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E-mail goes out with the wrong address

The customer uses SBS 2003 as the server.  His primary e-mail address is joe@apples.com, and that is an Exchange account hosted on his server.  He also has a secondary e-mail address of joe@peaches.com, and that is a POP3 account.

He needs to be able to pick between the two when creating a new message in Outlook, and he can indeed pick from the drop down list on the "Accounts" tab.  But the problem is this: if he picks the peaches.com account, it still goes out as joe@apples.com.  That's what the recipient sees.  And if I go and look at his sent folder, it shows this: Joe Smith (Joe@peaches.com) on behalf of Joe Smith.  So, there is SOME reference to his peaches account, but it's not right.  In other words, his recipients should be seeing an e-mail from joe@peaches.com---just like it used to do before we recently upgraded him to a new computer.  (Both old and new ran XP and Outlook 2003.)

I have tried a few obvious things, such as deleting his joe@peaches.com POP3 account in his Outlook 2003 on his computer and setting it back up.  And, BTW, when I run the "Test Account Settings" in his Outlook, it DOES show up in his Outlook as coming from joe@peaches.com--just like it's supposed to.  But that's the only time I can get it to create an e-mail that says it's from joe@peaches.com.

I also tried to delete the joe@apples.com Exchange account so I could re-do it, but I got an error, saying that I could not "delete the account containing your mail, contact and calendar.  You wil first need to create a new location for your personal data."  So, I gave up on this idea, afraid that I would make things worse.

I also checked the user's setup in SBS 2003, and I deleted the one reference to his peaches.com POP3 account in his "E-Mail Addresses" tab, but that did not help.  I don't know why it was there in the first place, but it was, all during the time he was on his old computer--back when things were working fine.

So, I don't understand why I can't get it where it can send out mail from joe@peaches.com.  I don't understand why those are going out as joe@apples.com.  What can I try?  TIA


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sasllc
Asked:
sasllc
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2 Solutions
 
sasllcAuthor Commented:
One other detail: If I go to create a new e-mail, and choose the joe@peaches.com account from the "Accounts" drop down list, it does say at the top of the message "This message will be sent via pop.peaches.com" (which is the name of the POP3 setup).  But, like I say, the end result going to the recipient is not that at all.
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bobohostCommented:
Something i would try would be creating a new profile.  Don't delete his current one but I have seen many weird issues with Outlook be resolved by creating a new profile.  Sometimes the profile gets corrupt and doesn't work as it should.  When creating the profile though make sure you don't setup the exchange account in cached mode.  This way it won't download all the emails to the computer.
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Alan HardistyCo-OwnerCommented:
Are both apples and peaches account setup on the same SBS server?
Are the accounts separate accounts, or are both addresses setup on one Active Directory account?
If they are setup on the same Active Directory Account then this is your problem.
Ideally, you will want to setup two user accounts, one for apples and one for peaches, then assign send as permissions so that you can send out as both.
I will give you more exact details of what to do once I know how your server / accounts are configured.
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sasllcAuthor Commented:
Alanhardisty, I will try to answer your questions, but I'm not clear on some of the terminology, so I may need some additional guidance on where to look to find acccurate answers.

But I "think" that I'm correct in saying that they are NOT both setup on the SBS server, and I'm assuming that questions 2 and 3 would then not apply???  I'm basing this on my understanding that their apples account is set up in Exchange on this single SBS server, where they host their own e-mail, but the peaches account is a standard POP3 account that is hosted by an outside company.  Everyone in this small office has an @apples.com account for their e-mail, and that all flows through Exchange.  But joe ALSO has a POP3 account, and it is set up as a POP3 account in his Outlook E-Mail Accounts setup.  In other words, in his Outlook, he has two accounts setup--the joe@apples.com as an Exchange account, and the joe@peaches.com as a POP3 account.

