State orders ClearShare to cease and desist insurance operations in Oregon; warns consumers on non-ACA plans

Page 1 of 11 – FIRST AMENDED NOTICE ORDER CLEARSHARE HEALTH - INS-26-0024
Division of Financial Regulation
Telephone: (503) 378-4387
STATE OF OREGON
DEPARTMENT OF CONSUMER AND BUSINESS SERVICES
DIVISION OF FINANCIAL REGULATION
In the Matter of:
CLEARSHARE HEALTH; CLEARWATER
BENEFITS LLC; DOUGLAS SHERMAN;
CLEARWATER BENEFITS
ADMINISTRATORS, LLC; and
CLEARWATER BENEFITS HOLDINGS,
LLC,
Respondents.
Case No. INS-26-0024
FIRST AMENDED ORDER TO
CEASE AND DESIST, PROPOSED
ORDER TO REVOKE LICENSES,
AND NOTICE OF RIGHT TO A
HEARING
The Division of Financial Regulation (“DFR”), acting on behalf of the Director of the Department of Consumer and Business Services for the State of Oregon (the “Director”), conducted an investigation of ClearShare Health, Clearwater Benefits LLC, Douglas Sherman, Clearwater Benefits Administrators, LLC, and Clearwater Benefits Holdings, LLC (“Respondents”). DFR determined that Respondents violated certain provisions of Oregon Revised Statutes (“ORS”) chapters 731, 732, 733, 734, 735, 737, 742, 743, 743A, 744, 746, 748, and 750 (“Insurance Code”) and the Oregon Administrative Rules (“OAR”) promulgated under those laws. The Director issues the following Findings of Fact, Conclusions of Law, Order to Cease and Desist, Proposed Order to Revoke Licenses, and Notice of Right to an Administrative Hearing. FINDINGS OF FACT The Director FINDS that:

1. ClearShare Health (“ClearShare”) is a Missouri nonprofit corporation
   incorporated on April 25, 2022. Its principal place of business is located at 14425 Falcon Head Blvd, Bldg. E, Ste. 100, Austin, TX 78738-4412. The Director has not issued a certificate of authority to ClearShare to transact business as an insurer in Oregon.
2. Clearwater Benefits LLC (“CB”) is a Texas limited liability company formed
   on or about May 1, 2018. Its principal place of business is located at 14425 Falcon Head

Page 2 of 11 – FIRST AMENDED NOTICE ORDER CLEARSHARE HEALTH - INS-26-0024
Division of Financial Regulation
Telephone: (503) 378-4387
Blvd, Bldg. E, Ste. 100, Austin, TX 78738-4412. CB, whose National Association of Insurance Commissioners (“NAIC”) national producer number (“NPN”) is 18891588, has held an Oregon non-resident insurance producer license since January 1, 2026 (the “CB License”). CB is a sales agency that sells ClearShare medical plans in Oregon and other states, and promotes the sale of ClearShare, which it markets through, among other means, its maintenance of a website (located at https://ClearSharehealth.org) and LinkedIn page (located at https://www.linkedin.com/company/clearwater-benefits).
3. Douglas Sherman (“Sherman”) is a resident of the State of Texas, and co-founder
of CB. Sherman also holds an Oregon non-resident insurance producer license (the “Sherman License”). Sherman’s NPN is 18339407, and he was first licensed as an Oregon non￾resident insurance producer on May 2, 2024. As CB’s CEO, Sherman is responsible for overseeing the sale of ClearShare medical plans in Oregon and other states.
4. Clearwater Benefits Administrators, LLC (“CBA”) is a Delaware limited
liability company formed on or about May 4, 2022. Its principal place of business is located at 10808 Split Stone Way, Austin, TX 78739. CBA provides third party administrator services for ClearShare’s medical plans, including in Oregon. CBA does not hold and has never held a third party administrator license in Oregon.
5. Clearwater Benefits Holdings, LLC (“CBH”) is a Delaware limited liability
company formed on or about May 23, 2023. Its principal place of business is located at 1301 S. Capital of Texas Hwy, Ste. B202, Austin, TX 78746. CBH is a holding company that owns 100% of Clearwater Benefits LLC and 90% of CBA and retains employees for shared services with CB and CBA that include marketing, executive, and accounting staff.
6. ClearShare holds itself out as a “healthshare” that sells “memberships” to
individuals seeking to pool resources to meet the collective members’ healthcare needs. ClearShare memberships are open to consumers that meet the criteria set forth in the membership guidelines, adhere to the ClearShare Statement of Beliefs, and submit monthly

