Optical fiber measurement systems have recently gained popularity following a multitude of intensive investigations. A new technique has been developed for these measurement systems that uses Rayleigh backscatter to determine the distributed strain measurement over the total length of a fiber. These measurement systems have great potential in civil engineering and structural health monitoring. This paper addresses some preliminary comparisons between three different fiber coatings and six different adhesives on steel structures. The results are based on a bending test with specimens made of precision flat steel; optical fiber strain measurements were compared with photogrammetric strain measurements. Analysis of the test data showed a strong correlation between the optical measurement system’s results and the theoretical results up to the yielding point of the steel. Furthermore, the results indicate that fibers with the Ormocer® and polyimide coatings have almost no loss in the strain measurements. The main results of this investigation are a guideline describing how to attach optical fibers to steel surfaces for distributed fiber optical strain measurements and recommendations for coatings to obtain realistic strain values. Additionally, the advantages of distributed strain measurements were revealed, which illustrates the potential of Rayleigh backscattering applications.