Lawyers

Caleb Chaplain, Esq.

For more than a decade, Caleb served as the career law clerk to the Honorable Rebecca B. Connelly of the U.S. Bankruptcy Court for the Western District of Virginia. He also clerked for the Honorable Paul M. Black, giving him insight into how bankruptcy judges approach cases across the region.

In addition to practice, Caleb teaches Bankruptcy Law as an adjunct professor at Washington and Lee University School of Law. He is a frequent speaker at bankruptcy conferences and was honored by the American Bankruptcy Institute as a “40 Under 40” recipient.

A Rockingham County resident, Caleb is deeply connected to his community. He serves as Board President for the Second Home Learning Center and volunteers with local arts and LGBTQ+ organizations. His mix of legal expertise and service reflects Caleb’s steady belief that all people deserve clarity and compassion when facing financial stress.

Education

Indiana University Maurer School of Law, J.D.
Dartmouth College, B.A.

Memberships

American Bankruptcy Institute
Bankruptcy Law Section of Virginia State Bar, Newsletter Editor
American Bankruptcy Institute Journal, Coordinating Editor
WORKOUT
Harrisonburg-Rockingham Bar Association

Caleb Chaplain bankruptcy attorney Harrisonburg VA

Harrisonburg Office

1951 Evelyn Byrd Ave., Ste E, Harrisonburg, VA 22801

Articles & Speaking Engagements.

Chapter 4: Property of the Bankruptcy Estate in Bankruptcy Practice in Virginia (5th ed., 2025) (with Hannah W. Hutman).
Yellow Corp. and the Calculation of Withdrawal Liability, Am. Bankr. Inst. L.J. June 2025, at 22 (with Ian Roberts).
A Practical Approach to Using Bankruptcy Rules Effectively: Part 6: Rule 9024 – Relief from a Judgment or Order, NACTT Newsl., Mar. 17, 2025.
A Practical Approach to Using Bankruptcy Rules Effectively: Part 5: Rule 9023 – New Trial; Altering or Amending a Judgment, NACTT Newsl., Mar. 10, 2025.
Is Finality Always Worth the Wait?, Am. Bankr. Inst. L.J. Dec. 2024, at 36 (with Brittany B. Falabella).
Rules Are Made to Be Broken . . . if in Conflict with the Code, Am. Bankr. Inst. L.J. Nov. 2024, at 22 (with Vincent J. Roldan).
Hear Me Out: The Supreme Court Gives Voice to Parties in Interest, Am. Bankr. Inst. L.J. Aug. 2024, at 28 (with Brittany B. Falabella).
Discharge, Disclosure and Due Process: Bankruptcy’s Bargain, Am. Bankr. Inst. L.J. July 2024, at 30 (with Brandon Poirier).
Must the Sub V Debtor’s Debts Be Linked to Its Current Business?, Am. Bankr. Inst. L.J. Oct. 2023, at 26 (with David Cox).
Editor of The Best of ABI 2022: The Year in Consumer Bankruptcy (2023).
She Works Hard for the Money: The Chapter 13 Debtor’s Plight in Obtaining Credit, NACTT Quarterly, Jan.–Mar. 2023, at 8 (with Hon. Rebecca B. Connelly) (Cover Article).
No Good Deed Goes Unpunished as COVID Forbearances Come Due, Am. Bankr. Inst. L.J. Nov. 2022, at 26 (with M. Christine Maggard).
A “Cringeworthy,” Cautionary Tale: How the NRA Missed Its Shot at Chapter 11, Am. Bankr. Inst. L.J. Aug. 2021, at 12 (with Vincent J. Roldan) (Cover Article).
New Claim in Town: CARES Forbearance Claims under Section 501(f), Bankr. L. News (Va. State Bar, Bankr. L. Section), Spring 2021, at 6.
The Terminator Argument: The Duty of Competence in Using Artificial Intelligence, Am. Bankr. Inst. L.J. Nov. 2019, at 28 (with Nisha R. Patel).
Debtors Against the SSA: Who May Hear the Case?, Am. Bankr. Inst. L.J. Aug. 2019, at 14 (with Hon. Rebecca B. Connelly).
When Acting in Good Faith Isn’t Enough: A Taxing Decision for IRS, Am. Bankr. Inst. L.J. Sept. 2018, at 14 (with Hon. Elizabeth L. Gunn).
Star-Cross’d: The Tragedy of Chapter 13 and the Modern Student Loan Debtor, ABI Consumer Newsl., Nov. 16, 2018.
Repaying Your Student Loans, Part 1: Tax Considerations in Repayment, Credit Abuse Resistance Education Blog, Mar. 17, 2017, available at https://care4yourfuture.org/repaying-student-loans-pt1/.
Avoiding [via] the National Form Plan, ABI Consumer Newsl., Feb. 6, 2017.
Federal Rule Amendments Effective Dec. 1, 2015, ABI Consumer Newsl., Feb. 4, 2016.

