1099-B / T4PS | Capital Loss, How to Properly File?

Hey all,

 

I've had a couple fragmented posted thus far on this topic, and now I think I'm finally at a point of ... clarity'ish. 

 

At this point, I'm assuming I need to pay a tax advisor, just hoping someone can save me here before I make the investment!

 

Background:

- Worked for a company in the USA, that has a Canadian Parent

- Purchased employee stocks via ESPP program for the duration of my tenure (Feb '21 to Apr '22)

- Sold my shares in May '22

 

Tax info:

- No longer have access to login to Shareworks (Morgan Stanley)

- Recieved a PDF of all itemized transactions (4 pages long) showing each individual buy

- Recieved a T4PS, showing a capital loss

- Recieved a 1099b, missing Date Acquired and Cost or Other Basis

- The 1099b shows two seperate line items - one for employee and one for employer contributions

- Employer at $5k for proceeds, Employee at $10k for proceeds (rounded for ease of dialogue)

- The 1099b does not state the "Sales Section"; however, it does state "Proceeds from broker and barter exchange trnsactions noncovered securities with undetermined holding period" --- assuming this equates to "Unknown term basis not reported to IRS" on TT?

 

How to manage on TurboTax?

- TT is asking for Date Acquired and Cost or Other Basis - I lack these

- Is in fact "Unknown term basis not reported to IRS" the proper sales section option?

- My question is more so ... do I really need to manually enter, every single transaction over the past year? I can't imagine this being viable for someone who has had a longer tenure with a company. Are they really expecting us to manage every single ESPP purchase?

- I'm assuming this is what the "adjust cost basis" is meant to be - an average of the overall sales?

- The above is what I've tried, but when selecting either blank, or various for the date (1b), it flags the $5k transaction as needs reviewed, but yet it doesn't flag the $10k transaction?

 

Happy to share more details. I'm still playing trying to see If I can fat finger my way through this, but I'm obviously nervous about screwing it up.

 

Any/all insight is most appreciated!

 

Thanks!