Originally Posted by morpheusxeno
Honestly wish the guild welcome addon just allowed direct message on player join.
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Have a look at it, and see if you can identify the part of the code that does the guild welcome message and then look at this page
https://wowpedia.fandom.com/wiki/API_SendChatMessage
to see how you could make it work for whispers.
That said, one thing that occurred to me .. have you considered several people in the guild with the same addon then sends the person a bunch of whispers. Some may feel that is just as spammy as sending it in guild chat. So, you may want to restrict it to say guild masters and officers only for example to limit the automated spam ( that suggested addon may have similar tests to give you an idea of how to validate that way if you chose to). Of course it doesn't stop people manually welcoming then if its an over friendly guild.