CAN be offset by your existing capital losses. Also, make sure you're keeping detailed records of your exercise date, exercise price, and the fair market value on exercise date (which should match your Box 12V amount). You'll need all this information to correctly calculate your basis when you do sell the shares. I learned this the hard way when I couldn't find my old records and had to reconstruct everything during tax season. The tax treatment of stock compensation is definitely one of those areas where getting professional help early can save you money and headaches down the road.

Has anyone checked line 30 on Form 1040 (Recovery Rebate Credit) on both returns? That was the source of discrepancy for me last year - one software automatically calculated it correctly while the other one needed manual input.

I just went through this exact same situation last month! Had a $89 difference between TurboTax and FreeTaxUSA. After comparing both returns line by line, I discovered the issue was in how they handled my dependent care FSA contributions on Form 2441. TurboTax was correctly reducing my eligible dependent care expenses by the FSA amount I contributed, while FreeTaxUSA was double-counting it somehow. The IRS instructions are pretty clear that you can't claim the dependent care credit for expenses you already paid for with pre-tax FSA dollars. My advice would be to print out both completed returns and go through them systematically: - Compare your Form 1040 line by line - Check any schedules you have (A, B, C, etc.) - Look at state return calculations if applicable - Pay special attention to credits like Child Tax Credit, Education Credits, and Dependent Care Credit The $64 difference you're seeing is definitely worth investigating. In my case, TurboTax had it right and I would have gotten in trouble with the IRS if I'd filed the incorrect return showing the higher refund.