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I receive an entitlement to company shareas as part of my annual incentives - they vest over 2 years (50% per year) and I need to excercise my right to these shares within 7 years. I had accumulated shares over about 4 years and made a decision to execrcise my rights when the shares were valued at around $8 per share. I had intended to then sell a portion of the shares to cover my tax liability which arose when I declared those shares as "income", however I am subject to restricted trading windows. Not long after the shares were allocated to me, COVID hit, and my shares halved in value by the time I was able to sell them in a trading window. I find myself left with a tax debt of around $30K (based on the value of the shares when they were actually awarded to me) and this is around about their entire current value.
Do I have any grounds to appeal the tax debt? I never actually earned the "income", it was all on the paper value of the shares, which I couldn't sell due to trading restrictions. It seems really unfair that the tax office is basically getting the full value of my "incentive". Clearly not well managed on my part but COVID could not ahve been foreseen and I feel really unfairly disadvantaged -- If I sell them at the lower price to clear my debt, can I claim the loss from my next years income?
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