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

[a_big_dumb_animal]

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!

[RobertB4444]

You can enter your summary totals for each section of the 1099-B instead of typing in each individual transaction.  This is a lot less work.  If, after entering your summary totals, the system determines that you are required to send your 1099-B to the IRS then it will let you know the steps to do so.  

@a_big_dumb_animal 

[a_big_dumb_animal]

Thanks @RobertB4444 

I tried that, but it wants the Date Acquired (Box 1B).

[GeorgeM777]

To finish your return regarding your ESPP transactions, you need the information requested by TurboTax.  One option you might consider at this point is to research your former employer's Form 10-Q (quarterly report) or Form 10-K (annual report) in order to ascertain your employer's offering period and eligible purchase dates.  In other words, you are working your way backwards to find out when during your employment period--February 2021 - April 2022--you would have purchased your ESPP shares.  If you can ascertain a reasonable purchase date, then you can use Yahoo Finance or any other stock application to get an idea of the stock price on your date of purchase.

As an example of what a Form 10-Q might provide, below is information from a public company's recent Form 10-Q that describes the company's ESPP.  As you review the below information, you will see that the company's ESPP has an offering period, and then it also provides for specific dates on which purchases can be made.   

Offering Dates.

 (a) Offering Periods shall be of six (6) months duration, with one such Offering Period commencing on each September 16 and ending on the following March 15, and another commencing on each March 16 and ending on the following September 15.  

Each such Offering Period shall consist of two (2) Purchase Periods, each of which shall be of three (3) months duration. The Offering Period commencing on September 16 shall have Purchase Periods commencing on September 16 and December 16 and ending on the following December 15 and March 15, respectively.

The Offering Period commencing on March 16 shall have Purchase Periods commencing on March 16 and June 16 and ending on the following June 15, and September 15, respectively. The first day of an Offering Period is the “Offering Date” for that Offering Period. 

To find your former company's Form 10-Q enter your former employer's name in a Google search bar and include the phrase "Form 10-Q." (you can omit the quotation marks).  Search for the Form 10-Q that covers the period of your employment.  Then select the most relevant search item and retrieve the document.  You can search the document using the search term "employee purchase" by selecting Ctrl  F on your keyboard (Windows) or Command  F on your keyboard (Mac).  

Let us know if you need additional guidance.  If you prefer, provide the name of your former employer and we can attempt to further research this matter.

@a_big_dumb_animal