Forms 1099-S for 2008 Using







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Commonwealth Land Title Insurance Company


Lawyers Title Insurance Corporation


Preparing Your

Forms 1099-S for 2008









ATTENTION: Please carefully review the

following information!

DISCLAIMER: All agents of Commonwealth Land Title

Insurance Company

and Lawyers Title Insurance

Corporation, and their employees, utilizing this manual and

those portions of the


software used to produce,

track, and record matters relating to the processing and

filing of Forms 1099-S, hereby acknowledge that full and

complete compliance with the related sections of the

Internal Revenue Code are the sole and exclusive

responsibility of said agent and their employees. Nothing

contained herein shall be construed as legal advice regarding

the processing, distribution or filing of said Forms 1099-S.

Interpretation of the Internal Revenue Code is a legal

matter; if not understood, seek competent legal advice.

IRS CIRCULAR 230 DISCLOSURE: To ensure compliance

with requirements imposed by the IRS, we wish to inform

you that, unless expressly stated otherwise, any purported

U.S. tax information contained in this communication

(including any attachments) is not intended or written to be

relied upon or used, and cannot be relied upon or used, for

the purpose of (i) avoiding penalties under the Internal

Revenue Code or (ii) promoting, marketing or

recommending to another party any transaction or matter

addressed herein.

NOTE: Those of you with incredibly good eye sight may

notice that some pictures in this manual show 2005 forms

and information. However, be assured that both




The 1099 function in Wintitle collects Seller and related closing

information from the APP and HUD screens, creating a text file of that data. You may also print Substitute 1099 forms from the HUD

screen in Wintitle. To file the actual data with the IRS, in an IRS-acceptable format, you will need to purchase and install a third-party program – we recommend 1099Express©. Once again,

Commonwealth Land Title Insurance Company and Lawyers Title Insurance Corporation is pleased to offer its agents a 20% discount for the 1099Express© software. To purchase and download your own 1099Express© program, go to the 1099Express©

homepage ( and scroll to the bottom and click on the Commonwealth/Lawyers Title Page link. You will be

prompted to enter your Commonwealth or Lawyers Title Agent ID Number and email address in order to qualify for the discount. The

1099Express© website will guide you through the download steps, and, later in these directions, we will take you through the rest of the process.



Before you begin the process of gathering and exporting the data from

Wintitle into your 1099Express© program, you will need to

determine which purchase files need to be reported. If you have been keeping track, skip ahead to ADDING AND COMPLETING 1099 DATA. If not, you will have to look through all of your 2008 purchase files to determine if the transaction must be reported or not. To help you with this task, the 1099 Manager in Wintitle will create a list of

Purchases Closed in the Year 2008. From any screen, click on


At the 1099 Manager window, pick 2008 from the dropdown and then put the black dot next to List Sales. Make sure that neither

Layout nor Preview is checked, and then click on Perform Action.

(Note: It may be necessary to reset your Printer Setup. To do this, go to File and Print Setup and select the printer you wish to use.)

Wintitle will create a list of ALL 2008 purchases – it is up to YOU to determine which of these are reportable transactions.



Before you check the information in each file, make sure that your

Company information is correct. To do this, from any screen click on

Actions, Network Options and select Company Setup from the list on the left. At the Company Setup window, you should see your office/firm name listed as the MAIN branch. (Note: If you have more than one office, you will need to decide from which office(s) you will be doing your reporting; we suggest that you use your primary office address.) In the white window, highlight the MAIN entry, as I have below.

Now, click on the Modify button (right in the middle of this window) and, at the Edit Branches window, make any necessary changes to your office/firm name, address, telephone and fax numbers. Most importantly, be sure that your Federal Tax Payer ID number is

correctly entered in the Fed ID # field. Click Save and Close to get back to Wintitle.



For each reportable file, you will have to check and/or complete

information on the APP and HUD screens. If you have not previously

supplied each Seller with a Substitute 1099 form, you will have to

print and deliver a Substitute 1099 prior to January 31, 2009. Be sure you have the actual closing files at hand as you go through the file-by-file steps.

