Composite materials, having better properties than traditional materials, are susceptible to potential damage during operating conditions, and this issue is usually not found until it is too late. Thus, it is important to identify when cracks occur within a structure, to avoid catastrophic failure. The objective of this chapter is to fabricate a new generation of strain sensors in the form of a wire/thread that can be incorporated into a material to detect damage before they become fatal. This microscale strain sensor consists of flexible, untwisted nylon yarn coated with a thin layer of silver using electroless plating process. The electromechanical response of this sensor wire was tested experimentally using tensile loading and then verified numerically with good agreement in results. This flexible strain sensor was then incorporated into a composite specimen to demonstrate the detection of damage initiation before the deformation of structure becomes fatal. The specimens were tested mechanically in a standard tensometer machine, while the electrical response was recorded. The results were very encouraging, and the signal from the sensor was correlated perfectly with the mechanical behavior of the specimen. This showed that these flexible strain sensors can be used for in situ structural health monitoring (SHM) and real-time damage detection applications.