[natrius]

Does any service actually let you send emails through a user's account via some sort of API? If you're just using their username and password to log into the service and send the email as them, that strikes me as considerably sketchy. Don't do it. Send the invite from your domain.

I don't know how to avoid spam filters other than what Googling for it gives me. It'd be interesting to hear what has worked from people who have actually had to do it.

[ojbyrne]

The API you're talking about is authenticated SMTP. I think he's just talking about setting the From: header.

I've seen both approaches - but it seems clear you'll get a better response using the individual's email.

[natrius]

Does anything other than GMail provide SMTP?

If he's just talking about setting the From: header, wouldn't that make it even more likely to be marked as spam?

[evgen]

No mail provider is going to be stupid enough to let a client application relay mail without the user inputing a username/password combo, and I would hope that most users these days are not dumb enough to blindly hand their mail authentication credentials to some random website. This leaves two options, forging the From: header or sending from your own domain. The former will get marked as spam by anything honoring/using SPF, so that is not really a smart move. The best option is to send it from your own site but include the inviters name at the start of the subject line (e.g. Subject: [e-mail] invites you to try foo.com)

[ojbyrne]

I used two pretty big sites (kayak.com and nytimes.com) in the last couple of days that put my email in the From: header. Admittedly as a result of my specific action, but that's a user contract issue rather than getting through spam filters - which they didn't seem to have a problem with.

[natrius]

"I would hope that most users these days are not dumb enough to blindly hand their mail authentication credentials to some random website."

That's exactly what most sites that let you import contacts ask their users to do.