Student online learning readiness (SOLR) has been identified as being closely associated with the success of learning in online environments. Online learning orientations have also been used as a key intervention to support students. However, the evaluation practice and research of online learning orientation design are limited. This research studied the effects of an orientation course on SOLR, using a multiyear design-based research with a one-group pretest and posttest method as the evaluation measurement. The design and implementation of a self-paced orientation course in Canvas learning management system was detailed as the intervention. A 20-item SOLR questionnaire was selected as the pretest and posttest instrument. After the initial cycles, a sample of 2,590 college students were invited to participate in the 2017 orientation and respond to the pretest and posttest. Because separate consent forms were distributed and collected at the pretest and posttest stages, the researcher was able to use 445 pretest and 624 posttest datasets. The independent samples t-test results indicated statistically significant improvement of SOLR competencies. The exploratory factor analysis results also indicated changes of items associated with the SOLR constructs. The reliability coefficients of all subscales were > 0.90, with an increase in the reliability of the SOLR instrument as a whole from pretest ([alpha] = 0.92) to posttest ([alpha] = 0.95). Implications for the design and evaluation of online learning orientations and preparing student online learning readiness are discussed toward future design and implementation.