Drive‐by structural health monitoring (SHM) is a cost‐efficient alternative to the direct SHM of short‐ to medium‐size bridges requiring no sensors to be installed on the structure. However, drive‐by SHM is generally known as a short‐term monitoring technique due to the challenges associated with using multiple passages of instrumented vehicles for a long time. This paper proposes combining the potentiality of connected and autonomous vehicles (CAVs) into drive‐by damage detection by introducing In‐Fleet SHM. To the authors’ knowledge, this is the first study that proposes using CAVs for SHM application in civil engineering structures. Each In‐Fleet CAV could automatically collect the vehicle's persistent and temporal data by the embedded sensors and transmit them to edge computing systems for analysis. These persistent data include type and model and temporal parameters encompassing position, speed, heading, and vertical acceleration of CAVs. Knowing the persistent and temporal data of the passing vehicles over the transportation infrastructures enables the identification of the dynamic parameters of the bridge from the vehicles’ vertical acceleration response using drive‐by techniques and, on the other hand, reconstruction of the finite element model of the passing vehicles over the supporting bridges in a near real‐time manner. In contrast to the drive‐by SHM, In‐Fleet monitoring has an expanded spatial and temporal coverage, enabling continuous near real‐time monitoring of highway bridges of the transportation network. The accuracy and resolution of the identified modal components in In‐Fleet SHM are enhanced due to the crowdsensing nature of the collected data. Furthermore, by offering a unique set of characteristics, this method fills the crucial gap in implementing Industry 4.0 technologies and digital twins for SHM of bridges.