16 Has anyone actually calculated what the tax might be for the OP? If you bought at around $15K and sold at $27K, that's a $12K gain. Half of that ($6K) is taxable and gets added to your income. If you're in Ontario and make around $60K otherwise, that $6K would be taxed at roughly 30%, so you'd owe about $1,800 in additional tax. Of course, this varies by province and income level.

Just want to add something that might help - make sure you keep all your documentation! You'll need your original purchase statements from Starbucks showing when you bought the shares and at what prices. Also keep the sale confirmation showing the $27K proceeds. The CRA might ask for these documents if they review your return, and having everything organized will make filing much easier. If you've lost any paperwork, contact Starbucks HR or whoever manages the employee stock plan - they should be able to provide statements showing your purchase history. Also, depending on how long you held the shares, you might want to double-check that this qualifies as a capital gain and not employment income. Generally employee stock purchases are treated as capital gains when sold, but there can be exceptions depending on the specific plan structure.

Has anyone used the IRS Tax Withholding Estimator online? I tried it but got totally confused when entering multiple jobs.

I've been in a similar situation with multiple variable income jobs, and here's what worked for me after a lot of trial and error: Since you can't predict the variable income accurately, I'd recommend using a "safe harbor" approach. Calculate 110% of last year's total tax liability and divide that by the number of pay periods from your full-time job. Have that amount withheld as additional withholding on line 4(c) of your W-4 for your steady job. This way, even if your variable jobs earn more than expected, you'll avoid underpayment penalties because you're meeting the safe harbor rule. You might get a refund, but that's better than owing plus penalties. For the variable jobs, I keep their W-4s simple - just basic information in Steps 1 and 5, no additional withholding. Let your main job do the heavy lifting on withholding. Also, consider making quarterly estimated tax payments if your variable income is substantial. You can adjust these throughout the year as you get a better sense of your actual earnings. The IRS Form 1040-ES has worksheets that help with this approach. The key is building in a buffer for uncertainty rather than trying to be perfectly precise with unpredictable income streams.

Pro tip: The system is usually most stable between 2-4pm EST. Thats when I always check mine with no issues

I've been having the same issue since around 7am this morning! Keep getting that "transcripts unavailable" error message. Really frustrating when you're trying to track your refund status. Hopefully it's back up soon - this seems to happen way too often during tax season.

Has anyone tried accessing through the IRS2Go mobile app instead of the website? Is that working any better today? • Sometimes the mobile interface uses different server resources • Wondering if the API endpoints have different availability • Trying to determine if this is a full system outage or just web portal Really need my transcript for a loan application due this week.

I'm experiencing the exact same issue! Been trying since 7 AM this morning and keep getting timeout errors. What's particularly frustrating is that I called the IRS helpline and after a 45-minute hold, the representative told me they're aware of "technical difficulties" but couldn't give me a timeline for when it'll be fixed. She suggested trying again in 24-48 hours, which is useless when I have a CPA appointment tomorrow and need these transcripts beforehand. The system seems to fail right at the identity verification step - I can log in but can't actually retrieve any documents.

This happened to me last week. Filed 2/20, transcript updated 3/1 showing deposit date of 2/28. Got my money on 3/4. Don't worry - the money is coming. The system is just overloaded and the dates get messed up. Your return is approved and that's what matters!

Katherine, I completely understand your frustration! That "time travel" feeling with tax dates is something many of us have experienced. From what I've seen in similar situations, when your transcript shows a deposit date that's already passed but just updated today, it usually means your refund was approved and is now in the disbursement queue. The 2/22 date is likely when the system initially processed your refund, but due to high volume this time of year, there was a delay in actually sending it out. I'd expect to see the money in your account within the next 3-5 business days. Keep checking your bank account (I know it's hard not to!), and if nothing shows up by early next week, then it might be worth calling the IRS. Hang in there - your money is on its way!