Exhibit 10.1

TOLLING AND STANDSTILL AGREEMENT

THIS TOLLING AND STANDSTILL AGREEMENT (this “Agreement” ) is made and entered into by Overstock.com, Inc. ( “Overstock” ) and the Overstock.com, Inc. Employee Benefits Committee (the “Committee” ), on behalf of the Overstock.com, Inc. 401(k) Plan (the “Plan” ), on and to be effective as of August 31, 2009.

WHEREAS, Overstock has determined that it may have issued more shares of its common stock ( “Common Stock” ) to the Plan for the benefit of Plan participants than have been registered with the Securities and Exchange Commission for issuance to or in connection with the Plan; and

WHEREAS, Overstock desires to make a rescission offer to affected participants in the Plan who acquired shares of Overstock Common Stock between July 1, 2008 and June 30, 2009 but has determined that it is unable to do so at the present time; and

WHEREAS, the Committee serves as the Administrator of the Plan, and is authorized to take such actions with respect to the Plan as may be deemed necessary or appropriate by the Committee; and

WHEREAS, the Committee, on behalf of the Plan, and Overstock (the “Parties” ) desire to protect any rights of the Plan or its participants that may exist at June 30, 2009 by ensuring that any such rights are not prejudiced due to any Time-Related Defenses (as defined in paragraph 6(b)) that may be asserted as to any Claims (as defined in paragraph 6(a));

NOW THEREFORE, the Parties agree as follows:

1.  Period of Forbearance . Except as otherwise agreed by the Parties, the Plan and the Committee shall forbear and postpone the filing, commencement, and prosecution of Claims, if any, against Overstock for the period of time (the “Period of Forbearance” ) commencing on the date hereof and continuing until the earlier of (a) the termin