I have ensured that all settings in TurboTax are correct, including designating the transactions as capital gains and entering the correct disposition dates. However, despite spending 1.5 hours on a call with TurboTax support last night, the issue remains unresolved, and they were unable to provide a solution. Given the cost of the software, I am disappointed that I am unable to access prompt and expert assistance to resolve this technical issue.
HatchS, I had the same issue with the T5008 as you are having. I spent 2 hours on the phone with no resolution. I went back to the T5008 slip and blanked out Box 15 and the "type of income" box, I had Investment and changed it to Capital Gains and the information transferred to the tax return. I hope this helps you out!!
