I received 1099B for 2017 from Prosper with several debt sale (no cost basis)and charge-offs . Do I report each entry separately or can I report all as summary?

[sum1-makish]

Debt sale entries do not have cost basis. How would I calculate cost basis?

[KittyM]

You will need to report each sale separately or  (if you choose to enter summary entries) you will have to send a copy of your 1099-B to the IRS.  TurboTax will print an 8453 for you if this is your choice, and you will attach the copy and mail it.  If there are only 10-20 entries, I find it easier to enter them manually.

"Cost Basis" is what you paid for your investment.  This information should be on the statement for the period in which you purchased the investment.

[cartercoe]

This is such a hassle.  Had I known how difficult it is to report Prosper investments to the IRS, I would have never invested with them.  Pain in the rear and all for measly returns.

[Anonymous]

Agreed, what a terrible hassle.

[silex840]

Such is life argh!!

[nabil-boutaleb]

+1. This is a terrible waste of time.

[gs_garcia]

Everyone continue to email Prosper about this so that changes will be implemented for next year

[gs_garcia]

Actually, there's a workaround to entering manually! You only need to mail in the substitute 1099-B statement provided by Prosper—along with Form 8453. The substitute statement contains all of the transactions that need to be reported in an IRS-sanctioned format (it meets the IRS requirements for a 1099-B substitute form).

I just found out about this and I'm so glad I don't have to enter 20+ pages of transactions...

[Anonymous]

True, but they don't sum up the totals for short and long term cost-basis separately, only the all-together total which you can't report to the IRS. I had to email them after adding up all the many pages of entries (tabula helps), and they did eventually send me the totals. Printing and mailing a 20 page 1099-B/8453 is an inconvenience vs. the auto-importing of lending club - still better than manual entry I suppose.

[gs_garcia]

Agh yeah I see your point. Prosper really needs to implement auto-import.

[silex840]

Seriously Prosper! Implement this already!

[mthomas4]

I created a tool to convert Prosper 1099-B transactions to CSV format.  It's open source but requires you to install Java before you can run it.  If anyone tries it out and runs into any issues or has any suggestions on ways to improve it please let me know.  https://github.com/MThoma202/prosper-1099-parser

[mauricev]

What good does it do to have in csv format?

[pavankumar9]

I always enter the summary of each sales category instead of going through the pain of adding each entry.  The process usually takes less than 5 minutes for me. You’ll need two pieces of info for each category to be able to do this: proceeds (1d) and cost basis(1e).

Figuring out the proceeds for each category is straight forward, as Prosper lists this at the end of each section (ex: a section with 50 entries for short-term and another section with 100 entries for long-term)

For most people, the painful part is figuring out the cost basis for each category. This is where the following approach can come in handy for folks who have basic computer programming skills:

1 - Copy the text of all transactions in a category from the PDF.

2 - Go to https://regex101.com/

3 - In the ‘Regular Expression’ box enter “Box.1e.+\$?\d+.\d+”

4 - Export all matches as text from ‘Match Information’ Section. This will give you a bunch of rows that look like “Box 1e. $13.58 .”

5 - Copy the entire text and paste it into excel.

6 - Use Find/Replace All to remove all characters that don’t belong to the cost basis: replace “Box 1e. $” with “” (Note: double quotes don’t have to be included.

7 - Select all rows and apply the sum function. Voila!! This sum is the cost basis of the category.

8 - Repeat steps 1 thru 7 for each category.

Hope this helps.

[mauricev]

This does not work at all. The Box 1e and the value for it are on different lines, totally unrelated to each other. So there's no possibility the regex can make any matches.

Here you can see a sample why can't work. 

Box 1e.
Box 1f.
Box 1g.
Box 2.
Box 4.
Box 5.
Box 7.
Box 12.
Box 13.
Box 14.
Box 16.
FATCA filing requirement
Applicable checkbox on Form 8949 B ..
$24.49 $0.00 $0.00

The $24.49 is what we're after, yet it appears on a totally unrelated line from Box 1e.