@jonmasters once the reseed button is pressed, everyone who has downloaded the torrent at any point will be messaged, even if they are already seeding that torrent. the problem could be simply that neither you or the person trying to download are able to connect to one another. this is a very common occurrence in torrenting, sadly.
the vast majority of users depend that their client can initiate a connection, because they're unable to receive incoming connections. for this to occur, the other party needs to be reachable. when all peers are behind this limitation, that is, when all peers can only initiate a request but not receive, they are unreachable.
torrents with very few seeders are susceptible to being in this limbo where the person who has the files can never reach the person trying to download.
making torrents freeleech usually helps overcome this because, with lots of people trying to download, the more likely it is that the seeder will be able to reach someone. and in this case, this someone becomes a "hub" that is simultaneously downloading and uploading to the other users who cannot connect to the original seeder.
i'll stop here cause its too long already, but if you're curious about what causes peers to be unreachable or solutions to circumvent this, feel free to ask.