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---- Email getting stuck in spam filter
swa66 - 8:07 am on Feb 28, 2013 (gmt 0)don't send too many messages (the more you send, the more likely it'll be flagged as spam)
Spammers would love to know that same answer :) , so you're not going to find it all that easy.
To not get caught up as a false positive you can make sure to do a few things:
e.g.: rate limit sign-ups for the same account, from the same source IP, ...
make sure the headers of the email are complete (spammers often used to fail to do this properly, some anti-spam still checks on that).
make the content as little "spammy" in nature as you can. Write it neutral and factual, avoid all marketing flair. You've already sold them to get an account anyway.
Send it from a trusted source.
E.g. if you host your website at big name shared hosting: odds are your IP range is already flagged as a source of spam due to your provider selling to offshore professional spammers.
One way around this is to not direct deliver from your MTA, but to configure it to use a smarthost that's allowing you to relay messages - your service provider might offer that as a service - if they don't you can always build your own elsewhere (e.g. behind a business DSL line or so). Even if your provider offers you a smarthost: take care: it might be flagged as a source of spam regardless if they do not actively manage it appropriately.
Aside of that you do have to expect some messages to be flagged as spam. Fact of life.
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