Smartphones offer new opportunities to improve the lives of older adults. Although many older adults are interested in smartphones, most of them face difficulties in self-instruction and need support. Text entry, which is essential for various applications, is one of the most difficult operations to master. Therefore, we propose an assistive typing application that detects input stumbles and provides instructions for typing presented sentences, instead of having human tutors help older adults resolve the input stumbles by themselves. First, we investigated the ways that novice older adults have problems with text entry on smartphones. Next, we confirmed the acceptability of being provided with instructions for text entry by Wizard-of-Oz (WoZ). Then, we constructed an assistive typing application based on the collected data from two user studies. An evaluation with novice older adults (60+) showed that the assistive typing application increased typing speed by 17.2% and reduced input stumble incidence by 59.1% compared with the users' initial performance. Improvement rates were almost the same as those achieved with human tutors.