TargetAddress, ExternalEmailAddress and Set As External

In co-existence scenarios, the targetAddress attribute is leveraged to accomplish routing to different Exchange organizations by specifying the “final destination” e-mail address. The e-mail domain part of this address can be a non-accepted domain (i.e. other organization). This will enable organizations, when used in conjunction with mail-enabled users or contacts, to provision the (global) address list of their Exchange organization with mail-enabled objects of other organizations, also in a migration co-existence phase. Simply said:

  1. It can allow users in the local organization to select the object from the (global) address list and that object exists in other organizations;
  2. Exchange can route the message to its final destination using the specified targetAddress.

Reason for this blog is that I still see people putting e-mail address in the targetAddress property or the object by scripting against Active Directory (e.g. ADSI), even while they’re scripting using the Exchange Management Shell.

In the Exchange Management Shell, you can set the targetAddress by using the Set-MailContact or Set-MailUser in conjunction with the ExternalEmailAddress parameter, e.g.:

Set-MailContact  michel -ExternalEmailAddress michel@contoso.com

Setting this address is also possible using the Exchange Management Console, which may be more appropriate for testing purposes or a small number of changes (though I’d prefer the less-prone-to-error script any day):

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When utilized in scripts, you can use PowerShell Piping Power (is that abbreviation already taken?) to process (CSV) files or use filtering to select the objects of which you want to configure the targetAddress, e.g.:

Get-MailContact -OrganizationalUnit “contoso.local/Division” -Filter {EmailAddresses -like *@contoso.local} -ResultSize unlimited | Set-MailContact –ExternalEmailAddress “$($_.Alias)@newcompany.local”

Get-Content “users.txt” | Get-MailContact | ForEach{ Set-MailContact $_.Identity -ExternalEmailAddress “$($_.Alias)@newcompany.local”  }

This will configure all mail-enabled contacts in the Division OU with an @contoso.local e-mail address with a target address which consists of the current alias followed by @newcompany.local. The other example uses a text file with names to process contacts and set the targetAddress to the current value of “alias” followed by the external e-mail domain.

Needless to say, the connectors between contoso and newcompany  as well as the accepted domains should be properly configured to route those contoso.local and newcompany.local domains between those organizations. Of course, this also depends on whether you’re using internal or external domain names and if you want those messages to go through the public network or not.

Note that this is also how you can set configure the targetAddress of a local (DirSync’ed) mail-enabled contact with an Office 365 mailbox in a Hybrid setup, for example after moving the mailbox to Office 365. In such case you set the targetAddress to the service domain in a Hybrid Office 365 setup, e.g. mydomain.mail.onmicrosoft.com.

Office 365 and “There are no items to show in this folder”

Be advised that when accessing shared mailboxes on Office 365 using Outlook in online mode, you may experience an issue with Outlook not properly updating the mailbox view.

Instead, Outlook will return a “There are no items to show in this view” message. The folder in the folder navigation pane displayed the proper number of (unread) items in the folder.

This could be the symptom of an issue which was already solved in Exchange 2010 Service Pack 1 Rollup 5. It seems the Office 365 data centers are not running a current version of Exchange, as today I received the message the Office 365 environment is currently being upgraded with Exchange 2010 Service Pack 2. The message also mentions the upgrade is to be completed at the end of the month.

More information on the issue in knowledge base articles kb2500648, announcing the fix is included in Exchange 2010 SP1 RU5.

Until then, the suggested workaround is to click one of the columns twice after which Outlook will update the view properly. Of course, you could also enable cached mode, if your setup and company policy permits (e.g. not running Outlook on terminal server).

Exchange Hybrid deployment and SMTP inspection

When setting up secure SMTP connections, also known as SMTPS or SMTP over TLS (Transport Layer Security), you encounter issues with SMTP obfuscating appliances, like Cisco ASA or PIX.

These appliances contain a feature called fixup protocol smtp, SMTP fixup, (E)SMTP inspect(ion) or Mailguard (Cisco), which – when enabled – limit the number of allowed SMTP verbs or obfuscate parts of SMTP dialogs. This tampering will cause problems when you try to configure SMTPS connections between e-mail servers and will prevent you from configuring a working Exchange Hybrid deployment, where TLS secured communications between the on-premise environment and Office 365 is enforced.

Note: By enforced, I mean it requires TLS which is more strict than opportunistic TLS,  which will attempt to set up TLS before continuing with regular SMTP communications.

You’ll end up with Office 365 specific Receive and Send connectors after setting up your Hybrid configuration using the Hybrid Configuration Wizard (or manually). Then, when sending e-mail between on-premise and Office 365, you notice e-mail doesn’t arrive and will remain queued.

After verifying your ISA or TMG isn’t blocking things (ports are open, SMTP filter not blocking STARTTLS etc), you start troubleshooting the issue by enabling Verbose logging for the Office 365 send connector (of course, this can also be achieved using the Exchange Management Console):

Set-SendConnector “Outbound to Office 365” –ProtocolLoggingLevel Verbose

The logs will by default be generated in the $exinstall \V14\TransportRoles\Logs\ProtocolLog\SmtpSend ($exinstall will contain the Exchange installation path).

If you look at the current log file, you’ll see the following pattern for each possible destination – in the example below the TX2EHSMHS017.bigfish.com – as the local Exchange 2010 hybrid server will try to get the message(s) delivered:

Outbound to Office 365,08CEBBEB07152FBC,0,,65.55.88.22:25,*,,attempting to connect 
Outbound to Office 365,08CEBBEB07152FBC,1,192.168.1.11:51841,65.55.88.22:25,+,, 
Outbound to Office 365,08CEBBEB07152FBC,2,192.168.1.11:51841,65.55.88.22:25,<,220 **********************************************************************************************, 
Outbound to Office 365,08CEBBEB07152FBC,3,192.168.1.11:51841,65.55.88.22:25,>,EHLO mail.contoso.com, 
Outbound to Office 365,08CEBBEB07152FBC,4,192.168.1.11:51841,65.55.88.22:25,<,250-TX2EHSMHS017.bigfish.com Hello [92.70.102.115], 
Outbound to Office 365,08CEBBEB07152FBC,5,192.168.1.11:51841,65.55.88.22:25,<,250-SIZE 157286400, 
Outbound to Office 365,08CEBBEB07152FBC,6,192.168.1.11:51841,65.55.88.22:25,<,250-PIPELINING, 
Outbound to Office 365,08CEBBEB07152FBC,7,192.168.1.11:51841,65.55.88.22:25,<,250-ENHANCEDSTATUSCODES, 
Outbound to Office 365,08CEBBEB07152FBC,8,192.168.1.11:51841,65.55.88.22:25,<,250-XXXXXXXA, 
Outbound to Office 365,08CEBBEB07152FBC,9,192.168.1.11:51841,65.55.88.22:25,<,250-AUTH, 
Outbound to Office 365,08CEBBEB07152FBC,10,192.168.1.11:51841,65.55.88.22:25,<,250-8BITMIME, 
Outbound to Office 365,08CEBBEB07152FBC,11,192.168.1.11:51841,65.55.88.22:25,<,250-BINARYMIME, 
Outbound to Office 365,08CEBBEB07152FBC,12,192.168.1.11:51841,65.55.88.22:25,<,250 XXXXXXXB, 
Outbound to Office 365,08CEBBEB07152FBC,13,192.168.1.11:51841,65.55.88.22:25,*,,Connector is configured to send mail only over TLS connections and remote doesn't support TLS 
Outbound to Office 365,08CEBBEB07152FBC,14,192.168.1.11:51841,65.55.88.22:25,>,QUIT,

As you can notice in this example, the SMTP banner has been turned into stars and AUTH and STARTTLS have been changed by the appliance into XXXXXXXA and XXXXXXXB. This behavior is typical of Cisco’s Mailguard feature; other smtp obfuscating appliances might result in different output. Key indicator is, expected elements are missing or garbled.

In such cases, you need to make sure SMTP traffic between on-premise and Office 365 goes through unfiltered. Depending on the capabilities of the device, you could allow the FOPE addresses to go through unfiltered. If that’s not an option, or you don’t like managing that address set, you need to disable the feature completely.

Note that Cisco is not the only vendor offering SMTP obfuscating products; companies like Checkpoint, Barracuda, Sonicwall or Symantec offer products with the feature mentioned above.

Federation Information could not be received ..

When setting up federation between Exchange organization using the Hybrid Configuration Wizard, to connect your on-premise Exchange environment with Office 365, you may encounter an error message in the 2nd step of the Hybrid Configuration Wizard, Update-HybridConfiguration:

image

When inspecting the Update-HybridConfiguration results, it reads:

Updating hybrid configuration failed with error ‘Subtask Configure execution failed: Creating Organization Relationships.
Execution of the Get-FederationInformation cmdlet had thrown an exception. This may indicate invalid parameters in your Hybrid Configuration settings.
Federation information could not be received from the external organization.
..

The problem lies in the sentence “Federation Information could not be received from external organization”. To see where it goes wrong, you could run Set-HybridConfiguration and Update-HybridConfiguration manually, using additional parameters as shown in the result screen, providing proper credentials and additionally addint the Verbose parameter to increase output logged.

Most of the time this problem comes down to one of the following issues, which can be verified by running the following cmdlet, where example.com is to be replaced by the federated domain:

Get-FederationInformation example.com –Verbose

You’ll probably see the cmdlet going trough the discovery motions using autodiscover, ending up in the same “Federation information could not be received from the external organization” message. When analyzing this output, you’ll see it contains two hints on the potential issues:

Get-FederationInformation : The discovery process returned the following results:
Type=Failure;Url=https://autodiscover.example.com/autodiscover/autodiscover.svc;Exception=Discovery for domain example.com failed.; …

1. Autodiscover
The first issue often overlooked is internal autodiscover not working via DNS or not being set up properly, i.e. split DNS configurations. Some customers don’t configure internal DNS autodiscover records or don’t allow (internal) autodiscover to go through the proxy from inside.

Normally, when using regular clients like Outlook, this isn’t an issue because domain joined clients will be using SCP records from AD. However, federation will use DNS records so you need allow it or set it up in DNS; a CNAME for autodiscover.example.com as well as autodiscover.service.example.com pointing to your hybrid server will suffice.

Also make sure you enable WSSecurity authentication for autodiscover on your hybrid server using:

Set-AutodiscoverVirtualDirectory -Identity ‘autodiscover (Default Web Site)’ –WSSecurityAuthentication $true

2. Proxy rules
In the error message you’ll notice a autodiscover-related request going to /autodiscover/autodiscover.svc. These requests are normally caught by the autodiscover rule (path /autodiscover/*) in ISA or TMG. Issue is, these service requests require unauthenticated traffic. When you turn on logging in TMG, you’ll notice the requests for /autodiscover/autodiscover.svc will be denied.

To solve this issue, and to get federation working, you need to set up an additional ISA/TMG rule pointing to the hybrid server, using the proper public names (don’t forget autodiscover), bound to the OWA listener. You need to allow All Users (as opposed to Authenticated Users), set authentication to “No Authentication, but users can authenticate directly” and configure the following paths:

  • /EWS/Exchange.asmx/wssecurity
  • /Autodiscover/Autodiscover.svc
  • /Autodiscover/Autodiscover.svc/wssecurity

After configuring the rule, you need to put it above all the other Exchange rules, making it the first matching rule when federation traffic hits ISA/TMG.

After applying the rule changes, Get-FederationInfo example.com should work and you can continue with the Hybrid Configuration.

For more information on setting up co-existence, consult the steps provided by the Exchange Deployment Assistent.

Exchange PST Capture Tool released

It took a while, but today the Exchange Team released the long awaited Microsoft Exchange PST Capture Tool (initial version 14.3.16.4). The tool can be used to discover and inject PST files in an Exchange 2010 Exchange Online mailbox or archive.

The tool was originally from Red Gate and known as PST Importer. It’s architecture consists of three components: the central service, (optional) agents for PST discovery, registration and collecting PST files and an administrative console (image by Red Gate):

The online documentation can be found here.

Note that although it’s only supported for Exchange 2010 and Exchange Online, you can use it with Exchange 2007; it’s only untested (and probably unsupported) with that product.

You can read the official announcement here; you can download the tool and the agents here.

Office 365 Generally Available

Today, Office 365 hit general availability in 40 countries, with more to come. The launch was accompanied by a Live Webcast with Steve Ballmer.

Microsoft has is offering Office 365, with accompanying plans, for:

  • Professionals and Small Businesses;
  • Midsize and Enterprise;
  • Education (formerly known as live@edu).

More information on the Office 365 service descriptions, plans and pricing, check here. Note that the information – and pricing – is localized and may vary from country to country. Tony Redmond wrote an interesting article on this, as well as some other interesting facts, here.

Also, and I can’t emphasize this enough, be aware of the limitations of any cloud solution. Not only will the provider set the terms and conditions to which you’ll be subjected, you’ll also need to plan for potential business continuity risks, such as downtime of the service or the patriot act. More on the latter here.