Background: Dysphagia assessment in postacute stroke patients can decrease the incidence of complications like malnutrition, dehydration, and aspiration pneumonia. It also helps to avoid unnecessary diet restrictions. The aim of this study is to verify if regular reassessment of dysphagia would change the diet management of postacute stroke patients in rehabilitation settings. Methods: This single-center retrospective study included 63 patients referred to an inpatient neurological rehabilitation center between 2018–2019. A standardized clinical swallowing evaluation and Fiberoptic Endoscopic Evaluation of Swallowing (FEES) were performed. Diet level according to Functional Oral Intake Scale (FOIS) was evaluated. As the primary endpoint, the FOIS values based on diagnostic procedures were assessed at hospital discharge, rehabilitation admission, and after FEES. Results: 19 women (30%) and 44 men (70%), with a mean age of 75 y (SD ± 10.08), were enrolled. The intergroup ANOVA revealed significant differences (p < 0.001) between dietary prescriptions in an acute care setting and following clinical and endoscopic reassessment in the rehabilitation center. Diet recommendations changed in 41 of 63 (65%) enrolled patients (p < 0.001). Conclusion: Instrumental diagnostic by FEES during the early convalescence period of stroke patients leads to clinically relevant changes to diet restrictions and lower rates of pneumonia. Our findings underline the need for regular and qualitative dysphagia diagnostics in stroke patients participating in neurological rehabilitation.