In a foster cow system, one or more calves are reared by a foster cow. With regard to the growing rejection towards the early separation of cow and calf after calving, such alternative rearing methods with prolonged cow–calf contact are coming more into focus. Nevertheless, there is a lack of recent studies investigating the effects of suckling multiple calves on the udder health of a foster cow. The present study aimed to initially describe the status and development of the udder condition and the microbial colonisation during the foster period. Thereby, the objectives were to determine whether suckling multiple calves was associated with an increase in intramammary infections (IMI) and a deterioration of udder constitution. A total of 99 Holstein Friesian foster cows from a large organic dairy farm in eastern Germany were included in this pilot study. Each foster cow was suckled by 3–4 calves and not additionally milked. Quarter milk samples were taken for cytomicrobiological examination at the beginning and end of the approximately 3.5 months suckling period. At the same time, the udders of 91 of these foster cows were clinically examined by visual assessment and manual palpation. In both the first and second examination (E1 and E2, respectively), Corynebacterium ssp. and non-aureus staphylococci (NaS) constituted the most frequently detected pathogen species in the 385 examined udder quarters. Classifying the quarters into mastitis categories was significantly different between the two examinations (p = 0.001). The number of quarters considered as healthy increased from E1 to E2 by 8.5%. At the same time, the number of quarters with mastitis decreased by 2.6%, the number of quarters with non-specific mastitis by 11.4% and the number of quarters with a latent infection increased by 5.4%. In total, 69.4% of the 121 infected udder quarters in E1 were bacteriologically cured in E2. A cytological cure was achieved in 28.1% of the 385 quarters. Both the bacteriological and cytological cure rate were spontaneous. A new infection occurred in 23.1% of the 385 examined udder quarters and was mainly attributable to infections with Corynebacterium spp. and NaS. During the suckling period, mainly new infections occurred and amounted to 73% in relation to presumed persistent infections (18.9%). The new infections were mainly attributable to infections with Corynebacterium spp. and NaS. Pasteurella spp. were also found in high percentages. A total of 10.1% of the quarters showed an increase in somatic cell count (SCC) above the threshold of 100,000 cells/mL from E1 to E2, indicating a new subclinical mastitis. Regarding udder condition, significant changes during the foster period were an increase in udder skin and teat lesions, a decrease in udder oedema, an increased amount of udder quarters with a consistency considered as normal and an increase in the number of udders showing no sign of udder cleft dermatitis. Moreover, teat length, circumference, and diameter increased significantly (p <, 0.05). In conclusion, there is a possibility that suckling multiple calves improves udder health in terms of mastitis but leads to an increased pathogen transmission at the same time, resulting in an increase in latent infections. Additionally, pathogens as Pasteurella spp., which are usually located in the upper respiratory system, could be detected in the mammary gland. The changes concerning the udder condition were manifold. However, it has not yet been conclusively clarified whether all these changes are exclusively due to calf suckling. Further investigations with a non-suckled control group are required.