Background: Pelvic floor muscle dysfunction (PFD) is common during pregnancy. To counteract pregnancy-associated PFD, women require sufficient knowledge and structured guidance on correct pelvic floor muscle (PFM) contraction to improve PFM perception and functional control. Identifying pregnant women who are unable to perform correct PFM contraction despite structured teaching may allow early referral for rehabilitative measures. Objective: At measurement stage 1, this study aims to investigate the influence of structured PFM teaching on pregnant women’s ability to perform targeted PFM contraction (tPFMC-A), assess PFM strength, and describe possible early PFD symptoms. Material and Methods: “pelviTrust” is a two-arm randomized, controlled longitudinal study and has been conducted in the Department of Midwifery Science, University of Tuebingen since February 2023. The study sample comprised 221 healthy pregnant women with singleton pregnancy at 18–22 weeks of gestation. The intervention group (IG; n = 113) (69 nulliparous, 40 primiparous and four biparous) completed the validated German Pelvic Floor Questionnaire for Pregnant and Postpartum Women (GPFQppw) and received individualized midwife-led teaching on PFM anatomy, functional activation and PFM-friendly behaviour, followed by visual inspection and vaginal palpation. Objective-targeted PFMC ability (tPFMC-A) and PFM strength (modified Oxford Scale) were compared with self-assessed ability. The control group (n = 101) (61 nulliparous, 38 primiparous, and two biparous) receives routine prenatal and postnatal care and completes the GPFQppw. The present analysis focuses exclusively on the IG at T1. Results: At T1, 88% of the 113 women in the IG believed they could contract their PFM, but only 68% demonstrated a correct tPFMC-A on visual inspection. Following structured teaching with individualized feedback, 97% achieved correct PFM contraction while 2.7% still had deficits. The median PFM strength was three on the modified Oxford Scale (interquartile range: 3–4). Stress urinary incontinence and flatulence were the most frequently reported symptoms. Primiparous and multiparous women reported urinary incontinence and descensus symptoms more often than nulliparous women (p < 0.001). Conclusions: At the first prenatal assessment, pregnant women often overestimate their ability to contract their PFM correctly. A structured, midwife-led PFM teaching improves objectively assessed PFM contraction ability and may be integrated into routine antenatal care to support PFM health in pregnant women.