Questions

Redirecting Exchange Mail from SBS 2003 to Hotmail account...

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Redirecting Exchange Mail from SBS 2003 to Hotmail account...

ntraiser
I have been researching most of the morning how to redirect mail from a SBS 2K3 Exchange to an Hotmail account.
I have completed that by creating a contact and through AD > Exchange General > Delivery Options forward to this Hotmail contact.
Stipulations:
1. Mail can NOT reside on Exchange server
--> I did not check the box to leave copy on server - problem solved.
2. The mail needs to appear to be sent by the Exchange account.
Currentlty the recipient is losing the redirected mail to the SPAM filter. Adding the many senders to the safe list isn't an option.
I found within Rules Wiazrd the ability to forward as an attachment but that will then leave a copy on the server. There are legal reason for not allowing the mail to remain on the server.
There?s an option to redirect but that puts me back at square one with mail being left on the server.
Does anyone have a suggestion that can help refocus my research on this issue?
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    Churdoo

    Then your server likely is not complying with current best practices as a sending SMTP server. The company is probably having other outbound email dropped at other recipient servers for the same reason.

    If the server itself can forward email through the site ISP (forward all email through smart-host), then that will be the easiest way, and you won't have to worry about reverse-DNS, etc. because your ISP will take care of all that.

    Otherwise, to have this server send email directly, then the IP that it sends outbound SMTP must be registered in Reverse-DNS as the FQDN of the server, as identified in ESM / your exchange org / Administrative Groups / First Administrative Group / Servers / your server / Protocols / SMTP / default SMTP virtual server / Properties / Delivery / Advanced

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    ntraiser

    thanks for the response, but that think that's taking a step further. my biggest concern at that moment is just getting the mail to forward from hotlist@exchdomain.com with the senders original email as an attachment. this way the client only has to add one email to their whitelist.
    The server side rule, assuming it's server side, to Forward as an attachment is what I need but I can't have a copy of the mail left behind in the exch mailbox.

    I see there's a Permanently Delete It rule but I haven't been able to test if it will apply this rule after forwarding. Will it leave a copy in the Sent folder?

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    Churdoo

    With respect to rules ordering... when you set up these rules in Outlook, you also set their firing order, so that you set the forwarding rule, of course before the delete rule. I do believe these rules will process server side, but you'll have to test that. I would suggest using some other test mailbox, a personal one of yours for example instead of the hotmail as the forwarding recipient to smooth out the process, and then switch to the hotmail mailbox once you have a smooth process.

    If the forward rule leaves a copy in the sent mail folder, then you can create a Mailbox Management Policy on the exchange server and apply the policy to the 1 mailbox, to delete everything out of the mailbox every 1 day -- this will include the Sent Items folder. For that matter, you can forget the delete rule and just let the Mailbox Management Policy delete the inbox too.

    I do have to say however, that by going through the infostore, i.e. into an exchange mailbox and then re-processing with rules, regardless of whatever delete rules you set up, if the client has archiving set up on the infostore (ESM / Exchange Org / Administrative Groups / First Administrative Group / Servers / your server / First Storage Group / Mailbox Store / Properties / General), these emails will be recorded in the archives. period.

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    CG IT

    why are you allowing email into exchange, then forward to hotmail? AND not have the original email reside on Exchange, yet have the original email appear to come from the company email server?

    What your doing is just plain old relaying and not only that, but spoofing or original email to appear to come from the company email server.

    Doesn't sound on the up and up to me.

  • +
    0 Votes
    Churdoo

    Then your server likely is not complying with current best practices as a sending SMTP server. The company is probably having other outbound email dropped at other recipient servers for the same reason.

    If the server itself can forward email through the site ISP (forward all email through smart-host), then that will be the easiest way, and you won't have to worry about reverse-DNS, etc. because your ISP will take care of all that.

    Otherwise, to have this server send email directly, then the IP that it sends outbound SMTP must be registered in Reverse-DNS as the FQDN of the server, as identified in ESM / your exchange org / Administrative Groups / First Administrative Group / Servers / your server / Protocols / SMTP / default SMTP virtual server / Properties / Delivery / Advanced

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    0 Votes
    ntraiser

    thanks for the response, but that think that's taking a step further. my biggest concern at that moment is just getting the mail to forward from hotlist@exchdomain.com with the senders original email as an attachment. this way the client only has to add one email to their whitelist.
    The server side rule, assuming it's server side, to Forward as an attachment is what I need but I can't have a copy of the mail left behind in the exch mailbox.

    I see there's a Permanently Delete It rule but I haven't been able to test if it will apply this rule after forwarding. Will it leave a copy in the Sent folder?

    +
    0 Votes
    Churdoo

    With respect to rules ordering... when you set up these rules in Outlook, you also set their firing order, so that you set the forwarding rule, of course before the delete rule. I do believe these rules will process server side, but you'll have to test that. I would suggest using some other test mailbox, a personal one of yours for example instead of the hotmail as the forwarding recipient to smooth out the process, and then switch to the hotmail mailbox once you have a smooth process.

    If the forward rule leaves a copy in the sent mail folder, then you can create a Mailbox Management Policy on the exchange server and apply the policy to the 1 mailbox, to delete everything out of the mailbox every 1 day -- this will include the Sent Items folder. For that matter, you can forget the delete rule and just let the Mailbox Management Policy delete the inbox too.

    I do have to say however, that by going through the infostore, i.e. into an exchange mailbox and then re-processing with rules, regardless of whatever delete rules you set up, if the client has archiving set up on the infostore (ESM / Exchange Org / Administrative Groups / First Administrative Group / Servers / your server / First Storage Group / Mailbox Store / Properties / General), these emails will be recorded in the archives. period.

    +
    0 Votes
    CG IT

    why are you allowing email into exchange, then forward to hotmail? AND not have the original email reside on Exchange, yet have the original email appear to come from the company email server?

    What your doing is just plain old relaying and not only that, but spoofing or original email to appear to come from the company email server.

    Doesn't sound on the up and up to me.