The forgivable loan structure is actually quite different from a direct relocation payment! With your setup, you're correct that the loan itself isn't initially taxable income since it's a debt you owe back. However, each monthly "forgiveness" portion does become taxable income as it's forgiven, which is why it shows up on your paystub gradually. When you leave and have to repay the unforgiven portion, you're essentially just paying back a loan - there shouldn't be any tax deduction for that repayment since you never paid taxes on that money in the first place. This is actually simpler than @0be550eed602's situation where they received taxable income upfront and then have to navigate the repayment complexities. The tricky part with your structure might be if you've already been taxed on some forgiven portions but then leave before the full 24 months. You'd want to confirm with your company whether they'll issue a corrected W-2 to remove the taxable income for portions that weren't actually forgiven due to your early departure, or if you'll need to handle that adjustment on your tax return. Definitely keep documenting everything since the monthly forgiveness creates a more complex paper trail than a lump sum payment!

This is incredibly helpful insight from an HR perspective! I had no idea about the unemployment tax aspect - that's definitely something I wouldn't have thought to ask about. One question about the gross vs. net repayment amount: if they want the gross amount back but I only received the net amount after taxes, am I essentially paying back more than I actually got? That seems like it could create a real financial burden, especially if you're also dealing with moving expenses to the new job. Also, regarding the timing coordination you mentioned - is this something I can actually negotiate with both companies? I'm worried that trying to coordinate departure/start dates around tax implications might look unprofessional or create issues with either employer. How do you typically see people handle this kind of timing request? The multi-state filing requirements are definitely something I need to research more. I hadn't even considered that establishing Colorado residency timing could affect the tax treatment. Do you know if there are any general rules about when you're considered a resident for tax purposes after relocating for work? Thanks for all the practical advice - it's exactly the kind of real-world insight that's hard to find elsewhere!

Yes, if they want the gross amount back, you would be paying more than you actually received - this is unfortunately common and can create a real cash flow problem! For example, if they paid you $13k gross but you only received $10k after taxes, you'd still owe back the full $13k. Some companies will work with you on this (like accepting the net amount or setting up a payment plan), but others stick to the contract terms. Definitely clarify this upfront! Regarding timing coordination - you can absolutely discuss this professionally! Frame it as wanting to ensure a smooth transition for both companies. Something like "I want to make sure I handle all obligations properly with my current employer before starting" sounds much better than "I'm trying to optimize my tax situation." Most HR departments understand these logistics. For state residency, it typically depends on where you're physically present and where your "domicile" is, but the rules vary by state. Generally, you become a resident when you move there with intent to stay permanently. Colorado considers you a resident starting from your move date, while Oregon will consider you a resident until you leave. You'll likely file part-year returns in both states covering the portions of the year you lived in each. The key is planning ahead and getting everything documented!

This is really helpful info! I didn't know about Form 8379 - that might actually apply to my situation since I'm married and my spouse had some old debt issues. Definitely going to check my online account first before calling again. Thanks for the detailed advice! 🙏

Great advice about calling early! I'm definitely going to try the 7am thing tomorrow. Quick question though - when you say "refund department" do you literally ask for that by name or is there a specific extension/menu option? I always get lost in their phone tree system 😅

This is incredibly helpful! I'm just starting to deal with my non-resident alien filing and the manual calculation part seems daunting. When you say you used a spreadsheet to track adjustments - did you basically recreate all the tax calculations that Sprintax did, or just the parts affected by the HSA deduction? Also, the point about losing e-file capability is something I hadn't considered. Do you know if there's any way to still get faster processing, or does mailing it in mean waiting the full 6-8 weeks for any refund?

@Ava Kim For the spreadsheet tracking, I didn t'recreate all of Sprintax s'calculations - just the key ones affected by adding the HSA deduction. Specifically, I tracked the AGI adjustment subtracting (the HSA contribution ,)then recalculated the standard deduction application, taxable income, and final tax liability. The math is pretty straightforward once you have the HSA amount from Form 8889. Unfortunately, mailing does mean slower processing. Paper returns typically take 6-8 weeks minimum, sometimes longer during busy season. There s'no way around this when you have to attach manual forms that the e-file system can t'handle. The trade-off is getting your deductions properly claimed versus faster processing. One small tip - if you re'expecting a refund, make sure to double-check your bank account information on the return since direct deposit can still work even with paper filing, which speeds up the refund portion once they process it.

