A friend of mine had never voted, nor registered to vote. So I made sure she did in 2020 by writing this little script to text her using Twilio to remind her to vote on an increasingly frequent basis as the deadline for registration drew near. She registered pretty quick, actually and it didn't run for that long. Which is lucky, because I ended up discovering a breaking bug on the month roll over.
I ended up having to resort to good old fashioned wheedling and emotional manipulation to get her to actually vote, because she ended up just blocking the number.