Precise annotations for large medical image datasets can be time-consuming. Additionally, when dealing with volumetric regions of interest, it is typical to apply segmentation techniques on 2D slices, compromising important information for accurately segmenting 3D structures. This study presents a deep learning pipeline that simultaneously tackles both challenges. Firstly, to streamline the annotation process, we employ a semi-automatic segmentation approach using bounding boxes as masks, which is less time-consuming than pixel-level delineation. Subsequently, recursive self-training is utilized to enhance annotation quality. Finally, a 2.5D segmentation technique is adopted, wherein a slice of a volumetric image is segmented using a pseudo-RGB image. The pipeline was applied to segment the carotid artery tree in T1-weighted brain magnetic resonance images. Utilizing 42 volumetric non-contrast T1-weighted brain scans from four datasets, we delineated bounding boxes around the carotid arteries in the axial slices. Pseudo-RGB images were generated from these slices, and recursive segmentation was conducted using a Res-Unet-based neural network architecture. The model’s performance was tested on a separate dataset, with ground truth annotations provided by a radiologist. After recursive training, we achieved an Intersection over Union (IoU) score of (0.68 ± 0.08) on the unseen dataset, demonstrating commendable qualitative results.