National Association of Chapter 13 Trustee 61st Annual Seminar
July 10, 2026 (New York, NY)
Pre- and Post-Petition Causes of Action: Who Represents, Who Recovers, and Who Pays?
Twelfth Annual Western District of Virginia Bankruptcy Conference
May 30, 2026 (Roanoke, VA)
Alphabet Soup Litigation (FCRA, FDCPA, RESPA, and more)
Harrisonburg-Rockingham Bar Association Meeting CLE
April 8, 2026 (Harrisonburg, VA)
Deconstructing the Code: Spotlight on § 362
ABI Winter Leadership Conference
December 5, 2025 (Phoenix, AZ)
Deconstructing the Code: Spotlight on § 362
40th Annual Mid-Atlantic Institute on Bankruptcy and Reorganization Practice
September 25, 2025 (Charlottesville, VA)
Recent Developments for Advanced Bankruptcy Practitioners
Eleventh Annual Western District of Virginia Bankruptcy Conference
May 30, 2025 (Roanoke, VA)
Recent Developments
Virginia State Bar Annual Bankruptcy Practice Seminar
March 14, 2025 (Richmond, VA)
A Heavy Lift: The Mechanics of Relief from Stay Actions
American Bankruptcy Institute’s Consumer Practice Extravaganza (CPEX)
January 22, 2025 (Webinar)
Consumer Rules Update
The Academy, National Association of Chapter 13 Trustees
January 7, 2025 (Webinar)
Where in the Rules Does It Say . . . ?
The Academy, National Association of Chapter 13 Trustees
October 17, 2024 (Webinar)
Where in the Code Does It Say . . . ?
39th Annual Mid-Atlantic Institute on Bankruptcy and Reorganization Practice
September 26, 2024 (Charlottesville, VA)
Recent Developments for Advanced Bankruptcy Practitioners
ABI Southeast Bankruptcy Workshop
July 27, 2024 (Naples, FL)
Using Bankruptcy Rules Effectively: Tips and Traps
Virginia State Bar Annual Bankruptcy Practice Seminar
March 8, 2024 (Richmond, VA)
Recent Developments in Virginia Bankruptcy Practice
ABI Midwestern Bankruptcy Institute
October 19, 2023 (Kansas City, MO)
Consumer Panel: Student Loan Topics
Hudson Valley Bankruptcy Bar Association, 20th Annual New Deal for Consumer Bankruptcy Seminar
September 23, 2023 (Poughkeepsie, NY)
Discharging Student Loan Debt: Department Guidance and Completing the Attestation
ABI Mid-Atlantic Bankruptcy Workshop
August 9, 2023 (Bedford, PA)
Hot Topics in Subchapter V
TMA/IWIRC Virtual Event
June 2, 2023 (Webinar)
Bankruptcy Judges Panel (Moderator)
Richmond Bar Association CLE
January 24, 2023 (Webinar)
The Western Way: Perils, Pitfalls, Possibilities, and Procedures
American Bankruptcy Institute’s Consumer Practice Extravaganza (CPEX)
November 18, 2022 (Webinar)
How to Bring a § 523(a)(8) Claim
Fifth Annual Western District of Virginia Bankruptcy Conference
June 1, 2018 (Roanoke, VA)
Staff Breakout Session: Chambers Staff Panel
Fourth Annual Western District of Virginia Bankruptcy Conference
June 2, 2017 (Roanoke, VA)
Bankruptcy Judges Panel: Rules, Reminders, and Requests
Staff Breakout Session: Dealing with Chambers
Third Annual Western District of Virginia Bankruptcy Conference
May 6, 2016 (Roanoke, VA)
Bankruptcy Judges Panel: Case Law, Amended Rules, and New Procedures
Second Annual Western District of Virginia Bankruptcy Conference
April 30, 2015 (Roanoke, VA)
Court’s Clerks’ Commentary: Orders; Chambers Procedures; Rule 7055; Rule 7026; Opinion Libraries

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