The Back Door to Termination

How Return to Office Mandates Can Become Constructive Discharge and Disability Discrimination

“You can’t eat the orange and throw the peel away — a man is not a piece of fruit!” — Willy Loman, in Arthur Miller’s Death of a Salesman (1949)

The Mandate That Isn’t Really About the Office

Willy Loman spent thirty-four years giving his best to a company that, in the end, had no more use for him. Arthur Miller wrote that line for a traveling salesman in 1949, but he could just as easily have been writing it for the employee who gets an email in 2026 announcing that everyone is required back in the building five days a week — including the employee who was hired specifically to work from home, the employee who moved two states away in reliance on that promise, or the employee who has a documented medical condition that made remote work necessary in the first place.

These sudden reversals of previously granted or medically documented work from home accommodations can completely change the nature and character of one’s job. It can make a formerly possible job impossible, and a formerly desirable position untenable. For those workers who have experienced the sudden removal of medically necessary work from home arrangements, the consequences can be devastating.

Most return-to-office mandates are exactly what they say they are: a business decision about how a company wants its people to work. But a growing number of them are something else entirely — a quiet, deniable way of pushing specific people out the door without paying severance, without triggering unemployment claims, and without ever having to say the word “fired.”

This article explains, in plain language, when a return-to-office mandate crosses the line from a legitimate management decision into something the law calls “constructive discharge,” and when a denial of a remote-work accommodation crosses into disability discrimination.

We represent employees around the nation but we will focus the lens in this article on the jurisdictions of Connecticut and New York — but we will tell you honestly where the law protects employers, too.

Why This Is Happening Right Now

According to a widely cited 2025 survey from Resume.org, roughly a third of employers said they intended to follow the lead of companies like Amazon and require employees back in the office five days a week. That is a lot of households suddenly facing a decision that has nothing to do with whether they can still do their jobs well, and everything to do with whether they can still show up to a building at all.

Here is the uncomfortable financial logic behind some of these mandates: a resignation costs an employer almost nothing. There is no severance check to write, no unemployment insurance claim to fight, and none of the notice obligations that come with a formal layoff. If an employer wants certain people gone — an employee who took FMLA leave, an employee who complained about discrimination, an employee whose disability requires flexibility — announcing a rigid in-office requirement and waiting for that person to quit can look, on paper, like nothing happened at all.

The law does not see it that way. Two separate legal theories come into play here, and it is worth understanding both, because they protect different things and require different proof.

Theory One: Constructive Discharge — When Quitting Is Legally the Same as Being Fired

“Constructive discharge” is the legal term for a simple idea: if your employer makes your working conditions so intolerable that a reasonable person in your position would feel they had no choice but to quit, the law treats your resignation as if you had been fired. You do not lose your discrimination or retaliation claim just because you were the one who typed the resignation letter.

The United States Supreme Court set out this standard in Pennsylvania State Police v. Suders. To win a constructive discharge claim, you generally have to show two things: that your employer created working conditions that were genuinely intolerable — not just unpleasant or frustrating, but intolerable — and that you actually resigned because of them.

A separate Supreme Court decision, Green v. Brennan, dealt with timing rather than the merits of the claim. The Court held that the clock for filing a claim starts running on the day you give notice that you are resigning — not on the day the bad conditions began, and not on your last day of work. This matters in practice: if you are considering resigning over an RTO mandate, the deadline to act may be running from the moment you say “I quit,” so this is exactly the kind of decision to make with a lawyer before you make it, not after.

What does this mean for a return-to-office mandate specifically? An RTO announcement alone — even an unwelcome, inconvenient one — is unlikely by itself to meet the “intolerable” standard. Courts do not consider it intolerable simply because a policy you dislike was put in place. What changes the analysis is context: Was the mandate announced right after you took medical leave, filed a complaint, or asked for an accommodation? Were you specifically hired, in writing, for a remote position, and is the company now reneging on that promise for you in particular while others keep their arrangements? Did you raise the problem with your employer and give them a real chance to work something out before you resigned?

That last point matters more than most people realize. Courts generally want to see that you gave your employer a fair opportunity to fix the situation before you walked away. Quitting the same day the mandate is announced, without ever raising your specific circumstances, can make a constructive discharge claim harder to prove — not because your frustration isn’t legitimate, but because the law wants employers to have a chance to respond first.

