TaxAct - How to handle 1099B - Multiple positions sold in 2016

[dundee]

Dear Mustacians,

I am doing my taxes with TaxAct (yes, I know, very late this year). I have a brokerage account at Vanguard. I sold several positions last year. For most of my holdings, I was reinvesting the dividends back in the same stock. When I received the 1099B from Vanguard, I got two different tables. One was for the short term gains/losses from the sell of various securities. Another was for long term gains/losses from the sell of the same securities.

When I fill this information in TaxAct, what is the proper way of documenting this?
1. Can I aggregate all short term gains/losses in one 1099B and all long term gains/losses in another 1099B?

or

2. Do I have to have a separate 1099B for each individual security for short and long term? Since I had sold about 8 securities, this would mean total of 16 1099B's.

Thank you for your guidance.

[caracarn]

I believe TaxAct will let you import directly from Vanguard.  It did let me do that with Betterment where I had my accounts until early this year, and if they could pull from them, I can't imagine Vanguard is not supported.  I had over 1,000 entries so I could not even imagine trying to key all that in.

https://www.taxact.com/support/881/2016/how-to-import-stock-information-using-a-csv-file-from-your-broker

https://support.betterment.com/customer/portal/articles/1855089?_ga=1.257893771.1004874033.1462218141 - Might be helpful to see if this will work for you

[dundee]

Thank you for your feedback. I looked into it. Unfortunately, it turns out that TaxAct does not connect directly to Vanguard. And Vanguard does not have tax information available in CSV format.

So, is it necessary to enter each and every security one at a time? Or is it OK to aggregate all the securities in one line?

[MDM]

As long as you separate short term gains vs. long term gains, if the basis for each lot was reported to the IRS then you should be able to summarize the various transactions.  In this situation, the IRS has all the details - filing with the correct totals should suffice.

If some of the long term gains are for lots with basis not reported to the IRS, you might want to list those individually.

[MustacheAndaHalf]

Open TaxAct and look at the "Tools" menu for "Stock Assistant".  That lets you enter 1099-B trades in a spreadsheet format.  You may want to click on the (?) for the category, since that won't make sense without a list of what the categories are and what they mean.  But essentially you'll copy that, and everything else, from the 1099-B.  Much easier than entering each transaction in a Q&A format.

For the past several years I used TaxAct, it did not offer an automatic import of Vanguard data.  TurboTax offers that feature - but for Vanguard you need to do two imports: once for "Vanguard Brokerage" and another import of "Vanguard Mutual Fund Accounts".

[dundee]

Thank you all. I will try to enter the Stock Assistant details this evening. If that doesn't work for me, I will just total them out as they are shown on the Vanguard's 1099B.

[caracarn]

Open TaxAct and look at the "Tools" menu for "Stock Assistant".  That lets you enter 1099-B trades in a spreadsheet format.  You may want to click on the (?) for the category, since that won't make sense without a list of what the categories are and what they mean.  But essentially you'll copy that, and everything else, from the 1099-B.  Much easier than entering each transaction in a Q&A format.

For the past several years I used TaxAct, it did not offer an automatic import of Vanguard data.  TurboTax offers that feature - but for Vanguard you need to do two imports: once for "Vanguard Brokerage" and another import of "Vanguard Mutual Fund Accounts".

So are you saying you CAN import now, just have to use two imports?  I just moved everything to Vanguard again this year, and in the past I used TurboTax, but to save money tried TaxAct this year.  Would like to know if this is possible for next year's taxes.