IBKR (Pro) sent me only one T5008 which makes sense when I look through it. I did not sell any stock, but I did buy and sell some options last year. However, when SimpleTax attempts to PULL in my T5008 from the CRA, it tries to pull in 12 different T5008s from IBKR! For a third of these, it complains that box #20 is missing. I am curious, is there a way to manually check into the CRA and see exactly what they are showing on THEIR end? I am confused how ONE T5008 ends up in 12 different copies... maybe they split it up or something.
Log into your CRA account. You will find what appears to be a T5008 for each trade. But not all trades are there for some reason. I used the one T5008 from my broker, not the multiple forms in my CRA account .
I tried to find my T5008s being held in my CRA account, but all I could find there are my previous ROEs. After looking at the T5008 that IBKR gave me tonight and thinking it over, I think the mystery is solved. CRA must be breaking each line into an individual file. Matched it to 12 files exactly, and then that makes it more evident why I am getting the Missing Box 20 errors on 8 of them. Looks like my solution here is to manually go line by line on Schedule 3 and enter the trades manually. Let's see how bad I screw THAT up now... This idiot will probably have to return shortly. Haha!
So! I am taxed out tonight, lol. Been going over records all day and I THINK I may be making progress. I just would like some confirmation on something. Let's assume we are just selling options. IIRC, the only thing I should be putting for Cost (Box 20) would be my commissions paid to sell, correct? And for proceeds, I'd put in what I sold them for. I hope this is correct, as I'm starting to lose my own sanity and re-questioning everything tonight. Even so, assuming I am correct in that respect, I've been screwing something up here I think. For my options I bought back to avoid assignment, I've been subtracting what I paid, from what I sold them for, and using just one line for that. Does this make sense, or should I make a new T5008 entry and split the two transactions. I am guessing the latter here. So... part of my sheet I am starting to create: