Exchange 2010 MailTips for Restricted Recipients

We are looking to configure MailTips for users who are sending to a pre-defined list of restricted recipients. We would like to display a mailtip message in the user's outlook (2010, 2013) that lets the user know that the address is a restricted recipient and that the email will not go out.

We have about 100 mailboxes and we have a pre-defined list of about 80 or so restricted SMTP addresses. What is the best\easiest way to configure this in Exchange?
Rammy CharlesSales EngineerAsked:
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Jamie McKillopIT ManagerCommented:
Hello,

How are the users restricted from sending to these SMTP addresses? If they are being restricted by delivery restrictions within Exchange, the "Restricted Recipient" mailtip would apply. You can enable all the mailtips with the following command:

Set-OrganizationConfig -MailTipsAllTipsEnabled

If they are being restricted by some other means, you can setup a custom mailtip. You would need to have a mail object (mailbox, contact, distribution group, etc.) created for each address, if you don't already have them. You can then use the instructions here to create a custom mailtip for each one:

http://technet.microsoft.com/en-us/library/dd638199%28v=exchg.150%29.aspx

-JJ
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Rammy CharlesSales EngineerAuthor Commented:
The SMTP addresses are restricted via our Cisco IronPort. We do not have them in a distribution list as they are external contacts (they are user's personal email addresses, gmail, yahoo).

Would we have to create a custom mailtip for each address?
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Jamie McKillopIT ManagerCommented:
You are going to have to create a contact for each address then set a mailtip on each contact.

-JJ
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Rammy CharlesSales EngineerAuthor Commented:
Thanks.

Also, would it be possible to add these external SMTP addresses to the restricted recipients list in Exchange?
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Rammy CharlesSales EngineerAuthor Commented:
Also, would this possibly work if we were to add the restricted SMTP address in one of the AD\Exchange fields in the user's profile rather than creating a mail contact?
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Jamie McKillopIT ManagerCommented:
What you could do is create a blank member distribution group and add all the SMTP addresses to the email addresses tab on the group. You could then set delivery restrictions on the group.

-JJ
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Rammy CharlesSales EngineerAuthor Commented:
Ok, alternatively can we create a customized mailtip that lets the user know that sending is restricted if they are sending to one of the SMTP addresses in the dist group?
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Jamie McKillopIT ManagerCommented:
Yes, you could do that instead.

-JJ
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Rammy CharlesSales EngineerAuthor Commented:
great, do you perhaps know what the syntax would look like for that in the shell?
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Jamie McKillopIT ManagerCommented:
Set-<RecipientType> <RecipientIdentity> -MailTip "<MailTip text>"
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Rammy CharlesSales EngineerAuthor Commented:
Thanks. What would the recipientType and RecipientIdentity be in this case?
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Jamie McKillopIT ManagerCommented:
RecipientType would be DistributionGroup if that is what you are going to use and ReceipientIdentity would be whatever you call the group.

-JJ
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