Page 3 of 11 – FIRST AMENDED NOTICE ORDER CLEARSHARE HEALTH - INS-26-0024
Division of Financial Regulation
Telephone: (503) 378-4387 payments (which it refers to as “contributions”). ClearShare’s Articles of Incorporation, filed with the Missouri Secretary of State on April 25, 2022, include the following statement: “Individuals pay their monthly contribution, and medical needs are shared as they arise.”
7. Clearwater’s website advertises ClearShare products, which it purports provide
“[h]igh-quality, affordable healthcare,”1
“major medical insurance,” and “supplemental insurance.”3
8. ClearShare offers at least four different ClearShare products for sale:
ClearShare 2500, HAS + ClearShare 2500, Basic + ClearShare 2500, and Advanced + ClearShare 2500.
9. In a consent order with the Washington State Office of the Insurance
Commissioner that it executed December 2, 2025, ClearShare conceded that its plan types vary from Single, Married, Single w/ Kids, and Family, and cost approximately $284 to $969 per month. The plans have a variety of health care services that are shareable after the “Annual Maximum,” shareable with limitations (such as an amount of visits or maximum amount), and ineligible for sharing according to the membership guidelines.
10. Under the ClearShare Membership Guidelines, which are posted on its
website, the “Annual Maximum,” ranging from $1,000, $2,500, and $5,000, is the amount that a member pays before the ClearShare community shares in medical expenses. The guidelines state:
All qualifying medical expenses submitted after the Annual Maximum is met are shareable with the ClearShare community up to 100% of the usual and customary charge determined by ClearShare. There is no annual or lifetime limit. You will not need to pay the Annual Maximum again until the new plan year begins. Additionally, you are only responsible for the Annual Maximum once each plan year. 1 Accessed at: https://www.clearwaterhealth.com. 2 C.f., https://www.clearwaterhealth.com/individuals/plans/major-medical. 3 Accessed at: https://www.clearwaterhealth.com/individuals/plans/supplemental-insurance. 4 C.f., https://ClearSharehealth.org/for-members

Page 4 of 11 – FIRST AMENDED NOTICE ORDER CLEARSHARE HEALTH - INS-26-0024
Division of Financial Regulation
Telephone: (503) 378-4387
11. ClearShare also offers “Basic Add-on”
and “Advanced Add-On”6 plans, which include some shareable services that do not accumulate towards the “Annual Maximum.”
12. Under the ClearShare Membership Guidelines, ClearShare refers to members’
medical expense requests as “Needs.” Members used to submit “Needs” to ClearShare using an online “Needs Request” form. However, ClearShare now provides its members with an “ID card,” and instructs its members, “Tell your provider to follow the instructions on your ID card to send us medical bills.”7
13. Under the ClearShare Membership Guidelines, ClearShare explains its process
for appealing nonpayment of medical expenses for a member who “believes that a limitation was incorrectly placed on member sharing.” The “appeals are reviewed monthly by a committee that includes at least one ClearShare board member.”
14. Under the ClearShare Membership Guidelines, ClearShare provides a detailed
list of the medical services that are covered and other benefits, which include general medicine consultations, end of life assistance, maternity needs, and many others. There are also descriptions of services that are not covered, such as preexisting conditions and abortion services.
15. The “FAQ” page of the ClearShare website includes the following question:
“What is ClearShare?” The website’s response to this question includes the statement:
“ClearShare is not insurance.”
16. As of March 29, 2026, there were 370 Oregonians enrolled as members with
ClearShare, which was comprised of 180 primary members and 190 dependents. /// 5 The terms of this membership may be accessed at:
https://ClearSharehealth.org/hubfs/Clear%20Share%20Health/For%20members/BasicClearShare-Member￾Guidelines-1.pdf 6 The terms of this membership may be accessed at:
https://ClearSharehealth.org/hubfs/Clear%20Share%20Health/For%20members/AdvancedClearShare￾Member-Guidelines-1.pdf. 7 https://ClearSharehealth.org/need-request

