On April 19, 2012, the SEC instituted an administrative proceeding against OX Trading, LLC, optionsXpress, Inc., and Thomas E. Stern. According to the SEC, OX Trading violated securities laws by trading in securities despite the fact that they "ceased being a member of CBOE" on March 2, 2009. Furthermore, it is alleged that "Stern and optionsXpress caused and willfully aided and abetted OX Trading's violations of Sections 15(a) and 15(b)(8) of the Exchange Act."

On April 19, 2012, the SEC announced in a Press Release that: "The Securities and Exchange Commission today charged a Chicago-based securities dealer affiliated with online brokerage firm optionsXpress with violating the registration provisions of the securities laws when it continued trading operations after delisting from the Chicago Board Options Exchange (CBOE) and deregistering with the SEC, apparently to avoid an audit."

On September 5, 2012, Chief Administrative Law Judge Brenda P. Murray granted the SEC Division of Enforcement's Motion for Partial Summary Disposition. Chief Administrative Law Judge Murray noted that : "The allegations do not involve fraud or harm to customers, but whether a business entity was required to register with the Commission."

On January 16, 2013, Brenda P. Murray, the Chief Administrative Law Judge, filed a motion to the Commission for extension of "the deadline for an Initial Decision for six months."

On April 13, 2013, the Commission granted the motion of Chief Administrative Law Judge Brenda P. Murray for an extension of time until August 19, 2013 to issue the initial decision in the proceeding.

On July 1, 2013, Chief Administrative Law Judge Brenda P. Murray requested to the Commission a second extension on the August 19, 2013 due date for the Initial Decision pursuant to Rule 360(a)(3).

On August 7, 2013, the SEC issued an order extending the deadline for filing the initial decision in this matter to February 19, 2014. Chief Administrative Law Judge Brenda P. Murray moved for the extension of time.

On September 6, 2013, Chief Administrative Law Judge Brenda P. Murray granted a request to postpone an exchange of information under a prior procedural schedule in which the parties to a April 19, 2012, SEC Order Instituting Administrative and Cease-and-Desist Proceedings agreed "to exchange (i) the names of their witnesses, (ii) the identity of any experts, and (iii) either a list or copies of their exhibits by September 6, 2013."

On September 16, 2013, Chief Administrative Law Judge, Brenda P. Murray, issued an order staying the proceedings pursuant to a September 13, 2013 Joint Motion to Stay the Proceedings for SEC Consideration of Offers of Settlement (Motion) pursuant to Commission's Rule of Practice 161(c)(2). The SEC filed the motion to stay proceedings because "the Division of Enforcement has received signed Offers of Settlement from two Respondents and it expects to receive one from the third Respondent, which it will recommend the Commission accept."

On October 22, 2013, the SEC filed settled administrative proceedings against OX Trading, LLC. According to the SEC: "These proceedings arise out of registration violations relating to OX Trading, LLC ('OX Trading'), which, during the relevant period, was a subsidiary of optionsXpress Holdings, Inc. ('Holdings'). OX Trading was formed in 2007 to provide customers of optionsXpress, Inc. ('optionsXpress'), a registered broker-dealer that was also a subsidiary of Holdings, price improvement on their orders via internalization of options trades."