Enhanced Recovery After Surgery (ERAS) protocols advocate early postoperative resumption of normal diet to decrease surgical stress and prevent excessive catabolism. The aim of the present study was to identify reasons for delayed tolerance of normal postoperative diet. This was a retrospective analysis including all consecutive colorectal surgical procedures since May 2011 until May 2017. Data was prospectively recorded by an institutional data manager in a dedicated database. Uni- and multivariate risk factors associated with delayed diet (beyond POD 2) were identified by multiple logistic regression among demographic, surgery- and modifiable pre- and intraoperative ERAS-related items. In a second step, univariate analysis was performed to compare surgical outcomes for patients with early vs. delayed oral intake. The study cohort consisted of 1301 consecutive colorectal ERAS patients. Herein, 691 patients (53%) were able to resume normal diet within two days of surgery according to ERAS protocol, while in 610 patients (47%), a delay in tolerance of normal diet was observed. Male gender was independently correlated to early tolerance (Odds Ratio (OR) 0.66; 95% Confidence Interval (CI) 0.46-0.84, p = 0.002), while ASA score ≥ 3 (OR 1.60; 95% CI 1.12-2.28, p = 0.010), abdominal drains (OR 1.80; 95% CI 1.10-2.49, p = 0.020), right colectomy (OR 1.64; 95% CI 1.08-2.49, p = 0.020) and Hartmann reversal (OR 2.61; 95% CI 1.32-5.18, p = 0.006) constituted risk factors for delayed tolerance of normal diet. Patients with delayed resumption of normal diet experienced more overall (Clavien grade I-V) (47% vs. 21%, p < 0.001) and major (Clavien grade IIIb-V) (11% vs. 4%, p < 0.001) complications and had a longer length of stay (9 ± 5 vs. 5 ± 4 days, p < 0.001). Over half of patients could not tolerate early enteral realimentation and were at higher risk for postoperative complications. Prophylactic drain placement was the only independent modifiable risk factor for delayed oral intake.