Background: This study aimed to evaluate the impact of image enhancement techniques on the interobserver reliability of tear break-up time (TBUT), tear meniscus height (TMH), corneal fluorescein staining (CFS) scoring, and conjunctivochalasis detection using the Smart Eye Camera (SEC), a portable device for anterior segment examination. Methods: A retrospective analysis was conducted on video recordings captured by the SEC from 46 patients with dry eye disease (DED). Separate sets of images were created for each level of enhancement: unenhanced (G0), mildly enhanced (G3), and strongly enhanced (G7). These sets were not intermixed, ensuring that each enhancement level was assessed independently. Three observers—two DED specialists and one general ophthalmologist—assessed TBUT, TMH, CFS scores, and conjunctivochalasis. Interobserver reliability was evaluated using intraclass correlation coefficients (ICCs) for each image set. Results: Interobserver reliability for CFS scores significantly improved with G3, yielding an ICC of 0.8413. In contrast, G7 improved reliability for TBUT measurements (ICC = 0.7381), but led to a notable decrease in reliability for both CFS scoring (ICC = 0.2259) and conjunctivochalasis detection (ICC = 0.0786). Furthermore, the assessment of TMH demonstrated a progressive decline in accuracy with increasing levels of image enhancement. Conclusions: Image enhancement using the SEC improved the diagnostic consistency of dry eye specialists and general ophthalmologists, especially for TBUT and CFS assessments. However, excessive enhancement may obscure key diagnostic features, indicating the need for careful optimization of image processing techniques depending on the diagnostic focus.