Page 5 of 11 – FIRST AMENDED NOTICE ORDER CLEARSHARE HEALTH - INS-26-0024
Division of Financial Regulation
Telephone: (503) 378-4387
CONCLUSIONS OF LAW
The Director CONCLUDES that:
17. Pursuant to ORS 731.102(1), “Insurance” means a contract whereby one
undertakes to indemnify another or pay or allow a specified or ascertainable amount or benefit upon determinable risk contingencies.
18. Pursuant to ORS 731.146(1), “Transact Insurance” means:
(a) Making or proposing to make an insurance contract.
(b) Taking or receiving any application for insurance.
(c) Receiving or collecting any premium, commission, membership fee, assessment, due or other consideration for any insurance or any part thereof. (d) Issuing or delivering policies of insurance. (e) Directly or indirectly acting as an insurance producer for, or otherwise representing or aiding on behalf of another, any person in the solicitation, negotiation, procurement or effectuation of insurance or renewals thereof, the dissemination of information as to coverage or rates, the forwarding of applications, the delivering of policies, the inspection of risks, the fixing of rates, the investigation or adjustment of claims or losses, the transaction of matters subsequent to effectuation of the policy and arising out of it, or in any other manner representing or assisting a person with respect to insurance. (f) Advertising locally or circularizing therein without regard for the source of such circularization, whenever such advertising or circularization is for the purpose of solicitation of insurance business. (g) Doing any other kind of business specifically recognized as constituting the doing of an insurance business within the meaning of the Insurance Code. (h) Offering a multistate qualified health plan to individuals or small employers through the program administered by the United States Office of Personnel Management pursuant to 42 U.S.C. 18054. (i) Doing or proposing to do any insurance business in substance equivalent to any of paragraphs (a) to (h) of this subsection in a manner designed to evade the provisions of the Insurance Code.
19. ClearShare’s membership plans are a contract between ClearShare and
consumers, in which ClearShare undertakes to pay specific and ascertainable amounts of

Page 6 of 11 – FIRST AMENDED NOTICE ORDER CLEARSHARE HEALTH - INS-26-0024
Division of Financial Regulation
Telephone: (503) 378-4387 members’ determinable risk contingencies in the form of medical expenses, after the members pay their Annual Maximums (which are really just insurance deductibles by another name). Therefore, ClearShare’s membership plans meet the definition of “Insurance” in Oregon pursuant to ORS 731.102(1), and because ClearShare had entered into at least 180 insurance contracts, while also offering the plans for sale on its website, ClearShare is also transacting insurance in Oregon, pursuant to ORS 731.146(1).
20. Pursuant to ORS 731.354, no person shall act as an insurer and no insurer shall
directly or indirectly transact insurance in this state except as authorized by a subsisting certificate of authority issued to the insurer by the Director.
21. By transacting insurance as an insurer in Oregon, ClearShare did violate, and
continues to violate, ORS 731.354.
22. Pursuant to ORS 744.074(1)(g), the Director may place an insurance producer
licensee on probation or suspend, revoke, or refuse to issue or renew an insurance producer license, and may take other actions authorized by the Insurance Code in lieu thereof or in addition thereto, if a licensee commits unfair trade practices or fraud related to insurance.
23. CB and Sherman both knew or should have known that ClearShare was selling
insurance in this state without a certificate of authority. By representing that “ClearShare is not insurance,” CB and Sherman did violate and continue to violate ORS 744.074(1)(g), which supports the revocation of both the CB License and the Sherman License by the Director.
24. Additionally, both CB and Sherman, in acting as insurance producers in
Oregon, are transacting insurance in Oregon, pursuant to ORS 731.146(1).
25. Pursuant to ORS 744.702, a person shall not transact business or purport or
offer to transact business as a third party administrator in Oregon unless the person holds a third party administrator license issued by the Director.
26. CBA does not and has never held a third party administrator license in Oregon,

