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pop mail not on exchange server

Posted on 2009-05-05
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Last Modified: 2012-05-06
Experts,
I have a client with sbs2003.  Exchange is setup using pop connector.  I have two additional email accounts that have just recently been setup on the pop/web side of things and have no plans on putting them on the Exchange server as they are mobile and will not be logging into the network to check their email.

My problem is that when someone in the office using exchange tries to email something to that person that isn't setup on the exchange server (entering full email address) the exchange server tries to find that address internally and she gets a NDR of not being able to find the mail receipient.  Is there a way to get around this?  Please let me know if more info is need and I will gladly give it.
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Question by:andlemir
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by:Raymond Jansen
ID: 24307457
In the properties of the smtp connector, there is an option to deliver mail with unresolved recepeints to a diiferent server. Maybe you can use this.

Ray
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by:zelron22
ID: 24307503
The POP users each need a mail enabled contact set up through AD users and computers.  When asked to enter an address, enter their pop account address.

After about 5 minutes (assuming your Recipient Update Service is working correctly) the contacts should be stamped with an internal address that your users can use to send email to the POP users.  
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by:Rob Williams
ID: 24309249
Why not have the pop accounts downloaded by Exchange and set the remote users up to use rpc/http. Other than having to enter a password when they first open Outlook, they will see no difference, you would have consistency for all users, the mail is downloaded to the user more securely using SSL, and there would be a backup copy on the Exchange server.

If not familiar with rpc/http:
http://www.lan-2-wan.com/SBS.htm#q5
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Author Comment

by:andlemir
ID: 24310597
Thanks for the quick replies everyone!  I will try to address everyone's suggestions.

r-jansen
Not seeing where that option is under the SMTP connector, unless the wording is completely different.

zelron22
I don't see where I can specify the address in this manor, for when I create a user account for them and choose to setup an exchange mailbox, I have to use the local/stores info.  I can't enter this information.  Are you speaking about a different place?  Am I missing your point?

Rob
Thanks for the suggestion, but they are not wanting to go in this direction.  They won't be checking with their laptops anyway.  Most likely via smart phones.
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Author Comment

by:andlemir
ID: 24310635
Perhaps I can ask the question another way?

How can you tell exchange that you want email to be automatically forwarded out to the pop/internet side of things, even if the email is going to someone in the @companyname.com address?

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by:Rob Williams
ID: 24310648
Not sure that you can.

Many smartphones are supplied with their own e-mail address. If so one common solution is create an account for the user, download the mail, and have it forward a copy to a contact. The contact is set up with the users name (must be slightly different) and the smartphone mail account so it is sent directly to it.

No chance you are using Windows mobile devices? If so they will sync directly with Exchange very nicely.
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Author Comment

by:andlemir
ID: 24310672
So its safe to say that when you setup exchange, if you are part of the exchange server and you send an email to someone else in the company you can never tell exchange to send it externally and not internally?
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by:Rob Williams
ID: 24310718
To the best of my knowledge you are correct, especially with SBS which has a few minor Exchange limitations.

However, having said that, where you are not receiving e-mail via SMTP and the external DNS MX records do not resolve to your IP, I wonder if it would be possible for all mail to be sent externally to the POP service provider, and never forwarded locally. Customizing Exchange is not a strong point for me, but I assume if that would work; the recipient policies would have to be changed, internal DNS records changed, existing mail accounts in the various profiles edited, and a few other changes. i.e. probably not a simple task.

Perhaps there are ways I am not familiar with to only do so with some accounts.
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by:zelron22
ID: 24310937
My suggestion was to set up a mail enabled contact, not a user with a mailbox.

In AD users and computers, right click on a container and choose New Contact.  
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Author Comment

by:andlemir
ID: 24315189
zelron:

Thought of that too, but when I do this is gives me an error saying

"A configuration error in the e-mail system caused the message to bounce between two servers or to be forwarded between two recipients.  Contact your administrator.

            <company.net #5.4.6>"

Am I maybe not setting something up correctly here?  Perhaps I should just setup his phone to sync directly with exchange?  I thought this wasn't possible though with Blackberry?
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Author Comment

by:andlemir
ID: 24316000
one would think that if you have the smtp connector set to send all mail through mail.company.net that exchange would automatically send email out that way regardless, but more importantly if it couldn't find that email address internally to begin with.........I guess this isn't the case though?
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by:zelron22
ID: 24316017
Okay, I'm confused.  Let's say a normal user on your customer's exchange server has an email address of user@internaldomain.com.  Do the POP users have a different domain, such as user@popdomain.com?  If that's the case, have you also set the Exchange server up to handle @popdomain.com mail?  If so, that's why you're getting those errors and NDRs are being generated.

