This in vitro study aimed to evaluate the fracture resistance and mode of failure of endocrowns with proximal extension design compared to the conventional design, and to assess the agreement of evaluators on the failure mode. Twenty mandibular third molars free of caries with approximately similar root lengths and crown dimensions were sectioned parallel to the occlusal plane 2 mm above the cementoenamel junction (CEJ). Then, pulp chambers and canals were accessed, cleaned, and smoothed for the path of insertion. To achieve a symmetrical pulp chamber with an average depth of 3 mm, chambers were filled with flowable resin composite. Then, teeth were randomly divided into two groups (n = 10). The control group has all the walls at the same level. The test group had a box extension on the proximal wall 2 mm apical to the buccal and lingual wall level. Endocrowns (n = 20) of two different designs (conventional and proximal extensions) were fabricated using lithium disilicate (IPS e.max CAD, Ivoclar Vivadent, Schaan, Liechtenstein). After cementation, specimens were loaded with a round-end vertical loading tip at a rate of 0.5 mm per minute until fracture (INSTRON, Norwood, MA, USA). Then, the fractured specimens were collected for evaluation and assessment. Statistical analyses were performed using the Mann-Whitney U-test (α = 0.05) for fracture test analysis and Cohen’s Kappa for inter-rater reliability. The Mann-Whitney U-test showed a non-significant difference between the two groups (p = 0.142). However, the mode of failure of the endocrown with proximal extension showed more catastrophic failures than the conventional design. Adding proximal boxes to the endocrown design did not negatively impact the fracture resistance of the restoration. Visualization of the fracture line and tracing their apical end by direct vision or other diagnostic tools is an essential part of the evaluation of failures of endocrowns. Endodontically treated molar teeth with proximal caries extension might be restored with an endocrown with proximal extension. Clinicians should take extra care when visualizing the fracture lines and tracing their apical end as it might be very misleading.