Is there some way that something on the SBS server might be set up wrong, causing this to happen?  Where would I look?
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Alan HardistyCo-OwnerCommented:
Okay - if that is the case - leave the server questions alone for now.
On the POP3 accounts, what are you using as your SMTP mail server?
This may highlight the problem if you are using your exchange server as the SMTP mail server instead of your ISP's mail server or any other server.
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sasllcAuthor Commented:
Additional thoughts...it has always been my impression--right or wrong--that the incoming mail on his POP3 account is somehow coming in through their server, possibly through the POP3 connector.  But, in case, I've also assumed that his OUTBOUND messages for his POP3 peaches account go out through the smtp.peaches.com account that is defined in his account setup in Outlook--totally bypassing SBS and Exchange.  Correct?
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Alan HardistyCo-OwnerCommented:
Please check the POP account for POP3 and SMTP server details.
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sasllcAuthor Commented:
OK, hang on...I sent my last comment just as you were sending me comments along the same line...
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sasllcAuthor Commented:
OK....I guess I should start using real e-mail domain names in this discussion in order to get effective assistance.

Joe's Exchange address is actually joe@solutionsforaccounting.com.

Joe's "Server information" in his e-mail account setup is"

Incoming mail server (POP3:) joe.cottontechnologies.com
Outgoing mail server (SMTP:) smtp.cottontechnologies.com

I believe it used to be smtp.registeredsite.com in the past, but I don't know what has taken place in the interim making it now be set to cottontechnologies.com.  But I know that this whole setup DID function just fine back when Joe was on his old computer up until a month ago.

Is there a place in their SBS setup that I should look to see if the server/Exchange is somehow handling the SMTP function?
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sasllcAuthor Commented:
And to clarify...what I should have said is this:

Joe has two accounts setup in Outlook.  

One is an Exchange account, joe@solutionsforaccounting.com

The other account in Outlook is a POP account: joe@cottontechnologies.com.
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Alan HardistyCo-OwnerCommented:
Here is a rather large clue:
The SMTP server for both domains is the same IP address and if the IP Address is your IP address, then the cottontechnologies account is sending out via your own exchange server which would explain the problem.
 

SMTP-Problem.jpg
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sasllcAuthor Commented:
Is this something that I can change in the SBS/Exchange setup to make this not happen?  If so, where do I begin?

Or, is this something that I need to work out with registeredsite.com?

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Alan HardistyCo-OwnerCommented:
Does the IP 209.237.134.xxx point to your SBS server?
If it does, then you could just change the outbound SMTP server of the POP3 account to your ISP's SMTP server and that would resolve the issue - test to make sure.
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Alan HardistyCo-OwnerCommented:
Any updates on this one yet sasllc?
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sasllcAuthor Commented:
No, actually I was in the process of closing it out and awarding points because it will take me a day or two to finalize this, and because your observation is surely the solution to the problem.  I had wondered it that might be the problem, but did not know how to find the same info you found.
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Alan HardistyCo-OwnerCommented:
When you send out mail - what user accounts do you use - the same as the internal user account?
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Alan HardistyCo-OwnerCommented:
I used nslookup from DOS and www.dnsstuff.com for the domain reports.
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sasllcAuthor Commented:
When you say: "When you send out mail - what user accounts do you use - the same as the internal user account?"

Unfortunately, I don't know exactly what you mean, nor where to look to answer correctly.  If you are able to give me some specific guidance, I would like to look into this.  But with this question--just like the whole thing with the IP addresses--I'm somewhat handicapped right now because the person who knows far more about this setup is currently out of the country.  Thus my delay of "a day or two".

But if there is anything else you can help me look at in the meantime, I appreciate it!
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Alan HardistyCo-OwnerCommented:
For POP3 accounts you have to specify a username and a password.  Are these usernames and passwords the same as your exchange username and password?
Please email me via my profile if you would like hands-on assistance.
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sasllcAuthor Commented:
Well, I think they are, but I'm not sure.  I think what I'll do is close this out, then wait to hear from the one who knows more about this than I do, and then if I need hands-on help I will get in touch.  Thanks!
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Alan HardistyCo-OwnerCommented:
Sure - feel free to come back if you need more help.
Thanks
Alan
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sasllcAuthor Commented:
In case anyone ever reviews this discussion, I wanted to present "the end of the story"...I made two changes that completely fixed the problem.  In my Outlook setup for the POP3 account, I changed the SMTP port to 587, and I checked the box that says that outgoing SMTP requires authentication.

Now as to WHY that works, I'll never know....unless someone can explain it to me!
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