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(1) Background: An ideal bond strength between endodontic posts and root canal dentin is essential for optimal retention and good prognosis. This study aimed to evaluate the push-out bond strength (PBS) of prefabricated fiber and metal posts, luted with resin cement to natural dentin. (2) Methods: Extracted premolars with similar root dimensions were assigned into two groups of 30 each for the metal and fiber posts. Teeth were mounted in acrylic blocks exposing 2 mm of the coronal root. Teeth were subjected to endodontic treatment and post-space preparations. Two groups were further subdivided into three sub-groups (n = 10) according to the size of the posts (# 4, 5 and 6). Posts were cemented with resin cement. Specimens were sectioned into 4 mm slices and subjected to the PBS test. (3) Results: The mean PBS was similar for the metal and fiber posts bonded with resin cement, showing a statistically significant result. An increase in post size increased the bond strength initially, but a further increase in size did not show any marked difference. A total of 71.66% of tested specimens failed with the adhesive failure mode. (4) Conclusions: Metal posts showed slightly higher retention compared to the fiber posts, although the p-value was similar for both types. An increase in the size of posts showed increased retention. The most common mode of failure was adhesive failure between cement and dentin. [ABSTRACT FROM AUTHOR]