To compare the ability of different electronic health record alert types to elicit responses from users caring for cancer patients benefiting from goals of care (GOC) conversations. A validated question asking if the user would be surprised by the patient's 6-month mortality was built as an Epic BestPractice Advisory (BPA) alert in three versions-(1) Required on Open chart (pop-up BPA), (2) Required on Close chart (navigator BPA), and (3) Optional Persistent (Storyboard BPA)-randomized using patient medical record number. Meaningful responses were defined as "Yes" or "No," rather than deferral. Data were extracted over 6 months. Alerts appeared for 685 patients during 1,786 outpatient encounters. Measuring encounters where a meaningful response was elicited, rates were highest for Required on Open (94.8% of encounters), compared with Required on Close (90.1%) and Optional Persistent (19.7%) (p < 0.001). Measuring individual alerts to which responses were given, they were most likely meaningful with Optional Persistent (98.3% of responses) and least likely with Required on Open (68.0%) (p < 0.001). Responses of "No," suggesting poor prognosis and prompting GOC, were more likely with Optional Persistent (13.6%) and Required on Open (10.3%) than with Required on Close (7.0%) (p = 0.028). Required alerts had response rates almost five times higher than optional alerts. Timing of alerts affects rates of meaningful responses and possibly the response itself. The alert with the most meaningful responses was also associated with the most interruptions and deferral responses. Considering tradeoffs in these metrics is important in designing clinical decision support to maximize success.