During May and June (the Meiyu season) of 2017, Taiwan was affected by three heavy frontal rainfall events, which led to large economic losses. Using satellite observations and reanalysis data, this study investigates the impact of boreal summer intra-seasonal oscillations (BSISOs, including a 30–60 day ISO mode named BSISO1 and a 10–30 day ISO mode named BSISO2) on the heavy rainfall events in Taiwan during the 2017 Meiyu season. Our examinations show that BSISO2 is more important than BSISO1 in determining the formation of heavy rainfall events in Taiwan during the 2017 Meiyu season. The heavy rainfall events generally formed in Taiwan at phases 4–6 of BSISO2, when the enhanced southwesterly wind and moisture flux convergence center propagate northward into the Taiwan area. In addition, we examined the forecast rainfall data (at lead times of one day to 16 days) obtained from the National Centers for Environmental Prediction Global Forecast System (NCEPgfs) and the Taiwan Central Weather Bureau Global Forecast System (CWBgfs). Our results show that the better the model’s capability in forecasting the BSISO2 index is, the better the model’s capability in forecasting the timing of rainfall formation in Taiwan during the 2017 Meiyu season is. These findings highlight the importance of BSISO2 in affecting the rainfall characteristics in East Asia during the Meiyu season.