APP Screen Information

On the APP screen, you should check to see that Seller(s) Tax ID/Social Security Number(s) were entered in the Seller/Owner

section. (Note: If your Seller has a Tax ID Number, you will be able to correct the hyphen placement during one of the HUD screen steps.) You should also enter the Seller’s forwarding address by clicking on the Address button and filling in the information as shown below.

(Note: While you do have the option of typing the Seller’s address directly on the 1099, this information will not be saved should you need to Update other 1099 information from the HUD. Entering the Seller’s forwardingaddress on the APP screen will ensure that it is saved there, on the HUD, and in your 1099 data.)


You should also look at the final HUD Settlement Statement and

Deed from your closing file. Check the deed to be sure that the

Seller(s) name(s) are correctly entered in Wintitle; if not, fix the name(s) on the APP screen. Check the HUD Settlement

Statement to make sure that no “hand-written” changes were made to the Purchase Price or Tax Adjustment, as these figures appear on the 1099. (Also check your file to see how funds were disbursed to your Seller(s); will you need to create more than one 1099?) If the

Purchase Price was changed, make the correction on the APP

screen. Be sure to click Save when finished. If the tax adjustment was changed, make the correction on the HUD and Save.

HUD Screen Information

If you have made any changes on the APP screen which will impact the HUD Settlement Statement (Seller name(s), address, TIN, or purchase price), you should click Modify HUD to see that the changes have carried over to the Settlement Statement, and then Save and exit. (Remember, the 1099 pulls most of its information from the

HUD Settlement Statement!)

It is worth noting that you CAN make changes and add information directly in the 1099 S window (which we will explore next), but this information will not be saved to the rest of the program, and will be deleted from the 1099 when you pull the HUD information from the

Settlement Statement to the 1099, using the Refresh from HUD

button. Therefore, following the above steps for each file (preferably before printing the Substitute 1099-S at closing, but definitely before using 1099Express© to prepare your year-end reports) is preferable.


USING THE 1099 S FEATURES The 1099 S Window

On the HUD screen of Wintitle, you will see the 1099 button (with a picture of a printer and “1099” on it), located to the right of the “print”

Checks button. Click on the 1099 button, and you will see the 1099 S window, as shown below.

Not Reportable:

If and when you determine that this is not a reportable transaction, you should check the Void box at the top of the 1099 S window. In this way, when you create your list of 1099s (See List 1099 below), you can mark this file and delete it when the information has been imported into 1099Express©.

Reportable Transactions:

Check the FILERS box to make sure that your office/firm information is correct. Check to see that your TIN (tax payer identification

number) has pulled into the FILERS Federal Tax ID field. Check to see that TRANSFEROR’S SSN has pulled from the APP screen. (Note: The program will pull the “first” seller’s Social Security Number that it sees, so in the case of couples filing jointly, you will


want to have at least one number entered. For unmarried sellers, or for those who are married, filing separately, you may need to create more than one 1099 for the transaction – those directions will follow.) Check the TRANSFERORS fields to see that the Seller name(s) and address have pulled correctly from the APP screen. The Account Number field will be populated by your File Number. Box 1 will pull the Closing Date; Box 2 will pull the Seller’s Gross Proceeds


purchase price); and Box 3 will pull the subject Property Address. Box 5 will pull any real estate tax adjustment credited to Seller. Before using any of the other 1099 feature buttons, you should now click on the Refresh from HUD button, located at the bottom of the right-hand column of buttons. This will pull any missing or revised information from the HUD Settlement Statement. Please also be sure that Prompt ON is checked (located at the bottom of the column of buttons); this will ensure that the Print window in Word

will open any time you wish to print something from this window.

The 1099 S Features


To print a Substitute 1099-S form, click the Print button.

You may give this Substitute 1099-S to the Seller(s) at closing, thus eliminating the need to send out forms to individuals at year-end. Note that Wintitle will enter the dated you printed the Substitute 1099-S in the Date Printed/Exported box, under Original. (You can see in the above screen shot that I printed my sample Substitute 1099-S on 11/17/05 – the date appears in blue.)

If you need to create more than one 1099 record for a file (for those transactions in which you have more than one unmarried seller or your married sellers file separately), you should click on the Add New button. This will create a duplicate record, which you will then need to edit (along with the “original”) in order to reflect the correct Seller name, address, TIN, and appropriate portion of the Gross Proceeds. (NOTE: When you click Add New, the first field in the FILERS section will be highlighted – you should Tab from field to field, changing only those sections necessary to create the second

1099 record. Once you have created the second record, click Save and Exit. Now, when you click on the 1099 button, you will get a

“list” of all 1099 records, and you can chose the first and edit that accordingly.)


