Introduction
The most damaging effect of bad decisions is not always the immediate harm they cause. More often, it is the explicit blessing they bestow upon practices that should never have been dignified with judicial approval. When a federal judge cloaks misconduct in the robes of procedure, or validates inequities with the seal of precedent, the damage ripples outward. Bad decisions do not simply dispose of individual cases; they legitimize entire categories of abuse.
This dynamic was on full display in Prudential Insurance Co. of America v. Kowalski, where Judge Victor Bolden’s rulings transformed serious discovery abuses into normalized practice. The defendant, Jennifer Kowalski, my daughter, litigated the case pro se. She was not only disadvantaged by her lack of counsel but ultimately confined for refusing to surrender her personal passwords—despite mounting evidence that Prudential had already intruded deeply into her computer systems.
I. Background: Discovery Abuses and “Inadvertent” Production
From the outset, Prudential engaged in unilateral, overbroad, and unvalidated e-discovery practices. Its searches extended far beyond the scope authorized by the court, resulting in the wholesale capture of Kowalski’s personal accounts and devices.¹ Even Prudential’s own counsel admitted on the record that the company had “inadvertently produced” sensitive data during its forensic examination.²
For Kowalski, these were not abstract violations. She discovered that text files produced to her contained complete copies of documents from her private sources—including Facebook, LinkedIn, Microsoft, TD Bank, and other personal accounts.³ A third-party forensic affidavit confirmed that Prudential’s agents had embedded themselves in her computer’s operating system, demonstrating the extent of the intrusion.⁴
Despite these revelations, Prudential pressed forward. Rather than correct its conduct, the company designated over 1.8 million files—including non-confidential and irrelevant material—as “Attorney’s Eyes Only,” effectively depriving Kowalski of access to her own information.⁵ Prudential continued to demand her passwords, despite already having obtained expansive and unauthorized access to her systems.
II. Judicial Response: Confinement as Compliance
Faced with Prudential’s misconduct, Kowalski refused to provide her passwords. Her refusal was not obstructionist but conscientious, rooted in an unwillingness to enable further intrusion by a party that had already abused its access.
Judge Bolden, however, chose not to address Prudential’s violations. Instead, he converted Kowalski’s refusal into grounds for punishment, ordering her civilly confined until she complied. This outcome stands in sharp contrast to courts that have exercised restraint in compelled-password disputes. In United States v. Kirschner, a federal court recognized that disclosure of a password is inherently testimonial, implicating significant privacy concerns.⁶ Similarly, in In re Grand Jury Subpoena Duces Tecum Dated March 25, 2011, the Eleventh Circuit held that compelling a suspect to decrypt files violated the Fifth Amendment’s prohibition against self-incrimination.⁷
By ignoring Prudential’s misconduct and punishing Kowalski, Bolden effectively sanctioned practices that other courts have rejected as corrosive to both fairness and liberty.
III. Due Process and the Limits of Civil Confinement
Kowalski’s civil confinement also raises serious due process concerns. Civil contempt sanctions are lawful only to the extent that they are coercive rather than punitive. In International Union, United Mine Workers of America v. Bagwell, the Supreme Court drew a clear line: civil contempt is permissible only when the contemnor “carries the keys of [her] prison in [her] own pocket.”⁸ If the confinement ceases to serve a coercive purpose—or if compliance is impossible—continued detention becomes punitive, triggering full criminal due process protections.
Here, Kowalski’s confinement was not designed to coerce compliance in a fair discovery process; it was used to break her will after Prudential had already gained unauthorized access to her data. In such circumstances, the “keys to the prison” metaphor collapses. The sanction no longer served a legitimate coercive function but instead operated as punishment for principled resistance. This blurred the line between civil and criminal contempt, depriving Kowalski of the procedural protections she was constitutionally entitled to receive.
Courts have repeatedly warned that civil confinement must remain tightly tethered to due process. In Shillitani v. United States, the Supreme Court upheld confinement only because the contemnors could purge their contempt by testifying before a grand jury.⁹ But where compliance is unreasonable, indefinite, or sought in service of an abusive discovery process, civil confinement becomes constitutionally suspect. Bolden’s order crossed that boundary, transforming judicial coercion into judicial overreach.
