Background/Objectives: Epiphora, or excessive tearing, is a common symptom often attributed to benign conditions such as dry eye or nasolacrimal duct obstruction. However, it can also be an early indicator of lacrimal sac tumors, which are frequently misdiagnosed or diagnosed late due to their subtle presentation. This study aims to identify the clinical features that contribute to delays and misdiagnoses of lacrimal sac tumors in patients presenting with epiphora, with the goal of improving early detection and treatment outcomes. Methods: This retrospective study reviewed medical records from Taipei Veterans General Hospital between 2007 and 2023, focusing on patients who presented with epiphora and were later diagnosed with pathologically confirmed lacrimal sac tumors. Inclusion criteria were limited to cases that were initially misdiagnosed or had a delayed diagnosis, with imaging and clinical evaluations confirming tumor-related tear drainage obstruction. Patients with non-tumor causes of epiphora were excluded. Results: Eleven cases of lacrimal sac tumors were identified, including two benign and nine malignant tumors. The average duration from symptom onset to diagnosis was 22.4 months. Common symptoms included epiphora (100%), discharge (54.5%), and hemolacria (18.2%). Subtle clinical signs, such as asymmetry in the medial canthal region and non-tender swelling, were frequently noted. Despite receiving appropriate surgical and adjuvant treatments, the impact of delayed diagnosis was significant. Two patients succumbed to tumor-related disease; one developed lung metastasis 12 years after diagnosis, and another experienced recurrence during a six-year follow-up after undergoing extensive exenteration, adjuvant chemotherapy, and radiotherapy. Conclusions: Lacrimal sac tumors can present insidiously with symptoms often mistaken for benign conditions, leading to significant diagnostic delays. Thorough history taking, meticulous physical examination, and timely imaging are crucial for early detection. Increased clinician awareness and a high index of suspicion for lacrimal sac tumors in patients with atypical epiphora are essential to improve prognosis and reduce the risk of severe outcomes.