From the 1099 Selection window, you could add a third record by clicking on Add New, and so on.

(There does not appear to be a way to delete a second record, should you create one unnecessarily (as I did in this file where the Seller is a trust), so when you are “practicing” your 1099 skills, be sure to practice on a “test” file!)


Every time you wish to exit the 1099 S window, you should use the

Save and Exit button. If you make changes to the 1099, but then wish to cancel those changes and revert to the information pulled from the APP and HUD screens, click the Cancel Changes button. PLEASE avoid the Report Layout button, which brings you into the actual

1099 template; if you are burning with curiosity, here is what it looks like (below). If you actually click on the button, click on the fox in the corner of that window to Close. Please do not alter the template!

Other 1099 Manager Features

At the beginning of these directions, we looked to the 1099 Manager

to create a list of all purchases closed in 2008 (see Determining Which Files Get Reported, above). You can also use the 1099 Manager to:


Print 1099

This feature will allow you to print (as a single batch) ALL Substitute 1099s for the selected year. To do this, from any screen, click on

File, and select 1099 Manager from the dropdown. On the 1099 Manager window, pick 2008 from the dropdown and put the black dot next to Print 1099. (Make sure that neither Layout nor Preview

is checked, unless you wish to preview the forms.) Click on Perform Action.

(Note: Once again, it may be necessary to reset your Printer Setup. To do this, go to File and Print Setup and select the printer you wish to use.)

Export 1099


List Sales


List 1099

This feature allows you to print a list of those purchase files for which you have created a Substitute 1099. To do this, from any screen, click on File and from the dropdown, select 1099 Manager. At the

1099 Manager window, pick 2008 from the dropdown and then put the black dot next to List 1099. Make sure the neither Layout nor

Preview is checked, and then click on Perform Action. You will produce a report called 1099 To Be Reported for the Year 2008.



: This list should


be used to determine if a

transaction is reportable. Only you can make that

determination, based upon current


regulations and

information gathered at closing.)



The most important feature of the 1099 Manager in Wintitle (at least from a year-end perspective) is the Export 1099 feature. You should only use the feature AFTER you have added and

completed all 1099 data AND AFTER you have purchased and downloaded 1099Express.

When you are ready to export your 1099 data, from any screen click on File and select 1099 Manager from the dropdown. At the 1099 Manager window, pick 2008 from the dropdown and then put the black dot next to Export 1099. Make sure that neither Layout nor

Preview is checked, and then click on Perform Action.

This will export all previously unexported 1099 records to a text file

and update the 1099 record with the current date. When you click on

Perform Action, you will receive a Wintitle “message” telling you that the Export File was created – you should then click on OK. (See example on the following page.)


(Note: My Export File is called

“C:\\WINTITLE\DEWEYCHE\TEN99\EX051208.TXT”, as you may, or may not, be able to see in the preceding example. The EX portion of the file is the date on which you did the export, as YYMMDD – I did this on December 8, 2005.)

The text file that is created will be written to a TEN99 folder, located in your Company folder, which is in your Wintitle folder. The

Wintitle “message” will give you the “path” to this folder, which you can locate using Windows Explorer (more on that later).


USING 1099Express©


At this point, you need to have the 1099Express© program

downloaded on your computer. To get the 2008 program, go to and click the DOWNLOADS link at the top left and follow the download/install directions. After installation, your new desktop icon will look like this:

To purchase the program (which can be done after downloading) go to the home page at If this is your first year using 1099Express©, the cost is $159.00 for Commonwealth and

Lawyers Title agents - a discount of 20%! New users should scroll down the home page to the link that says "Commonwealth/Lawyers Title Page", where you will enter your Agent ID Number and email address, and check out from there. If you are renewing your

subscription, go to the same home page, click the ORDER link at the top and choose the 1099 Software for Previous Customers $99.00



When you see the screen shown above, you are ready to transfer your

Wintitle data to 1099Express©for filing with the IRS!

