An increasing number of automation technologies for dairy cattle farming, including automatic milking, feeding, manure removal and bedding, are now commercially available. The effects of these technologies on individual aspects of animal welfare have already been explored to some extent. However, as of now, there are no studies that analyze the impact of increasing farm automation through various combinations of these technologies. The objective of this study was to examine potential correlations between welfare indicators from the Welfare Quality^® Assessment protocol and dairy farms with varying degrees of automation. To achieve this, 32 trial farms in Northern and Central Germany were categorized into varying automation levels using a newly developed classification system. The Welfare Quality^® Assessment protocol was used to conduct welfare assessments on all participating farms. Using analysis of variance (ANOVA), overall welfare scores and individual measures from the protocol were compared across farms with differing automation levels. No significant differences were observed in overall welfare scores, suggesting that the impact of automation does not exceed other farm-related factors influencing animal wellbeing, such as housing environment or management methods. However, significant effects of milking, feeding, and bedding systems on the appropriate behavior of cattle were observed. Higher levels of automation had a positive impact on the human–animal relationship and led to positive emotional states. Moreover, farms with higher automation levels had significantly lower scores for the prevalence of severe lameness and dirtiness of lower legs. It could be concluded that a higher degree of automation could help to improve animal welfare on dairy farms.