We evaluated inter-examiner reliability in grading of clinical variables associated with meibomian gland dysfunction (MGD) in real-time examination versus a graded digital image. Meibography grading of meibomian gland atrophy and acini appearance, and slit-lamp grading of lid debris and telangiectasias were conducted on 410 post-menopausal women. Meibography and slit-lamp photos were captured digitally and saved for analysis by a masked examiner. Gland atrophy was graded as a proportion of partial glands in the lower lid, and acini appearance by the presence/absence of grape-like clusters. Lid debris and telangiectasias were graded based on severity and quantity from the same image, respectively. Observed agreement and weighted kappas (κ(w)) with 95% confidence intervals (CI) determined the degree of inter-examiner reliability between grading of these clinical variables in real-time examination and digital photographs using a multiple-point categorical scale. Observed agreement was determined for telangiectasias (40.6%), lid debris (50.9%), gland dropout (42.8%), and acini appearance (54.5%). Inter-examiner reliability for the four clinical outcomes ranged from fair agreement for acini appearance (κ(w) = 0.23, 95% CI = 0.14-0.32) and lid debris (κ(w) = 0.24, 0.16-0.32) to moderate agreement for gland dropout (κ(w) = 0.50, 0.40-0.59) and telangiectasias (κ(w) = 0.47, 0.39-0.55). Conclusions. Gland dropout and potentially lid telangiectasia grading from a photograph are more representative of grading in a real-time examination compared to acini appearance and lid debris. Alternative grading scales and/or clinical variables associated with MGD should be addressed in future studies.