Theory Two: Disability Discrimination — When Remote Work Is a Medical Necessity, Not a Preference

The second, and often stronger, legal theory applies when an employee has a medical condition that remote work accommodates. Under the Americans with Disabilities Act (ADA), and under Connecticut’s and New York’s own disability discrimination laws, an employer generally has to provide a “reasonable accommodation” to a qualified employee with a disability — unless doing so would cause the employer genuine, significant difficulty.

A Major Win for Employees: Tudor v. Whitehall Central School District

In March 2025, the U.S. Court of Appeals for the Second Circuit — the federal appeals court that governs Connecticut and New York — issued a decision that meaningfully strengthened accommodation rights. In Tudor v. Whitehall Central School District, a teacher with PTSD had received a short daily break as an accommodation for years, until the school district cut it off. The lower court had ruled against her, reasoning that because she could still technically do her job without the break, she wasn’t entitled to it as a matter of law. The Second Circuit reversed, holding squarely that an employee may still be entitled to a reasonable accommodation even if she is capable of performing her job without it.

That may sound technical, but its effect on return-to-office cases is significant. Employers can no longer defend a decision to deny remote work simply by arguing, “Well, they could have come into the office if they really had to.” That argument, standing alone, is no longer enough in Connecticut, New York, or Vermont, all of which fall under the Second Circuit’s authority.

The Other Side: Castelino v. Whitman, Breed, Abbott & Morgan

Employees should also understand the limits. In Castelino v. Whitman, Breed, Abbott & Morgan, LLC, decided by the Connecticut Appellate Court in 2025, a legal assistant with diabetes and asthma asked to work fully remotely during the pandemic. Her employer said no, because her job required tasks that could only be done in person — maintaining physical client files, scanning documents, and obtaining original signatures and notarizations for real estate closings. The Connecticut Appellate Court sided with the employer, holding that in-person attendance was, on these facts, an essential part of her specific job, and that eliminating it entirely was not a reasonable accommodation.

Castelino is a useful reality check. Not every job can be done from a laptop at the kitchen table, and the law does not require an employer to eliminate the core duties of a position just because an employee would prefer to work from home. The lesson for employees is this: your case is strongest when your actual job duties can be performed remotely, and weakest when your employer can point to specific, genuine tasks that require your physical presence.

What Other States Are Saying — Not Binding Here, But Worth Knowing

A note on how to read what follows: the cases below come from courts outside Connecticut and New York. They are not binding on courts here — a Connecticut or New York judge is not required to follow them. But judges often look to how other federal courts are handling the same fact patterns, so these decisions are useful “persuasive authority” even though they are not the law of this state.

The U.S. Court of Appeals for the Fifth Circuit, which covers Texas, Louisiana, and Mississippi, ruled against an employee in Hayes v. GStek, Inc. in May 2026. The employee, an IT systems administrator, had been diagnosed with autism, major depressive disorder, and social anxiety disorder after returning to in-person work post-pandemic, and asked to work from home full time. His employer offered a compromise of two to three remote days per week instead. The Fifth Circuit sided with the employer, reasoning that in-person attendance is presumed to be an essential function of most jobs, and that a partial accommodation that actually works can satisfy the ADA even if it isn’t the exact accommodation the employee wanted.

These cases are a reminder that courts nationally are generally skeptical of a demand for full-time, indefinite remote work — as opposed to a specific, medically necessary adjustment — particularly once the pandemic-era justification for blanket remote arrangements has passed.

Put together, the emerging national trend — including in courts that do not bind Connecticut or New York — draws a real distinction between an employee who needs a specific, targeted accommodation tied to a documented medical condition, and an employee who simply prefers not to commute. The former has a real legal claim. The latter, standing alone, generally does not.

Connecticut’s Extra Layer of Protection: CFEPA

Connecticut employees have a second source of protection beyond the federal ADA: the Connecticut Fair Employment Practices Act, or CFEPA. This matters enormously for anyone working at a small company. The federal ADA only applies to employers with fifteen or more employees. CFEPA, as amended effective October 1, 2022, applies to employers with as few as one employee. If you work for a small Connecticut business and assumed federal law didn’t protect you because your employer is too small, CFEPA may still cover you.

Connecticut courts generally look to the same body of ADA case law when interpreting CFEPA’s disability protections, so everything discussed above about Tudor and Castelino applies with equal force to a CFEPA claim. If you believe you have been discriminated against, a complaint with Connecticut’s Commission on Human Rights and Opportunities (CHRO) generally must be filed within 300 days of the discriminatory act — so do not wait to get advice.