IV. Implications: When Abuse Becomes Law
The consequences extend beyond Kowalski’s personal ordeal. When a federal judge endorses such conduct, the lessons reverberate. Corporations learn that invasive discovery can be excused as “inadvertent.” Courts learn that confinement may serve as a tool to compel compliance, even in the shadow of abuse. Citizens learn that standing on principle will not protect them but instead may result in the loss of liberty.
Other courts have warned against precisely this dynamic. In Crosmun v. Trustees of Fayetteville Technical Community College, the North Carolina Court of Appeals criticized procedures that gave requesting parties unilateral access to electronic evidence, noting that such practices violated producing-party privileges.¹⁰ Likewise, in American Home Assurance Co. v. Greater Omaha Packing Co., the court emphasized that producing parties must be afforded meaningful opportunity to contest e-discovery demands, recognizing the inherent dangers of one-sided control.¹¹
By disregarding these principles, Judge Bolden did not merely mishandle a single dispute—he endorsed a structural imbalance that undermines the fairness of discovery itself.
V. Policy Implications and Proposals for Reform
The lessons of Prudential v. Kowalski extend beyond its facts. They highlight systemic vulnerabilities in how courts approach compelled digital evidence, discovery management, and the treatment of pro se litigants. Several reforms are warranted:
Clearer Standards on Compelled Digital Evidence
Courts should adopt a presumption against compelled disclosure of passwords and encryption keys, recognizing that such disclosures are inherently testimonial. Statutory reform, akin to the Electronic Communications Privacy Act, could codify limits on judicial orders requiring decryption.
Stronger Protections for Producing Parties in E-Discovery
Discovery rules must reinforce the principle that producing parties—not requesting parties—control privilege designations. Amendments to Rule 26 could explicitly prohibit unilateral control of electronic sources by requesting parties, with sanctions for violations.
Judicial Training on E-Discovery Abuse
Federal judges should receive mandatory training on forensic technology and privacy implications, so that “inadvertent production” cannot be casually excused when it masks systemic intrusion.
Heightened Safeguards for Pro Se Litigants
Courts must adopt heightened scrutiny when a litigant proceeds without counsel, especially in technologically complex cases. Procedural protections—such as mandatory appointment of technical advisors or discovery monitors—could prevent imbalance from becoming abuse.
Reconsideration of Civil Confinement in Discovery Disputes
Congress or the Judicial Conference could issue guidance limiting civil contempt confinement to cases where the coercive purpose is clear and compliance is realistically attainable. Where discovery has already been compromised by misconduct, confinement should be off the table.
These reforms would not erase what happened in Prudential v. Kowalski, but they could prevent similar miscarriages from recurring.
Conclusion
The true legacy of Prudential v. Kowalski lies not only in the confinement of a pro se litigant who stood her ground, but in the dangerous blessing Judge Bolden conferred upon practices that should have been condemned. Bad decisions echo, and when they come from the federal bench, those echoes calcify into precedent.
In this case, the echo was unmistakable: intrusion forgiven, concealment tolerated, resistance punished. That is not justice. That is surrender.
Notes
Motion for Separate Evidentiary Hearing, Prudential Ins. Co. of Am. v. Kowalski, No. 3:21-cv-00541 (D. Conn. Feb. 27, 2023), ECF No. 265, at 2.
Id. at 3–4.
Affidavit of Defendant, Prudential v. Kowalski, No. 3:21-cv-00541 (D. Conn. Dec. 9, 2021), ECF No. 77-1 ¶ 65.
Id.
Motion for Separate Evidentiary Hearing, supra note 1, at 5–6.
United States v. Kirschner, 823 F. Supp. 2d 665, 669 (E.D. Mich. 2010).
In re Grand Jury Subpoena Duces Tecum Dated Mar. 25, 2011, 670 F.3d 1335, 1349 (11th Cir. 2012).
Int’l Union, United Mine Workers of Am. v. Bagwell, 512 U.S. 821, 828 (1994).
Shillitani v. United States, 384 U.S. 364, 371 (1966).
Crosmun v. Trustees of Fayetteville Tech. Cmty. Coll., No. COA18-1230, 2019 WL 355874, at *7 (N.C. Ct. App. Aug. 6, 2019).
Am. Home Assurance Co. v. Greater Omaha Packing Co., No. 8:11CV270, 2013 WL 4875997, at *4 (D. Neb. Sept. 11, 2013).
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