If users want to POP their mail, then you set up a mailbox for them, and you enable POP so they can connect to the server and dump their mail.  This would be a mailbox with an address of user@internaldomain.com.  

Any phone that supports Active Sync can be synched up using Active Sync, assuming that you have secured your server with a certificate.  It requires some configuration, but is possible.

If I'm not right about these assumptions, please clarify the setup, use dummy domains or something, and what you want the end result to be.  If these users all work for the same company, they should all have the same email domain (unless management or marketing has some branding issue and you need multiple domains).  You should not need to set up POP on the Exchange server unless all else fails first.
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by:zelron22
ID: 24316234
No, it's not the case.  Even if you have a smarthost set up, that is only for mail to a domain that the Exchange server isn't set up to handle.
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Author Comment

by:andlemir
ID: 24316425
Sorry for the confusion

all users on the domain are setup through the pop connector.

Internal addresses are @company.local
External addresses are @company.net
smtp connector set to forward mail through smart host mail.company.net (see pic)

The users that I'm trying to setup (2 of them) are new and will have nothing to do with the domain.  They will not be logging into it or using anything off of it.  Therefore I didn't want to create an exchange mailbox for them and have it just fill up because they never checked it.  Also, there is no way to set exchange to leave a copy of the message on the server, so if the exchange server pops the account when a new email comes in before the phone, then the user will never get the message on their phone.

Their phones are setup to hit their pop email address (@company.net).  They can email to the office and the domain fine, but when someone in the office on the domain tries to respond they are issued an error that the person doesn't exist.

I originally thought, no big deal, I'll just create a mail enabled contact for that person and set the email address of @company.net and exchange will know to externally push that email out.  When I do that I get the "A configuration error in the e-mail system caused the message to bounce between two servers or to be forwarded between two recipients.  Contact your administrator. <company.net #5.4.6>"

Does this help to understand the situation?
Picture-2.png
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by:Rob Williams
ID: 24316584
Again, I do not believe this is possible where Exchange is set up to internally to 'listen' for mail destined for the "company" domain.
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Author Comment

by:andlemir
ID: 24316668
I understand that Rob, but that is not what I am wanting to happen (unless I'm just misreading what you are saying).  All I want is a exchange to send an email out from company.local to company.net (which is the pop side of things) instead of only staying internal and saying that it can't find a person to send it to.
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by:Rob Williams
ID: 24316746
I understand that, and I may be wrong, but if Exchange believes it is managing the MyCompany domain internal and/or external, it will intercept all mail destined for that domain name, and not forward it outside of the server itself. I cannot help with doing so, but it may be possible to reconfigure it to forward ALL mail, but I do not think it is possible for it to do so for only non existent accounts. Assuming it is possible to have it forward all mail, it is not as simple as "throwing a switch".
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zelron22 earned 250 total points
ID: 24317210
RobWill is correct.  No offense, but this is so wrong and that's why it's so confusing.

First, do the users in the office get mail from the internet delivered to an @company.net address?  I suspect the answer to this is Yes.
Second, you say that the external users' phones are set to pop their @company.net mail.  How? What are they pointing to?  Because, if they're pointing to the exchange server and there is no mailbox there, there's nothing for them to POP.

An Exchange POP connector is used to allow users to connect to the Exchange server and pull email FROM the Exchange server.  If you want Exchange to poll a POP mailbox, I believe you need to install a third party application.

Are the external users employees of the company?  This is how it should be set up if they are.

@internetemaildomain.xxx (.net, .com, whatever) is your publicly available domain for all of your employees to access.  This can be used internally or externally.
The phones are then set to POP their mail FROM the mailboxes on the Exchange server.  The email address they have will be the same domain, i.e. @internetemaildomain.xxx.

If they aren't employees, then they should have their own email addresses at their own domains, e.g. user@yahoo.com, or user@gmail.com, or user@othercompany.com.

Then you set up mail enabled contacts for these users and assign the appropriate user@yahoo/gmail/othercompany.com.  5 minutes after you create the mail enabled contact, they'll be assigned an email address from your @internetemaildomain.xxx domain.  Internal users can then send to the users using user@internetemaildomain.xxx which then gets forwarded on to the user@yahoo/gmail/othercompany.com.

