Office 365 Migration with Cisco IronPort

I ran across an interesting issue recently where a client could not get Autodiscover to work properly during their “rich coexistence” period with an on-prem Exchange 2010 during their migration to Office 365. Autodiscover for an on-prem user would work fine, but as soon as the user had their mailbox moved to Office 365 the Autodiscover process wouldn’t work. The DNS records looked fine and when looking at the log we saw the client would connect to the internal SCP, get a redirect to Office 365 for the correct SMTP address, and then fail. We couldn’t set up a brand new profile for the user internally, but we noticed it would work perfectly ok from an Internet client. Must be something internal at that point, right?

After some more testing we learned a Cisco IronPort was being used for outbound web proxy filtering. As soon as we added an exception for the test machine's IP address we found Autodiscover worked just fine for a cloud user. In the end we added an exception for the FQDNs and Secure web filtering keeping users safe and admins frustrated. Happy migrating.

Adding Speech Languages to an Existing Exchange UM Dial Plan

There have been a few instances lately where I've needed to add a speech language pack to an Exchange Unified Messaging server after a dial plan and auto-attendants have been created. Installing the language pack is no problem, but what you'll find is that the new language is only available to new dial plans and any objects tied to them. You cannot simply install the pack and then select the language for an existing user or auto-attendant.

Here is an example case where I've installed the Portuguese language pack on a server:

But you can see the pack is not available for a dial plan created prior to the installation:

I'm sure the Microsoft answers are either to A - make sure you install the language packs up front, or B - create a new dial plan and auto-attendants, but in my case A was not possible and I had no interest in the effort involved for B.

So, ADSI Edit to the rescue. You can grab the language codes for installed packs from the UM server object properties at CN=<Server Name>, CN=Servers, CN=Exchange Administrative Group (FYDIBOHF23SPDLT), CN=Administrative Groups, CN=<Exchange Org Name>, CN=Microsoft Exchange, CN=Services, CN=Configuration, DC=<Forest>, DC=<TLD>. The msExchUMAvailableLanguages attribute will list the languages installed on the server (1033 is US English):

Now, armed with the language code for Portuguese (1046) you can modify the existing dial plan or auto-attendants objects in the UM AutoAttendant or UM DialPlan containers to support this language. The containers for these objects are found within CN=Exchange Administrative Group (FYDIBOHF23SPDLT), CN=Administrative Groups, CN=<Exchange Org Name>, CN=Microsoft Exchange, CN=Services, CN=Configuration, DC=<Forest>, DC=<TLD>. You can add the language as an option by modifying the msExchUMAvailableLanguages attribute to include the new language code. Here I have added it to an existing plan called Brazil:

You can now see this language appear as an option for the dial plan within the Exchange Management Console:

You can use this same method for an auto-attendant, but I would add the language first to the dial plan the auto-attendant is associated with. Obviously using ADSI Edit incorrectly has potential for causing some serious issues. Proceed at your own risk.

Snow Leopard and Exchange 2007 Integration Notes

Some notes on my experience so far with Apple’s 10.6 Snow Leopard OS and Microsoft Exchange Server 2007:


  • It’s brain-dead. It uses Autodiscover, so e-mail and password is all you need. You get prompted if you’d like it to also configure iCal and your address book.

  • I haven’t tried from home yet, but the external server path is not filled out. Internal picks up EWS/Exchange.asmx URL just fine, but external is blank. I double-checked our Exchange server and this parameter isn’t filled out so that makes sense. The difference here is Outlook assumes the external is the same as internal if this value is blank, but it appears Apple Mail will not. Be sure to set your –ExternalURL parameters on the virtual directories appropriately.


  • Responses to meetings come across as an .ics attachment, no special functionality here. This is especially bad if someone proposes a new time.

  • The Exchange RSS Feeds folder does not integrate with the RSS feeds section in Mail. This would have been nice.

  • Name suggestions are offered from the GAL and your contacts.

  • Rules do not sync.

  • UM voice mails have a built in media control. My codec is set to G.711 and I see embedded QuickTime controls in the message for playback.

  • The actually listing of your notes is displayed in the Marker Felt font. It’s horrendous and tough to read.

  • No out of office assistant.

  • You can add multiple Exchange accounts.


  • You can schedule meetings and invite attendees.

  • You can view free/busy details for attendees.

  • iCal does not differentiate between people and resources as attendees.

  • You can view responses for meetings. Accepted, tentative, declined or unknown.

  • Tasks sync to iCal “To-Dos”. The default view shows all completed items. Hit the iCal preferences to change this view.

  • You can view Delegate calendars and grant access to your calendars and tasks.

  • Name suggestions are offered from the GAL and your contacts.

Address Book

  • My contacts came across just fine.

  • I can’t see the GAL for some reason. The URL in the account settings looks correct, but the GAL is empty. Really strange considering I get GAL-suggestions when typing names in other applications.

I’m sure there are more to come, but despite some of the caveats this is still a huge improvement over Entourage. I’m looking forward to the Outlook for Mac client coming next year, but until then I’ll be using the native applications.