Page 7 of 11 – FIRST AMENDED NOTICE ORDER CLEARSHARE HEALTH - INS-26-0024
Division of Financial Regulation
Telephone: (503) 378-4387 but has offered and continues to offer such services in this state for the purposes of administering ClearShare insurance plans. Therefore, CBA has violated and continues to violate ORS 744.702. Furthermore, because CBH retains employees for shared services with CBA that include marketing, executive, and accounting staff, to the extent that CBH employees have assisted CBA with providing third party administrator services in Oregon without a license, CBH has also violated and continues to ORS 744.702.
27. Additionally, both CBA and CBH (to the extent that it is assisting CBA with
providing third party administrator services in Oregon) are transacting insurance in Oregon, pursuant to ORS 731.146(1).
28. Pursuant to ORS 731.022, no person shall transact insurance in Oregon without
complying with the applicable provisions of the Insurance Code.
29. By engaging in violations of ORS 731.354 while transacting insurance in
Oregon, ClearShare has violated and continues to violate ORS 731.022. By engaging in violations of ORS 744.074(1)(g) while transacting insurance in Oregon, CB and Sherman have violated and continue to violate ORS 731.022. By engaging in violations of ORS
744.702 while transacting insurance in Oregon, CBA and CBH have violated and continue
to violate ORS 731.022.
30. Pursuant to ORS 731.252(1), whenever the Director has reason to believe that
any person has been engaged or is engaging or is about to engage in any violation of the Insurance Code, the Director may issue an order, directed to such person, to discontinue or desist from such violation or threatened violation.
31. Because the Director has reason to believe that all Respondents have been
engaged and are continuing to engage in various violations of the Insurance Code, the Director may issue an order to Respondents to cease and desist under ORS 731.252(1). /// ///

Page 8 of 11 – FIRST AMENDED NOTICE ORDER CLEARSHARE HEALTH - INS-26-0024
Division of Financial Regulation
Telephone: (503) 378-4387
ORDER TO CEASE AND DESIST
32. The Director issues the following ORDER: Pursuant to the authority of ORS
731.252(1), the Director hereby ORDERS Respondents to CEASE AND DESIST from:
A. Transacting insurance in Oregon, including but not limited to:

• marketing, offering, or selling ClearShare memberships to Oregon
  residents;
• soliciting, collecting, or receiving any consideration, contribution, fee, or
  payment from Oregon residents for new ClearShare memberships or renewals of existing ClearShare memberships;
• representing that ClearShare memberships do not meet the legal
  definition of or otherwise qualify as insurance, major medical coverage, supplemental insurance, or any related insurance product, or that ClearShare memberships are not subject to the regulation and oversight of the Director. B. Engaging in any conduct that violates ORS 731.354, 731.022, 744.074, or ORS
  744.702. Limited Carveout for Existing Members: Notwithstanding the
  prohibitions above, Respondents may continue to administer medical expense submissions arising from ClearShare memberships that were in effect as of the date of this Notice Order, including processing, adjudicating, and paying such submissions.

33. This Order to Cease and Desist is effective immediately and will remain in
    effect subject to further order of the Director.
    ///
    ///
    ///
    ///

Page 9 of 11 – FIRST AMENDED NOTICE ORDER CLEARSHARE HEALTH - INS-26-0024
Division of Financial Regulation
Telephone: (503) 378-4387
PROPOSED ORDER REVOKING INSURANCE PRODUCER LICENSES
34. Pursuant to ORS 744.074(1)(g), the Director hereby PROPOSES to REVOKE
both CB and Sherman’s non-resident insurance producer licenses, also referred to herein as the CB License and the Sherman License. DESIGNATION OF RECORD
35. Pursuant to ORS 183.417, the Director designates the Director’s file on this
matter, which includes any materials submitted by Respondents, as the record in this case. In accordance with OAR 137-003-0670(3)(a)-(b), the record contains sufficient evidence of the existence of facts necessary to support a final order by default should the Director issue such an order. IT IS SO ORDERED. Dated this 24th day of April, 2026. Sean E. O’Day, Director Department of Consumer and Business Services _______________________________________ Dorothy Bean, Chief of Enforcement Division of Financial Regulation [Remainder of this page left intentionally blank]

