Overstock Dividend Shareholder Information

Q: Am I eligible to receive the Dividend?

A: If you are a shareholder of record, or a shareholder holding directly or indirectly through DTC, as of the Record Date (April 27, 2020) and own ten or more shares of common stock, Series A-1 or Voting Series B Preferred Stock ("Series B"), you will be eligible to receive the Dividend based on the number of shares of that class owned on the Record Date.

Q: If I hold Overstock shares in an IRA account, am I eligible to receive the Dividend?

A: Yes. Shares held in IRA's are eligible to receive the Dividend but may be subject to certain restrictions in order to make sure that the Dividend remains in the IRA and not treated as a distribution from the IRA. If there is a desire to sell the Series A-1 shares, please note that authorized custodians are able to create an account with Dinosaur Financial solely to execute sales of Series A-1 Shares, and that Dinosaur Financial itself is not an authorized custodian for IRAs. You should contact your IRA custodian for additional information about whether the custodian has any limitations on continuing to hold the Dividend in the IRA and whether it is an authorized custodian for purposes of creating an account with Dinosaur Financial.

Q: If I hold Overstock shares in a 401(k) plan account, am I eligible to receive the Dividend?

A: Yes. Shares held in 401(k) plan accounts are eligible to receive the Dividend. Certain plan custodians restrict the ability of 401(k) plan participants to elect investment in or divestment of in securities such as the Series A-1 Shares, which do not trade on a national securities exchange but is limited to trading on the tZERO ATS. You should contact your 401(k) plan custodian for additional information about any limitations on continuing to hold the Series A-1 Shares in your 401(k) plan or your ability to sell the Series A-1 Shares. Participants and beneficiaries in the Overstock 401(k) plan will receive a separate communication from Fidelity, the trustee of the plan, with further details about how the Series A-1 Shares will be handled under the plan.

Q: Do I need to have a digital wallet or must I be familiar with blockchain technology in order to receive the Dividend?

A: No. The Series A-1 Shares are not a virtual currency or another form of anonymous bearer digital instrument. The Series A-1 Shares are conventional uncertificated securities for which a "courtesy carbon copy" of certain transfer agent records are maintained on the blockchain. The courtesy carbon copy does not play any corporate or regulatory role. Rather, the traditional books and records kept by Computershare, an SEC-regulated transfer agent govern the record ownership of Series A-1 Shares. Moreover, distributed ledger technology does not play a role in the sale, issuance, transfer or custody of the Series A-1.

Q: How many Series A-1 Shares will I receive?

A: The Series A-1 Shares will be paid out at a ratio of 1:10, with one share of Series A-1 issued for every ten shares of common stock, for every ten shares of Series A-1, or for every ten shares of Series B held on the Record Date (April 27, 2020).

Q: How will fractional shares be handled?

A: Cash will be paid in lieu of fractional shares. For example, if a shareholder owns 9 shares of common stock, 9 shares of Series A-1, and 9 shares of Series B on the Record Date, such shareholder would receive cash in lieu of 0.9 fractional Series A-1 in respect to each of the shareholder's position in common stock, Series A-1 and Series B. For shareholders holding directly or indirectly through DTC, cash will be paid in lieu of fractional shares on the shareholder (beneficial owner) level.

Q: When will I receive the Dividend?

A: On the Payment Date of the Dividend, which has been set for May 19, 2020.

Q: Is this Dividend a taxable distribution?

A: No. We expect the Dividend will not be taxable for federal income tax purposes. Please see Form 8937 for more details.

Q: How do I receive the Dividend?

A: Investors are not required to take any action in order to receive the Dividend. On the Payment Date, investors should see their Series A-1 Shares reflected in their brokerage or other custodial accounts in which they hold their Overstock securities.

Q: What happens if I do nothing?

A: Investors are not required to take any action in order to receive their Series A-1 Shares As mentioned above, on the Payment Date, investors should see their Series A-1 Shares reflected in their brokerage or other custodial accounts in which they hold their Overstock securities.

Q: How do I sell the Series A-1 Shares?

A: In order to sell the Series A-1 Shares, investors must have an existing account or create an account with a Subscriber, unless the investor's current broker-dealer has created a settlement account with a Subscriber in order to carry out transactions on its clients' behalf. Once an investor establishes an account with a Subscriber, he or she will need to transfer the Series A-1 Shares from his or her existing brokerage or other custodial account to their Subscriber account. Please note that the Series A-1 Shares will be transferred using free delivery at DTC or using ACATS.

Q: How do I buy the Series A-1 Shares?

A: As with selling the Series A-1 Shares, to buy Series A-1 Shares, an investor must have an existing account or create an account with a Subscriber, unless the investor's current broker-dealer has created a settlement account with a Subscriber in order to carry out transactions on its clients' behalf.

Q: Where can I find a list of current Subscribers?

