Replying to Emails in Outlook

[quiksil903]

So this has been frustrating the dickens out of me:

Say I have a domain (www.mydomain.com) and I want to create a catch-all type mail account for it. I dont' want to actually give out this account so I create other mail accounts redirecting to it.

So I have master@mydomain.com and biff@mydomain.com where biff is the redirect and master is...well...the master

I'm using outlook 2002 as my mail client. all mail messages are currently being forwarded to master@mydomain.com

My problem and my question is how do I reply to a message sent to biff@mydomain.com (and therefore automatically forwarded to master@mydomain.com) without actually showing the master address as the sender?

I'm looking to create some sort of rule or option that allows all replies to appear to be coming from the e-mail address it was originally sent to (redirects included)

Any thoughts? I know that this is possible but MS help is a bunch of dogfood and won't tell me anything. I figured I would come to the only place to get questions answered...

 

[JustinLerner]

I believe to create a 'catch-all' e-mails, you really need an e-mail server program with the ability to create a 'null' type e-mail alias which accepts any alias. As far as I know, when you send any e-mail from an Outlook client and attempt to send as any other name (spoof) which is not defined in Outlook for the profile in use, the Outlook client sends the e-mail 'on behalf of the spoofed alias' from your account. This is to prevent deception in e-mailing by someone with one address pretending to be an address by another name. This was also probably done by MS to thwart SPAM/UCE/UBE and illegal hijacking or proxying, forwarding, or passthrough with an apparent sender name which is not the real sender. (Some ISP's, like Earthlink, Prodigy, MSN, etc, also block all SMTP passthrough to external (non-ISP) e-mail servers as part of this effor to eliminate SPAM).

If e-mails are forwarded from a catch all to your specific e-mail address using a rule when e-mails are received having any aliases which you specify to your actual e-mail address.
For example, you want to receive all e-mail for postmaster@mydomain.com, webmaster@mydomain.com, administration@mydomain.com all at one real e-mail address call yourname@mydomain.com. You would set up a catch all that filters and forwards any of these specific aliases (or misspelling variations) to your own e-mail address.

I don't know if the Outlook 2000/XP client can spoof an alias address which is not a real e-mail profile e-mail account name in Outlook. MS should not provide you with any technical info about bypassing their security features. If you have your own server (not remote), and you don't need to retrieve your e-mail to your Outlook client through your ISP or assuming your ISP doesnt' block SMTP traffic attempting to passthrough it's access connectors, then you can use any other e-mail program like Eudora to spoof e-mail names from your e-mail sending client.

Once again, if your setup is like below and your ISP blocks SMTP traffic attempting to passthrough the ISP, then you are out of luck.
Outlook Client PC ----- ISP ----- yourdomainserver.com [on the Internet somewhere]

If your ISP blocks SMTP passthrough traffic, then it may be possible to do either of the following, which are more difficult.
1. Setup an on demand tunnel (any IP tunnel type that is supported, like PPTP) from yourdomainserver.com to your Client PC and use this to transfer all e-mail to your client. (You still need an e-mail client capable of spoofing e-mail names.)
2. It may be possible to setup secure socket connections (SSL) to your e-mail server on yourdomainserver.com and setup and use the SSL connections from your appropriate e-mail client capable of e-mail address spoofing.

 

[IcemanJer]

You can either set the REPLY-TO value to biff@mydomain.com, or have your email entryy as biff@mydomain.com, but for the login and password for grabbing stuff off of your mail server use master@mydomain.com's username and password.

 

[JustinLerner]

Versions of Outlook since at least Outlook 97 will enforce a SEND ON BEHALF insertion in the FROM field of an e-mail when any other FROM alias than that which is in REPLY TO value of the OUTLOOK PROFILE is used.

So what IcemanJer says will work with only the ONE ALIAS you specify as the REPLY TO e-mail address in your OUTLOOK PROFILE unless you setup multiple PROFILES for EACH e-mail alias.
Anyhow, like I already said, if your e-mail server is remote (not local) and your ISP does not allow SMTP traffic passthrough, then the above will not work without some other tunneling or SSL setup.

Still, a real catch all e-mail setup can only be setup on a e-mail server, which can then forward all e-mail to any account or filter and forward. For an e-mail client to receive e-mail from a POP or IMAP server, it needs configuration for each account name (e-mail alias) that will be 'caught' or received. This is obviously not a 'catch all' setup, but individually configured for each address to receive.

To reply to multiple aliases with a single e-mail PROFILE and actual single e-mail address will require setup of multiple Internet E-mail Services to your appropriate or main OUTLOOK PROFILE. If your ISP doesn't block SMTP passthrough traffic (traffic sent by you to your e-mail server while connected to their POP), then you can use multiple profiles and multiple aliases as mentioned above and in the reply by IcemanJer, other wise all additional replies by any other e-mail alias will have a "SEND ON BEHALF OF" in the FROM field. Filtering (rules) for your receiving OUTLOOK client profile is still recommended. Additionally, if you use multiple e-mail addresses, multiple Personal Folders for corresponding e-mails might be sensible. This obviously makes things more and more complex.

 

[quiksil903]

so you're saying that i can set up outlook accounts for aliases even if they aren't actual mailboxes (just redirects)?

i think i need to enable at least one of the aliases as a mailbox if i want to have an outgoing mail address that isn't my "master" (because outlook appends that stupid little "this e-mail was actually sent from this configured smtp setup" and that had my master on it already).

for example. i sent an e-mail from biff@mydomain.com, but it said literally 'biff guy' (master@mydomain.com) because that was the only configured smtp setup. i set up one of the aliases as an account so there is a different smtp suffix and my master won't show up.

things "seem" to be working now. but why woudl i want to create additional mail accounts for additional aliases. as long as i'm not giving out my master address in the reply (i assure this by specifiying a reply to address and having the additional alias@domain.com smtp setup for the suffix), then i shouldn't have to configure another account....right?

would any of my problems be solved iwth IMAP? i think my server supports it.

my isp is not bouncing anything since i've had it authenticate the outgoing server. right now it's a lan setup at the office and i'm using my server's smtp info...

any more thoughts? because right now my set up seems overly complicated:

one master@mydomain.com account with both incoming and outgoing setup
one biff@mydomain.com account with both incoming and outgoing setup
one alias@mydomain.com which uses the incoming and outgoing from the others

and a bunch of rules for sorting...

so...lengthy reply to a lengthy reply. any more thoughts? (thanks so much for the help thus far)