After 3 hours, i finally got thru to CRA. See responses to my initial questions below:   So what do we do with these T5008 if it is a superficial loss.  I don't want CRA to think I am being neglegent.  In my case, I transferred from non-registered to my TFSA.  How will CRA know?  I don't want to get audited down the line. CRA says you do not have to record your superficial loss on your taxes.  CRA will not automatically know that you had a superficial loss or that it was transferred to a TFSA.  It is up to YOU to keep records to show that you had a loss, and that it was subsequently transferred to a TFSA.  Keep your records with your taxes.  If they have any questions down the line, they will call you and ask for the documentation.     How do i answer these questions: 1.  Did you have investment income that is reported on a slip (i.e. T5, T3, T5008, T5013)?     CRA says indicate "no" 2. Did you buy stocks, bonds, mutual funds, real estate, or other property this year?     CRA says indicate "no" 3.  Did you sell stocks, bonds, mutual funds, real estate, or other property this year?     CRA says indicate "no"   Hope this helps! ... View more

I am in the same situation, however want to claim the Canada Caregiver Amount for Spouse (line 30425) on my return.   I also entered "widowed" under marital status and don't see how I can enter the CC amount.   Not sure how to do this with the PC/Desktop version of TT 2019.   Please advise.   Thanks ... View more

So what do we do with these T5008 if it is a superficial loss.  I don't want CRA to think I am being neglegent.  In my case, I transferred from non-registered to my TFSA.  How will CRA know?  I don't want to get audited down the line.   How do i answer these questions: 1.  Did you have investment income that is reported on a slip (i.e. T5, T3, T5008, T5013)? 2. Did you buy stocks, bonds, mutual funds, real estate, or other property this year? 3.  Did you sell stocks, bonds, mutual funds, real estate, or other property this year?   ... View more

TT automatically assigns the med deduction on my spouses return (lower income).  And same when i run the optimizer.  However, when i take the med deduction, i get a greater return.  Optimize = Greater Return.  To me, this feature is not working properly.  Also, i keep having to re-claim this deduction as TT keeps putting back on to my spouses return.  I say "glitch" needs to be addressed. ... View more