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(+2)

One thing that would allow it but that we don't support yet would be webhooks — when a purchase would get made, an HTTP POST request would be sent to a server of your choice with purchase info, letting you send the e-mail. We don't support that (yet).

A solution you can do right now is to encourage your users to play your game through the itch.io app, and use an app manifest to request an API token — sending this to your server will let you retrieve purchase information for the player, generate discord link for them and let them join the discord server from clicking a button in your game: a pretty low-friction approach if you ask me! (no need for them to open their e-mail at all).

Let me know if you have further thoughts — webhooks have been on my mind for a while but I can't guarantee an ETA for the feature, whereas manifests are working right now.

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Oh, actually Amos, you mention encouraging them to play through the itch app, is there a way to enforce the game only getting played through the app? I can enforce this from my end via the authentication, but it would be so much clearer for the players if there was an itch feature that just said "Only playable through itch client" and didn't allow them to download the build separately.

(+1)

There's no way to do that yet, when we first released the app we promised that it wouldn't replace the website — basically, that the option to download from web would remain there. There's alternative ways to authenticate using the server-side API: https://itch.io/docs/api/serverside — you could ask folks for their e-mail, check that they've indeed purchased the game using that e-mail, and send them an e-mail with their Discord key!