What you've done (no offense) is overcomplicated it.  It's this simple, either they're employees in which case everyone uses the same domain or their not employees in which case you can set up the contact and forward the mail that way, while allowing them to use one of your company addresses to receive mail.

Now, if you want them to actually be able to use a mailbox, send/receive, etc. because they are employees, you can set up Active Sync instead of having them POP their email.  As I said, POP is really the choice of last resort.

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by:Rob Williams
ID: 24317292
Hi zelron22. Just to clarify one point. SBS (with Exchange) has a feature they call the POP connector which retrieves mail from an off site service in a similar way that a mail client would and drops it in the user's appropriate mailbox. This is meant to be a temporary migration feature to move users from an existing client to ISP pop account configuration, to full Exchange with SMTP, but some folk continue to use it. The complication as I see it is the mail is hosted offsite with the same domain name as is used internally, as a result it will never forward mail outside of the local network. It of course is also not the way Exchnage was intended to be used.

SBS by default does not enable POP access to Exchnage by clients, but does by default configure accessing POP mail accounts, by Exchnge, from an existing hosted service. as mentione this is intended to be temporary.
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Author Comment

by:andlemir
ID: 24317437
zelron, you won't offend me.....don't worry about that.  I'm the first to say I don't know everything, and this is one of those area's that I fall short in, that is why I like to ask the experts and better learn to do things right, logically and as simple as possible.

Having said that, Robwill, you hit the nail on the head!  That is where I have a misunderstanding from what I had learned in the past.  I did not know that this was meant to be a temporary setting.  There are two main reason why I tend to go this route with small businesses, 1)because of the headaches that I've had with mxrecords and local ISP's (usually non-T1 connections, i.e. AT&T, Comcast) and 2)because of the GREAT spam filtering capabilities that the actual email host does so that a lot of junk never even makes it to the exchange server.

Should this be done differently then?  What would you suggest?  I definitely want to learn a much better way to deal with this in the future if I come across it again.

I appreciate your patience on this, and I'm sorry this has turned into such an ordeal.  I really didn't think it was going to be a huge issue.
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Assisted Solution

by:Rob Williams
Rob Williams earned 250 total points
ID: 24317588
It is not a problem to continue with the SBS connector, but it does present some issues, and it cannot be set to retrieve mail to any less than every 15 minutes. Some users get quite frustrated when an e-mail and a reply can take 1/2 hour.

Ideally you want to set up DNS records and MX records created for your domain to point the external IP of the SBS. Other than that everything should already be in place. You can even leave the pop connector running until you are happy everything is transfered over, and MX records are changed. SBS can use both simultaneously.

I agree the spam filtering feature by your ISP is great. Exchange with all the updates will filter quite a bit of spam but definitely not as much. You may want to consider a 3rd party service like www.exchangedefender.com that will re-route your mail through their servers to you. This gives you the direct SMTP features of Exchange, plus mail filtering, and web access if your server is down, to mail you have not yet received.

If connecting remotely using PC's or smart phones you should also consider an SSL certificate for your server. They are available for $40+ from GoDaddy or RapidSSL. This makes it much easier to set up smart phones with active sync, or when using a browser.
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Expert Comment

by:zelron22
ID: 24317853
Woof!  Glad that's been hammered out!  

I've used (and still use Postini (www.postini.com) which is now owned by Google.  And they've started to offer mail archiving and a few other services which we don't currently use.

Good luck.  
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Author Closing Comment

by:andlemir
ID: 31578133
Thank you so much for taking the time to deal with me and this situation.  You two have been a HUGE help!  I will be making the changes to properly set things up from here on out.  Thanks for the great info and response times!
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Expert Comment

by:Rob Williams
ID: 24337281
Thanks andlemir. Good luck with the changes.
If you do switch to using SMTP/Exchange, with 2003 the spam filtering is not automatically enabled. You need to have all service packs installed, and then do a search for "Intelligent Message Filtering", or see the following article. It's quite easy to enable, and I find deals with 80% of spam, but that varys depending on the source.
http://www.msexchange.org/tutorials/microsoft-exchange-intelligent-message-filter.html
Cheers!
--Rob
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Author Comment

by:andlemir
ID: 24339316
Thanks for the additional info Rob.  Looks like we are going to still be able to properly set the exchange server up, and still be able to route things through the outside mail hosts scanners, so I'm not going to have to worry about needing additional services.  Thanks again!
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