New York: Timing Is Everything

New York is an at-will employment state, which means that, standing alone, an employer is generally free to require employees to work from the office. Most return-to-office mandates in New York are perfectly legal.

What changes that analysis is timing. If your employer’s RTO announcement lands shortly after you filed a discrimination complaint, took FMLA or New York Paid Family Leave, or requested a disability accommodation, that timing can be powerful circumstantial evidence of retaliation — evidence that the mandate wasn’t really about business needs at all, but about you specifically. And because New York falls within the Second Circuit, the Tudor decision discussed above governs ADA accommodation claims here exactly as it does in Connecticut.

The Finer Points – How Do Courts Rule On These Cases In Practice?

1. A remote arrangement may be reasonable where the employee can perform the real job remotely.

In Mosby-Meachem v. Memphis Light, Gas & Water Division, the Sixth Circuit upheld a jury verdict for an in-house attorney denied a ten-week, temporary work-from-home accommodation during medically required bedrest.

The employer argued that physical presence was essential because the attorney’s job description listed litigation, depositions, and employee supervision. The court held that the jury could reject that characterization because the evidence showed:

she had successfully worked remotely before;
colleagues and outside counsel believed she could handle her work from home;
she had not actually tried cases or taken depositions during her years in the role;
the written description did not necessarily reflect the work she actually performed; and
the requested arrangement was finite, not indefinite.

A broad job description is not conclusive. The relevant question is whether the employee’s actual responsibilities during the requested period could be performed remotely.

2. Remote work can be reasonable when physical presence is not itself an actual essential function.

In Humphrey v. Memorial Hospitals Association, the Ninth Circuit reversed summary judgment for the employer. A medical transcriptionist with OCD sought work from home after a flexible-start arrangement failed.

The court concluded there was a triable issue because:

the employer already allowed some transcriptionists to work from home;
the employee’s transcription quality and productivity were strong;
her disability interfered principally with leaving home and arriving at the facility, rather than with doing the transcription itself; and
being physically at the employer’s office was not shown to be an essential function of the transcriptionist role.

The employer could not rely on disability-related attendance discipline to reject an otherwise feasible accommodation. If the disability affects the commute or ability to enter a particular workplace—not the ability to complete the work—telework may directly address the limitation. A policy that disqualifies employees with disability-caused attendance problems from telework can be legally vulnerable.

3. A blanket “managers must be in the building” rule is weak where the employee demonstrated effective remote performance.

In Peeples v. Clinical Support Options, Inc., the District Court in Massachusetts granted preliminary injunctive relief requiring temporary telework for an assistant manager with asthma during the COVID-19 pandemic.

The plaintiff had performed all essential duties remotely for approximately four months. The employer denied continued telework based on a general policy requiring managers onsite, despite the employee’s supervisor supporting the request and other managers remaining onsite. The court found a substantial likelihood that the employer had not conducted an individualized inquiry or shown that continued telework would cause undue hardship. “All managers must return” is not, standing alone, an individualized accommodation analysis. Employers should be prepared to explain which functions require the particular employee’s physical presence and why coverage by other onsite managers does not suffice.

4. Successful long-term remote work creates a triable issue of fact.

In Harter v. Franklin County Board of Commissioners, (No. 2:23-cv-2995) S.D. Ohio, Aug. 19, 2025) the District Court for the Southern District of Ohio held that triable issues of fact existed preventing summary judgment against the plaintiff. The plaintiff, a finance administrator, worked 100% remotely for more than a year under a medical arrangement. Her supervisor’s contemporaneous review stated that she remained an active team member, was available by phone and video, and met or exceeded expectations. After the employer adopted a policy ordinarily limiting telework to 40%, it denied her request to continue full-time remote work and required at least 60% in-office attendance.

The court denied summary judgment to both sides because a jury could find that:

the employee’s successful remote performance and favorable contemporaneous review showed she could perform the essential functions remotely;
the employer’s later, litigation-era affidavits alleging productivity, oversight, and supervisory problems conflicted with the contemporaneous record;
the job description did not itself require in-person work; and
the employer had not adequately explained why its 60% in-office threshold was essential for this employee’s actual duties.

This case strongly supports the proposition that a sudden RTO policy cannot defeat an accommodation claim merely because the employer announces a percentage-of-time office requirement. The employer must explain why the specified onsite presence is tied to essential duties.