This is really helpful timing advice! I'm actually in the middle of this exact situation right now. One question about the HSA contribution timing - if I made contributions through payroll deduction throughout 2024 but also made some additional direct contributions in early 2025 (before April 15), do I need to wait for those direct contributions to fully process before filing? My bank shows them as pending but not yet posted to the HSA account. I'm worried about claiming a deduction for contributions that might not technically be "made" yet according to IRS rules, especially since I'm already doing the manual Form 8889 process. Also, regarding the earned income limit for IRA contributions - does this include only salary/wages, or would it also include things like bonuses or stock compensation that show up on my W-2? My situation is a bit more complex since I have both regular salary and some equity compensation.

The IRS doesn't explicitly state a preference as long as all wash sales are properly identified and reported. But in practice, most major brokerages (Schwab, Fidelity, etc.) now report wash sales by adjusting the cost basis of replacement shares, which is the TradeLog approach you mentioned.

This is really helpful context! As someone new to dealing with wash sales, I'm curious - when you say "exit the position completely," does that mean I need to wait until I've sold all shares of that security before the wash sale calculations are finalized? I have some positions where I've been buying and selling the same stock multiple times throughout the year, so I'm not sure when the "wash sale chain" actually ends.

Great question! The "wash sale chain" can get really complex when you're actively trading the same security. You don't necessarily need to exit the entire position - it's more about tracking each specific lot of shares and their associated wash sale adjustments. For example, if you buy 100 shares, sell at a loss (wash sale), then buy 100 replacement shares, the disallowed loss gets added to the cost basis of those replacement shares. When you eventually sell those replacement shares, that's when the wash sale "resolves" for that particular chain - regardless of whether you still hold other shares of the same stock. The tricky part is when you have overlapping wash sale periods with multiple buys and sells. Most good tax software will track these individual chains automatically, but if you're doing it manually, you'll want to use FIFO (First In, First Out) or specific lot identification to keep track of which shares are tied to which wash sale adjustments. This is actually another reason why the software discrepancies you're seeing happen - different programs may use slightly different methods for matching up wash sale chains when you have complex trading patterns.

This is such helpful advice! I'm actually in a similar boat - just started gig work this year while my partner has been doing it for a while. The point about factoring in W-2 withholding is something I hadn't really considered. Do you have any rough guidelines for how to calculate that? Like if my regular job withholds $X per year, how do I figure out how much that reduces my quarterly estimated payments? Also, those quarterly deadlines you mentioned - are those the same for every state or do some states have different due dates? I'm in California and want to make sure I'm not missing anything on the state side.

Great question about calculating the W-2 withholding impact! Here's a simple way to think about it: look at your spouse's most recent paystub and multiply the federal tax withheld per pay period by the number of pay periods in the year. That gives you the annual withholding amount that's already going toward your joint tax liability. For example, if $400 is withheld from each biweekly paycheck, that's $400 × 26 = $10,400 per year in withholding that reduces what you need to pay in estimated taxes. As for California, the state quarterly due dates are the same as federal (Jan 15, Apr 15, Jun 15, Sep 15), but California has its own estimated tax requirements that might be different from your federal calculation. You'll want to use Form 540ES for California estimated payments. The good news is most tax software or tools like the ones mentioned above can handle both federal and state calculations together. The key is to calculate your total expected tax liability (federal + state + self-employment tax), subtract what's already being withheld from W-2 jobs, and then divide the remainder by 4 for your quarterly payments.

This is really helpful! I'm new to self-employment taxes and wondering - when you mention the 15.3% self-employment tax, is that in addition to regular income tax rates? So if I'm in the 22% tax bracket, would I be looking at roughly 37.3% total on my gig income? That seems really high but want to make sure I'm calculating this correctly for our quarterly payments.