Hi all, just taken over looking after the IT at a small company, they have a sbs 2003 server all has worked no problems for years. I have been asked to setup a forward using exchange for one AD user so they can get their email on a web client (gmail). Did the usual of setting up a mail enabled contact with the new email xxx@gmail.com and then went into the delivery options of the AD user and told it to delver to both the ad user and the newly created contact. (I have done this many times and know the process) I tested it and the forward only works if the origianl email came from an addrress in the same domain. i.e. john@domain.com sends sue@domain, sue gets it on here PC in the AD and on her gmail. Any address outside sends sue and email AD accounts gets the email but gmail doesnt. An NDR is created: The following recipient(s) could not be reached: petertest on 07/07/2010 16:40 There was a SMTP communication problem with the recipient's email server. Please contact your system administrator. <ourdomain.com #5.5.0 smtp;550 <gmail address>... Not permitted> The strange thing is that if one of the AD users send an email to the external forward address it goes no problem. I have tried using a couple of different ISP external addresses as forwards to gmail and hotmail none recive the ofrward but all will recieve the email if sent by an outlook or OWA client. THey us BT as a smart host. All external and internal email works except when set as an additioanl delivery location. Like i said above, i have setup contacts and AD users many times andknow this bit is correct. Any advice please :-)

Spoofing protection. The way that Exchange 2003 does forwards on a contact means the message looks like it is coming from the original sender. If the original sending domain is using antispoofing techniques such as SPF, and the receiving server is also using them, then the message will be blocked. Furthermore, as you have said that you are using BT as a smart host, then that is going to be a further problem. BT require knowledge of every domain that passes through their smart host. You cannot list every external domain with BT (they will not let you). Therefore their server is going to reject the message. Sending an email from internal works because the From address is your domain, which BT (and any external host) will accept, because your server is either the correct source or your domain is not using antispoofing techniques. Your only option is to not use forwarding and tell the member of staff to use OWA, rather than Gmail. More secure that way as well. Personally I am always suspicious of forwarding requests, as it usually means the reply comes form the forwarded address rather than the business address and the sender gets used to sending it to a personal address. Simon.Simon Butler, Exchange MVP. http://blog.sembee.co.uk , http://exbpa.com/

Thank you very much for your advice. I did think it may be something along those lines. I wasnt 100% as in my office i have the same setup and it works perfectly the only difference is I do not use BT I use talktalk. Thanks again.

Thank you very much for your advice. I did think it may be something along those lines. I wasnt 100% as in my office i have the same setup and it works perfectly the only difference is I do not use BT I use talktalk. Thanks again. As more sites use the antispoofing techniques, which increases all the time, the ability to do the kind of forwarding that Exchange 2003 carries out will reduce. I am not recommending to any of my clients to depend on it, rather to force the recipient to either use OWA, RPC over HTTPS or be provided with a mobile device. Simon.Simon Butler, Exchange MVP. http://blog.sembee.co.uk , http://exbpa.com/