I don't think this implies any lack of familiarity with technology.
1. As MetallicCloud observes, emails sometimes fail to get through because of spam filters. (Though in that case, the resends would be likely to get eaten too.)
2. Emails can get lost in other ways. (Rare but by no means unheard of.)
3. The resending also serves as a way to say "You may have been ignoring my emails; please at least confirm that you've got them" without actually having to say that.
1. As MetallicCloud observes, emails sometimes fail to get through because of spam filters. (Though in that case, the resends would be likely to get eaten too.)
2. Emails can get lost in other ways. (Rare but by no means unheard of.)
3. The resending also serves as a way to say "You may have been ignoring my emails; please at least confirm that you've got them" without actually having to say that.