(1) Background: Cementation of glass fiber posts to root canals has been associated with various failures, especially debonding. This narrative review aims to present the contemporary concepts concerning the adhesive cementation of glass fiber post and to discuss the optimal management of these factors. (2) Methods: Electronic search was performed in MEDLINE/Pub Med and Google Scholar using selected keywords examining the parameters post length, surface treatment of glass fiber posts, post space preparation and dentin pretreatment, resin cement selection, adhesive systems and hybrid layer formation, and clinical techniques. (3) Results: The search led to the selection of 44 articles. Epoxy resin-based endodontic sealers are recommended and the use of temporary cement in the root canal should be avoided. The minimum length of a glass fiber post adhesively cemented to a root canal is 5 mm. Irrigating the root canals with chlorhexidine, MTAD, or EDTA (alone or in combination with NaOCl) after post space preparation seems to enhance the bond strength. Silane application on the surface of the post seems to be beneficial. Concerning resin cements and adhesive systems, the results were rather inconclusive. Finally, resin cement should be applied inside the root canal with an elongation tip and photoactivation should be delayed. (4) Conclusions: Contemporary concepts of adhesive cementation of glass fiber posts can indeed improve the bond between glass fiber posts, resin cement, and root canal dentin, however, evidence coming from long-term randomized prospective clinical trials is needed in order to obtain safer conclusions.