cgmendla, you've come to the right place for help. Making sure that all the messages get to your son is important. We appreciate all the troubleshooting that you've done on your own & the information that you've provided us. We do not have an updated Windows desktop version of Messages+. Let's figure this out. Are both of your phones fully updated with the newest software? Is your Windows computer updated with necessary software updates? Do you by chance have another PC to send these texts from to make sure it is not isolated to one device? AliciaD_VZW