At this point, you will be in the capable hands of the wonderful folks at

1099Express©! You may reach them by telephone at (361) 884-1500, you may email your technical or support questions to, or simply click on the Help buttons (see previous screen shot) for written instructions on all topics.

Using the File/Open Menu to Open Your Wintitle Export File

Let’s suppose that the export file to open into 1099Express© is: c:\WINTITLE\DEWEYCHE\TEN99\EX051117.txt. (Note: Your file will contain your firm name or “law office” after “Wintitle\” and your “EX” designation will contain the year, month, and day of the date on which you create the Export file.)

In order to find that Export file, from the 1099Express© toolbar, click on File and from the dropdown, select Open or click on the Open

button (upper left, under File). The Open window (shown below) will appear.


At the top of the Open window, next to Look in, use the dropdown and find Local Disk (C:). Find the Wintitle folder and double-click on it. From that file list, find your firm name/LAW OFFICE file

(mine is DEWEYCHE, short for Dewey, Cheatham & Howe) and double-click on that. From that file list, find the TEN99 folder and double-click on that. Use the dropdown next to Files of Type to select

All files (*.*). You will see a list of all of the export files that you have created. Highlight the one you intend to use for sending your reportable 2008 information to the IRS and click the Open button on the Open window.

Opening the Export file will transfer your Wintitle data to the

1099Express© program and you will see a screen similar to the one


Validating the Export Data

In order to be sure that your Wintitle information will comply with

IRS specifications, please do the following:

Step 1: From the 1099Express© grid, select the first name in the

Name column and double-click on it. This will bring up the 1099-S Data Entry Form window, which is, in fact, a picture of the

Recipient’s 1099-S form.

Check to be sure the data placement looks correct, and then click

Cancel to close the form. You need only do this once, with the first entry. (NOTE: You will notice that the Filer’s box is empty; that is okay for now – it will be filled in when we add your Company


Step 2: From the 1099Express© toolbar, click on Options and select Verify Format from the dropdown menu. This automatically verifies ALL records, to be sure that they conform to IRS specifications. If everything is in order, a Format Check OK message will appear.

If you receive a message indicating that the data contains errors, you should click on the “List” Button to determine what needs to be fixed. If there are a large number of errors, you may wish to correct them inside Wintitle and re-export the file. If the problems are very minor, they can be corrected, on the spot, inside 1099Express©. To do this,

once again click on Options in the 1099Express© toolbar and select Correct from the dropdown menu. (For example, if you receive a message saying “Invalid State” and the Recipient’s address is in Canada, then click the “Foreign” checkbox on the 1099Express©

data form, then OK. Save the file and you are ready to go!)

Adding Your “Company” Information

To add your office/firm information, click on the FILER button, located in the upper left corner of the grid (or you can click the Option/Filer menu). You will see a "Tabbed" window, with tabs labeled "Payer's ID No.", "Names", "Special", and "RE-Populate". Insert the Tax year (2008), and your firm's Tax ID Number on the first tab, then click


Saving Your 1099Express© Source File

After your Company information has been entered, double-click on any line in the grid to view the 1099-S form again. Verify that the

Company information is displayed correctly, and then close the form. Now, click on File in the 1099Express© toolbar and select Save from

the dropdown menu (or you may use the Save button with the picture of a floppy disk). All of your 1099 data will be saved back into the

TEN99 folder. (Note: Please use Save, and not Save As, so that the information is always saved to the TEN99 folder.)

Filing with the IRS

When you are ready to file your 2008 records with the IRS, there are three (3) different options:

1. Filing by paper (See Help/Index, Topic No. 7 and Topic No. 8); 2. Filing via the Internet (See Help/Index, Topic No. 10); and 3. Filing via the 1099Express© Service Bureau, (See Help/Index,

Topic No. 9).

As you may know, you must use options 2 or 3 (not paper) if you have over 250 reportable records, or be subject to IRS penalties. (Note: The filing limits may change for each new tax year – you should always review the IRS filing requirements.) Even if you have less than 250 reportable records, you may still choose options 2 or 3 to avoid making a paper filing.

As with all aspects of using 1099Express©, you should defer to them

for directions and guidance with any questions that you may have. The screenshots and outline, herein provided, show you what I encountered in the process. Good luck!



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