5. Does years of successful remote work prove that in-office attendance is no longer essential?

No—but it is powerful evidence. A successful remote-work history does not permanently eliminate an employer’s ability to require in-person work. But it can be substantial evidence that the employee can perform the job’s actual essential functions remotely, particularly where contemporaneous performance reviews, productivity data, communication records, and the employer’s own prior accommodation decisions show that the arrangement worked.

Courts typically ask the following:

What did the employee actually do remotely?
Were the central duties performed, deadlines met, clients served, and work product delivered?
What did contemporaneous evidence show?
Positive evaluations, productivity reports, lack of corrective action, successful audits, normal response times, and praise from supervisors are more persuasive than later litigation affidavits.
Which asserted duties genuinely require onsite presence?
A claim that “collaboration,” “culture,” “visibility,” or “supervision” is better in person may be insufficient unless supported by specific job-related evidence.
Can the occasional in-person task be handled through a tailored arrangement?
A hybrid schedule, periodic onsite visits, remote supervision, reassignment of marginal tasks, or advance scheduling may preserve the essential functions without demanding five days in the office.
Has the job actually changed?
A real operational change can alter the essential-functions analysis. But a mere change in management preference, culture, or generalized RTO policy should not be treated as self-proving.
Why can an employer nevertheless prevail after years of remote work prove the in-office work is non-essential?

The leading cautionary authority is Bilinsky v. American Airlines, Inc. American Airlines had allowed an employee with multiple sclerosis to work from Chicago for years. After a merger, however, the employee’s department shifted from principally written communications to live events, crisis management, and rapid onsite coordination. The company required all similarly situated remote employees—not only the plaintiff—to work at headquarters. The court held that the employer could end the remote arrangement because evidence showed that the job’s actual essential functions had changed.

That case supports two important points:

Successful telework does not freeze a job forever. An employer may show a genuine, nondiscriminatory change in responsibilities that makes onsite work essential.
But the employer needs evidence of a real change—new work, new responsibilities, concrete onsite demands, and a consistent policy—not simply the assertion that it now values physical presence more than before.

The Seventh Circuit later framed the post-pandemic analysis similarly. In Kinney v. St. Mary’s Health, Inc., the court explained that pandemic remote work does not automatically establish that onsite work is nonessential in the long term. But it also rejected categorical presumptions against telework and emphasized a specific inquiry into the employee’s job and the particular duties that must be performed in person.

What You Should Actually Do

Do not resign the day the mandate is announced. However justified your frustration, a hasty resignation can weaken a constructive discharge claim. Give your employer a real, documented opportunity to address your situation first.
Put your accommodation request in writing, and be specific about the medical need behind it — not just a general preference to stay remote.
Save everything: the RTO announcement itself, your original hiring documents or offer letter (especially if you were hired as a remote employee), your performance reviews, and the timeline connecting the mandate to any leave, complaint, or accommodation request you made.
If your employer denies your accommodation request, ask for the reasoning in writing. A vague, unexplained “no” is a red flag, not a legal defense.
Talk to an employment lawyer before you resign, not after. Whether you have a constructive discharge claim, a disability discrimination claim, both, or neither depends heavily on facts specific to your situation — and, as Green v. Brennan makes clear, the clock may already be running the moment you announce you’re leaving.

Conclusion: You May Be Asked to Come Back. You May Not Be Pushed Out.

An employer is generally allowed to decide how and where its work gets done, and that authority deserves real respect — Castelino and Hayes are useful reminders that not every remote-work preference is a legal entitlement. But that authority has limits. When a return-to-office mandate is really a tool to force out a specific employee — because of a disability, a complaint, or a leave they took — the law in Connecticut and New York does not let the label “business decision” make that lawful.

Willy Loman never got the chance to ask the law for anything; his story ends the way it does precisely because the law he needed didn’t yet exist. Today, an employee who is quietly being squeezed out through an inflexible mandate has real legal tools — constructive discharge and disability discrimination law chief among them. The point of both is the same: you can be asked to come back to the office. You cannot be forced out the back door because of who you are or what medical accommodations you needed.

If a Return-to-Office Mandate Has Put Your Job on the Line

If your employer has issued a return-to-office mandate that conflicts with a medical need, a documented remote-work agreement, or came suspiciously soon after you took leave or filed a complaint, you may have legal options — no matter what state you work in. Contact Carey & Associates, P.C. to discuss your situation with an experienced employment attorney. We represent employees throughout Connecticut and New York in constructive discharge, disability discrimination, and retaliation matters. Reach us at www.capclaw.com or call (203) 255-4150.