A: Please contact the Overstock Investor Relations team at ir@overstock.com for a complete list of current Subscribers, which includes Dinosaur Financial Group, LLC, an SEC-registered broker-dealer and member of FINRA and SIPC ("Dinosaur Financial") and ChoiceTrade, an SEC-registered broker-dealer and member of FINRA and SIPC ("ChoiceTrade"). tZERO ATS is continuing its efforts to expand the available Subscribers.

Q: How do I create an account with Dinosaur Financial?

A: Follow the steps below:

• Visit https://dino.tzero.com.
• Click on "Create Account"
• Follow the prompts and provide the requisite information.
• You will need to provide your address, social security number, phone number, proof of identify and other information normally required to set up a brokerage account, such as investment profile, bank account information and beneficiary information in case of death or incapacity.
• The online process takes approximately 15 to 30 minutes to fill out and submit. You should hear back from Dinosaur Financial within 24 to 72 hours regarding your application.

Q: How do I create an account with ChoiceTrade?

A: Follow the steps below:

• Visit https://www.choicetrade.com/.
• Click on "Open Account"
• Follow the prompts and provide the requisite information.
• You will need to provide your address, social security number, phone number, proof of identify and other information normally required to set up a brokerage account, such as investment profile, bank account information and beneficiary information in case of death or incapacity.
• The online process takes approximately 10 minutes to fill out and submit. You should hear back from ChoiceTrade within one business day regarding your application.

Q: How do I transfer my Series A-1 Shares into my account with Dinosaur Financial?

A: After creating an account with Dinosaur Financial, an investor must then contact his or her current broker-dealer (or other custodian), provide it with the new Dinosaur Financial account details, and initiate a transfer request. To initiate the transfer request, follow the steps below:

• After your application with Dinosaur Financial has been approved, log in to your Dinosaur Financial account.
• Obtain the following information from your current broker-dealer and input it into the Dinosaur Financial setup transfer page:
  • Current broker name.
  • Account name and number.
  • Your current broker-dealer may hold your securities at another broker-dealer, typically referred to as a "clearing firm." You will need to ask your broker-dealer if it uses a clearing firm and, if so, what that firm's name and clearing firm number are.
  • Quantity (this is the number of Series A-1 Shares to transfer from your current. broker-dealer to your Dinosaur Financial account).
• Add e-signature.
• Create a sell order through Dinosaur Financial.

How do I transfer my Series A-1 Shares into my account with ChoiceTrade?

A: After creating an account with ChoiceTrade, an investor must then contact his or her current broker-dealer (or other custodian), and obtain the following information: (1) delivering broker dealer account number, delivering clearing firm number, delivering firm name, delivering firm address and account type (i.e. individual, joint account, etc.). Once you obtain the information from your broker-dealer, please fill out this transfer form http://www.choicetrade.com/forms/ETC/Customer_Account_Transfer_Form.pdf and email it to service@choicetrade.com.

Q: When can I sell my Series A-1 Shares?

A: Series A-1 Shares can be sold at any time following receipt of such Shares on the Payment Date, which is set for May 19, 2020. However, before Shares can be sold, investors must first create an account with a Subscriber or with a broker-dealer (or other custodian) that has a settlement account with a Subscriber.

Q: When can I buy the Series A-1 Shares?

A: Series A-1 Shares currently trade on the ATS and are available for purchase now. Please note that before Shares can be purchased, investors must first create an account with a Subscriber or with a broker-dealer that has a settlement account with a Subscriber.

Q: Is there a deadline to set up an account with a Subscriber?

A: No. There is no deadline or time requirement to set up an account with a Subscriber. However, you will not be able to buy or sell the Series A-1 Shares until you set up a brokerage account with a Subscriber, or until the broker-dealer or, for purposes of selling, other custodian that holds your Overstock securities, sets up a settlement account with a Subscriber to buy or sell the Series A-1 Shares.

Q: If I don't want to set up an account with a Subscriber, is there any other way to buy or sell the Series A-1 Shares?

A: Yes, if the investor's current broker-dealer or, for purposes of selling the Series A-1 Shares, other custodian, has created a settlement account with Dinosaur Financial to facilitate trading of the Series A-1 Shares for its clients. Please visit the tZERO ATS website at www.ats.tzero.com for updated information.

Q: Do these steps apply to me if I hold my Overstock common shares in an IRA or in the Overstock 401(k) plan?

A: No. If you hold Overstock common shares in an IRA, you should see the last two questions in the following section and coordinate with the custodian for your IRA. If you hold Overstock common shares in your Overstock 401(k) account as a participant in the plan, you will receive a separate communication from Fidelity, the trustee of the Overstock 401(k) plan.

Q: How does a broker-dealer become a Subscriber to facilitate trading of the Series A-1 Shares for its own account or on behalf of its underlying investor clients?

A: Follow the steps below:

• Contact the tZERO ATS team at info@tzeroats.com.
• Execute a subscriber agreement and other requisite documents.
• Complete the onboarding process, including AML reviews and technology integration.
• Begin effecting securities transactions on the ATS for itself or on behalf of underlying investor clients, including share trades, by routing orders to the ATS for execution in the broker-dealer's capacity as a subscriber.
• Please note that the preceding is subject to any applicable regulatory review and approval.

