Are you receiving a rejection or failed email response? If it is being rejected you should get an email explaining why which will be sent (although you will need to specify a correct from / reply-to email address to receive this).
The first thing I would check is if the IP you are sending from has been blacklisted by any spam services - most deliverability issues I have experienced have been due to this. You can check a fairly extensive list of spam blacklists (together with some additional email validation services) at MX Toolbox
If everything appears fine there it may be due to Gmail's fairly strict antispam criteria. To be accepted, an email should contain in the headers a valid email address for Return-Path
. If this is not valid then there must be a Reply-To
header with a valid email address.
Another important weapon in Googles antispam arsenal is SPF record checking - essentially a way of validating that an IP address is authorised to send email for a particular domain. This is worth checking however as far as I am aware a missing SPF record will only cause the mail to go into spam rather than not be delivered.