Employers continue to face challenges managing employee requests for additional or extended medical leaves of absence for employees who are not eligible for or have exhausted FMLA leave. The Equal Employment Opportunity Commission (“EEOC”) and many federal courts have found that unpaid leave may be a form of reasonable accommodation under the Americans with Disabilities Act (“ADA”) even when FMLA leave is not available if the employee will likely be able to perform the essential functions of his or her position upon return. Because employee leaves and accommodation requests are fact specific and analyzed on a case-by-case basis, courts have been reluctant to place definitive limits on the length of employee leaves as reasonable accommodations. As a result, employers are often uncertain on whether an additional or extended leave of absence request must be granted and when they can finally say “enough is enough.”