Page 10 of 11 – FIRST AMENDED NOTICE ORDER CLEARSHARE HEALTH - INS-26-0024
Division of Financial Regulation
Telephone: (503) 378-4387
NOTICE OF RIGHT TO AN ADMINISTRATIVE HEARING
As provided by the Oregon Administrative Procedures Act, ORS Chapter 183, any respondent affected by the foregoing is entitled to a formal contested case hearing before an Administrative Law Judge assigned by the Office of Administrative Hearings. In accordance with ORS 183.415, a respondent must file a written request for a contested case hearing within 20 days from the date the order was served personally, or by registered or certified mail. An order that is served by registered or certified mail is complete and effective on the date it is mailed to the correct address, even if it is not received by the person to be notified or if that person fails or refuses to accept service of the order. If a respondent does not timely file a hearing request, their right to a hearing shall be considered waived. A written hearing request should be directed to:
Department of Consumer and Business Services
Division of Financial Regulation
350 Winter Street NE, Room 410
Attn: Alex Gund alex.gund@dcbs.oregon.gov
In accordance with OAR 137-003-0550(1), a respondent that is a natural person may submit a hearing request without the assistance of an attorney. Subject to exceptions, any hearing request that is submitted on behalf of a corporation, partnership, limited liability company, unincorporated association, trust or governmental body (“Entity Respondent”) by a person that is not licensed to practice law in Oregon must be ratified, in writing, by a person that is allowed to practice law in Oregon within 28 days from the day the hearing request was received by the Director. In that circumstance, the filing date will be determined by the date the hearing request was received, not the ratification date. A hearing request that is not properly ratified will be deemed invalid. Any respondent that requests a hearing will be notified of the time and place of the hearing. They will also be provided with information on procedures, right of representation, and other rights of parties relating to the conduct of the hearing before the commencement of the hearing. Any hearing will be held by an administrative law judge from the Office of Administrative Hearings, assigned as required by ORS 183.635 and conducted pursuant to the contested case procedures as described in ORS 183.310 through ORS 183.550. Pursuant to OAR 137-003-0550, a respondent that is a natural person may represent themselves in the hearing or be represented by an attorney or other representative as authorized by federal or state law. An Entity Respondent must be represented by an attorney. Subject to exceptions, any attorney that represents a respondent in a contested

Page 11 of 11 – FIRST AMENDED NOTICE ORDER CLEARSHARE HEALTH - INS-26-0024
Division of Financial Regulation
Telephone: (503) 378-4387 case hearing must be licensed to practice law in Oregon. A legal aid organization may be able to assist a party with limited financial resources. The Director may issue a final order by default against any respondent that: 1) does not request a hearing within 20 days; 2) withdraws a request for a hearing; 3) notifies the Division or the administrative law judge that they will not appear; 4) fails to appear at the scheduled hearing; or 5) in the case of a request for hearing by an Entity Respondent that is not signed by a person that is allowed to practice law in Oregon, an Entity Respondent that submits a hearing request that is invalid because the request was not ratified by an attorney that is allowed to practice law in Oregon, in writing, within 28 days of the date that the hearing request was received by the Division. NOTICE TO ACTIVE DUTY SERVICEMEMBERS Active duty servicemembers have a right to stay these proceedings under the federal Servicemembers Civil Relief Act. For more information contact the Oregon State Bar at 800-452-8260, the Oregon Military Department at 503-584-3571 or the nearest United States Armed Forces Legal Assistance Office through http://legalassistance.law.af.mil. The Oregon Military Department does not have a toll free number. STATEMENT OF REASONABLE ACCOMMODATION All proceedings will be conducted in a wheelchair accessible location. Written materials may be provided and/or graphic displays may be presented during the proceeding. For any other accommodation needed by individuals due to a disability, please contact the agency staff person noted below. AGENCY CONTACT INFORMATION Questions concerning the issues raised in the order may be directed to Alex Gund, Oregon Department of Consumer and Business Services, Division of Financial Regulation, Enforcement Section, telephone (971) 707-0327.