To investigate pain catastrophizing presentations up to 6 months postoperatively and subsequent changes in pain intensity and physical function. Prospective observational multisite study. Two tertiary care facilities between 2016 and 2019. Adult patients (N=348) undergoing a mastectomy, thoracic surgery, total knee or hip arthroplasty, spinal fusion, or major abdominal surgery. Not applicable. Pain Catastrophizing Scale scores, Defense and Veterans Pain Rating Scale, average pain intensity, and Patient Reported Outcomes Measurement Information System (PROMIS) physical function. Four pain catastrophizing trajectories were identified in 348 surgical patients during the 6 months of postoperative recovery: stable, remitting, worsening, and unremitting. Linear mixed-effects models found that the unremitting trajectory was associated with higher pain intensity over time. The average pain intensity of participants in the remitting trajectory was estimated to decrease at a faster rate over the 6 months after surgery than pain of other trajectories, despite participants reporting high preoperative Pain Catastrophizing Scale and pain scores. Worsening and unremitting trajectories were associated with reduced physical function. Preoperative average pain intensity scores were not associated with postoperative physical function scores, nor were participants' preoperative physical function scores associated with average pain intensity scores postoperatively. Prolonged hospitalization, smoking, and preoperative opioid prescriptions were associated with the unremitting trajectory. Findings suggest that preoperative pain catastrophizing scores alone may not be adequate for estimating long-term patient-reported outcomes during postoperative rehabilitation. Pain catastrophizing has a dynamic presentation and is associated with changes in pain intensity and physical function up to 6 months postoperatively. Routine assessments can inform the delivery of early interventions to surgical patients at risk of experiencing a pain catastrophizing trajectory associated with suboptimal outcomes during rehabilitation. Copyright © 2020 American Congress of Rehabilitation Medicine. All rights reserved.