1099-B says short-term or long-term determination is unknown to Broker. I must determine short-term or long term based on my records.

[PETALS714]

Choices are Part I with Box B checked or Part II with Box E checked

[fanfare]

If all your purchases were LT, i.e. you stopped investing over a year ago. enter one transaction for the total number of shares, the DateAcquired is "Various", which you will find is a valid "date". Your transaction category is Box E.

[PETALS714]

I agree with everything you're saying. One more question, I don't have records of when we started making monthly contributions to the  fund, so having trouble coming up with a cost or basis. For some reason, there's an amount in the cost or basis box for all the transactions but the last one.

[fanfare]

It would be odd they have the basis but not the date.
in any case, if you are missing just one basis, use the same cost per share you got on the transaction previous. It's not going to make much difference one way or another.

[ThomasM]

Since you already know the sale date(s) of the securities, it's the acquisition date(s) which will dictate whether they're S/T or L/T.  S/T means you held it one year or less; L/T means you held it greater than one year.

If you bought the stock so long ago that you can't remember, then it's L/T, and you'll choose Part II box E.  If you're not sure what you paid for it, try to think back and arrive at a reasonable estimate of the date of acquisition, and then check the historical stock price on that date to arrive at your "cost basis."

If you inherited the stock, then it's L/T (likewise, Part II box E).  You'll write "inherited" for "date of acquisition."

If these securities were inherited, then you will receive what's called a "stepped up" basis, meaning your cost will be the value of the stock on the person's date of death.

[PETALS714]

Thank you! Pretty confident it's L/T because we haven't contributed to the fund in years. We set it up over 10 years ago, but we contributed small amounts each month for years. I don't have complete paper records. I can't access online because we started with one company and it was bought out by another company. What's your suggestion if it isn't just one acquisition date, but many transactions, monthly over several years.

[ThomasM]

One way might be to split the total annual purchases into 2 lots per year (June 30 & Dec 31), and do that for each year you were investing.  Then check the historical prices for those two dates each year.  Or if you're more comfortable using quarter years, you could do that.  The idea is to have a reasonable method of estimation, and then apply it consistently over all the years.