Q: How does a broker-dealer investor facilitate trading of The Series A-1 Shares for its own account or on behalf of their underlying investor clients if it is not a Subscriber?

A: The broker-dealer can establish a settlement account with a Subscriber, on behalf of its customers.

Q: How will settlement occur for trades between accounts carried by Apex Pro?

A: Apex Pro is the clearing firm for Dinosaur Financial and ChoiceTrade, which means that it holds the securities of Dinosaur Financial's and ChoiceTrade's customers in its capacity as a regulated broker-dealer and clearing firm. If Apex Pro carries the accounts of both the buyer and the seller, transactions will be cleared and settled through the normal operations of Apex Pro on a book-entry basis on its books. Apex Pro will debit the amount of Series A-1 Shares sold from the seller's account in an amount equal to the sale price and debit a corresponding amount of cash from the buyer's account.

Q: How will settlement occur for trades in which the account of at least one party to the trade is carried by a broker-dealer other than Apex Pro?

A: We expect that trades executed on the tZERO ATS will be submitted by Apex Pro to the National Securities Clearing Corporation ("NSCC") for the Obligation Warehouse service in accordance with NSCC's rules and procedures. Apex Pro (or another counterparty) and the counterparty to the trade will be responsible for settling the trade by delivery versus payment at DTC. We also expect that certain institutional investors will settle trades in accordance with their standard settlement procedures and applicable regulatory requirements.

Q: If an IRA holder wants to sell the Series A-1 Shares received into his or her IRA, what is the process for such sales of those Shares?

A: Authorized custodians can create an account with a Subscriber. Such an account will be established in the name of the custodian and solely for execution and settlement; and the Shares will continue to be held by the IRA custodian. The authorized custodian can then enter an order to sell through its Subscriber account, and the trade will be routed to the ATS for execution.

Q: Is this Dividend a taxable distribution?

A: No, we expect the Dividend will not be taxable for federal income tax purposes, other than with respect to cash received in lieu of fractional shares. Please see Form 8937 for more details.

Q: How will settlement occur for trades executed on behalf of an IRA investment manager?

A: If the IRA custodian is a broker-dealer, we expect that trades executed on the tZERO ATS will be submitted to NSCC for the Obligation Warehouse service in accordance with NSCC's rules and procedures, and will settle by delivery versus payment at DTC, as described above.
If the IRA custodian is a bank, we expect that these trades will settle delivery versus payment at DTC and that DTCC Institutional Trade Processing's TradeSuite and Central Trade Manager systems also will be available to authorized custodians.

Q: What are the trading hours of the tZERO ATS?

A: The tZERO ATS maintains normal market hours, 9:30 am to 4:00 pm Eastern Time, Monday through Friday, excluding holidays.

Q: How will I know the price of the Series A-1 Shares?

A: Pricing information of the Series A-1 Shares is made publicly available on the tZERO ATS website, which can be found at https://ats.tzero.com/market-data.

Q: What is the process for Canadian investors to receive the Dividend?

A: If you hold Overstock securities through a broker-dealer, bank, or other financial institution, the Dividend will be deposited to the same account that holds your Overstock securities. If you are a record holder of Overstock securities, Computershare will recognize you as the owner of the Series A-1 Shares directly on the share register it maintains for Overstock. Please note that Canadian investors are not eligible to open an account at Dinosaur Financial or ChoiceTrade, but we are working to onboard additional Subscribers that will be able to accommodate Canadian investors.

Q: Will the Dividend be payable in U.S. dollars or in cryptocurrency?

A: Neither. The Dividend is a stock dividend, and the stock to be issued in the Dividend will be uncertificated securities. The stock to be paid in the Dividend is not cryptocurrency. Please note that shareholders will not be required to pay any consideration in order to receive the Series A-1 Shares. However, as mentioned above, cash will be paid in lieu of fractional shares.

Q: Will receipt of the Dividend into an IRA account constitute a distribution for tax purposes?

A: Assuming that the Dividend is not directed or paid to the IRA owner in his or her individual capacity and, instead, the Dividend is retained by the custodian for the IRA, such Dividend should not be considered a distribution of the IRA for purposes of the Internal Revenue Code.

IMPORTANT: Individuals receiving Shares into an IRA should consult with their own IRA custodians or tax advisers in determining appropriate tax treatment of the Series A-1 Shares.

Q: Who do I contact if I have additional questions about the Series A-1 Shares?

A: If you have specific questions about the Dividend, or about receiving your Series A-1 Shares, please contact Overstock's Investor Relations team at ir@overstock.com.

Q: Who do I contact for other investor-related questions about Overstock?

A: If you have other investor-related questions regarding Overstock please contact Overstock's Investor Relations team at ir@overstock.com.