This study compared the use of anatomical glass fiber posts using bulk-fill composite resin with computer-aided design and computer-aided manufacturing (CAD/CAM) milled glass fiber post in oversized root canals, through bond strength (BS) and fracture resistance (FR) tests (fracture load). A total of 48 mandibular premolars were selected, half of them had their crowns removed at the cemento-enamel junction (CEJ) and the other half were sectioned 2 mm above the CEJ. Subsequently, teeth were endodontically treated. After 1 week, the standard preparation of the canals was carried out, and the roots were divided into three groups (n=16), according to the use of different restorative techniques (control: prefabricated glass fiber post [PFP], direct anatomical glass fiber post [AFP], and CAD/CAM milled glass fiber post [MFP]). After luting procedures using Single Bond Universal and RelyX Ultimate (3M ESPE), for eight teeth in each group, six specimens were obtained (two slices from each root third: cervical, middle, and apical). For the remaining eight roots of each group, standardized preparations for metal-free crowns, milling of 5 mol% yttria-stabilized tetragonal zirconia polycrystalline, cementation of the crowns, and periodontal ligament simulation were performed. Then, for each group, the BS was evaluated through the push-out test, and the FR was evaluated in compression. The data obtained from BS were submitted to two-way analysis of variance (ANOVA; group vs root region) and Tukey (α=0.05) and from FR to one-way ANOVA (group) and Tukey (α=0.05). For the BS test, the MFP group was statistically superior to the PFP group in all root regions and was statistically superior to the AFP group only in the cervical region, being statistically similar in the middle and apical root regions. For the FR test, the MFP group was statistically superior to the PFP and AFP groups. The milled fiber post technique can be a legitimate alternative in the restoration of weakened roots with flared root canals.