Exchange 2010 and user multiple SMTP address' defined on their "e-mail address" tab

A quick overview. Have an SBS2011 server running Exchange 2010 that until recently was using POP for main email communications. Just brought everything inhouse and all email operations is now running off Exchange 2010.

While still using POP from a 3rd party, add'l SMTP addresses were created for a certain subset of users, so that their personal web-based ( / gmail, roadrunner, etc) would display in the Global Address List. Everything worked fine when selecting theirwebased accounts as far as addressing an email to that account, and sending/receiving on that account.

However since redirecting all email to the inhouse Exchange, when a user who has a web based SMTP account defined under their Exchange Email Address' tab, (recipient configuration > mailbox > user "email address' tab) tries to either send or forward an email to that web-based account...they don't receive it there. It gets sent but comes right back in on their Exchange account. It never arrives at their g-mail account (as example).

Could use a pointer or two on what to look at. I"ve not been able to even phrase a search argument on this odd-ball to make any progress. Thanks much for any assistance.
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setasoujiroConnect With a Mentor Commented:
I'm not to sure on how you added the external accounts, but normally you would add them as "mail contacts" and not add the mailaddress as an alias on their mailbox on exchange.
Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
Is the Web-based account and internal account having same set to email addresses ? If so this will happen as if the email exists within the environment why would Exchange send it Outside ?

- Rancy
Imtiaz HashamConnect With a Mentor Technical Director / IT ConsultantCommented:
The best way to do this is to create this as an SMTP contact with a different name e.g. adding "-external" to their display name.

Connect answer from setasoujiro & Rancy, however, Rancy is correct because it doesn't go to DNS to check the email address as their email is already found in the same org.
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In case the previous is true , then check out this on how to make mail contacts:
hwtechAuthor Commented:
Guys appreciate the assistance. This is a snap (apologize for the rough editing) - but gives an idea of what the setup is here on the internal user exchnage accounts.

Current Exch Setup
There were mail contacts created for non-company employees, who do volunteer work for example for the company - so that internal employees on Exchange would have these volunteer 3rd party email addresses visible in the exchange address list.

However the internal Exchange email users, who also wanted their 3rd party email address' visible within Exchange, were setup as shown in the attached snapshot. Not sure if this means of establishing their 3rd party email address is my issue? I will say this all worked without problem (the internal exchange employee 3rd party email accounts setup as just described) prior to bringing everything in house.
Manpreet SIngh KhatraConnect With a Mentor Solutions Architect, Project LeadCommented:
Look you should have the External email on a Contact and not Mailbox

- Rancy
Simon Butler (Sembee)Connect With a Mentor ConsultantCommented:
You shouldn't have external email addresses on an internal mailbox. That will confuse Exchange and could stop Exchange delivering email correctly.
If you want external addresses in the GAL, then configure contacts.

hwtechAuthor Commented:
I appreciate the help on this. I don't recall exactly how I came upon setting these external users up as I did, but I did and it appeared to be working correctly until all email operations were moved in-house.

I have deleted the external SMTP address' and created new mail contacts as suggested. That appears to be the ticket as email communications to these external email accounts is now working. Much obliged for the assistance.
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