Microsoft Remote Connectivity Analyzer

Screenshot 2015-11-07 22.04.57

Sometimes being an Apple admin in an org with a largely Microsoft infrastructure can be a bit of a chore.

It’s not uncommon to hear of Windows admins dismissing issues as being an “Apple” issue without actually expending any effort to look into the issues at all.

However, I’ve been fortunate in that I’ve been able to bend the ear of several sympathetic Windows admins & this has lead to posts such as “How To: Check Your Active Directory Domains Time” & “OSX & AD Certificate Requests, some tips”.

This post is another of those ilk & one that came up quite recently in the Slack & I mentioned this in my JNUC 2015 talks Q&A too, thought it would be a good time to share.

Microsoft Remote Connectivity Analyzer

If you have Lync, Exchange on premise, an O365 hosted Exchange or a hybrid deployment, then at times you might have needed to troubleshoot client OS X & iOS client connectivity or may have to in the future.

Well since 2009 Microsoft have had an online tool that may help, Microsoft Remote Connectivity Analyzer.

NOTE: Lync/Skype For Business can be largely interchanged within this post. I'm sure the tool will be updated to reflect Lync's new name soon.

As the name suggests, this tool analyses remote connectivity for some Microsoft services.

Before we proceed, Microsoft do more than once advise the following:

“To use this tool, you must enter the credentials of a working account from the Exchange domain you want to test. To avoid the risk of your working credentials being exploited and compromising the security of your Exchange environment, we strongly recommend that you create a test account for the purpose of using this tool, and delete this account immediately after you’ve completed the connectivity testing.”


Before we proceed, let’s quickly talk about Autodiscover for both Exchange & Lync clients

Properly setup Autodiscover can greatly simplify adding accounts to Exchange & Lync clients, all you should need to do is supply the users credentials should then “Autodiscover” the server settings.

These are polled periodically (client depending, Outlook for Mac & PC do poll for example. Not iOS’s So that if Autodiscover is properly configured & a mailbox is moved to another server, then Autodiscover should tell the client & the client then updates it’s settings with the new server details.

This can greatly lower administrative overhead & is well worth implementing.

Below are I’ve highlighted some of the options in their respective tabs that are pertinent to those of us whom administer & support Apple products.

Exchange Server

All tests under this tab are for on premise Exchange or can be used for hybrid Exchange installs.

Screenshot 2015-11-07 22.04.57

Microsoft Exchange ActiveSync Connectivity Tests

These are largely relevant for mobile clients, for example iOS’s & Outlook for Android & iOS both leverage ActiveSync to connect to Exchange.

However, it’s rare, but some clients for OS X might use this protocol.

Microsoft Exchange Web Services Connectivity Tests

Both Outlook 2011 & Outlook 2016 for Mac connect to Exchange via Exchange Web Services (often abbreviated to EWS).

Microsoft Office Outlook Connectivity Tests

The 1st test offered under this heading (Outlook Connectivity) only tests MAPI & RPC over HTTP connectivity, which are used by the Windows Outlook clients, so ignore.

The 2nd test “Outlook Autodiscover”, can be used to test Autodiscover for both Mac & Windows Outlook clients, as well as iOS & Outlook for Android & iOS.

Lync/OCS Server

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Microsoft Lync Tests

These two tests should be pretty self explanatory given the above information in the Exchange section.

They work across for all Microsoft Lync & Skype for Business clients, including on & off premise. If a third party app is used, I’m sure they could help track down connectivity issues with them too.

Microsoft Office Communications Server Tests

Communicator was the old name/version of Lync, which as stated is now being renamed/replaced with Skype for Business.

I hope not many orgs are still running Communicator Server.

Office 365

If your on Office 365 then there is a, at time of writing, beta tab to test Office 365 connectivity.

Screenshot 2015-11-07 23.30.07

Office 365 General Tests

The 1st two tests, “Office 365 Exchange Domain Name Server (DNS) Connectivity Test” & “Office 365 Lync Domain Name Server (DNS) Connectivity Test” will test that the custom DNS settings for your Office 365 instance are correct.

The last test, “Office 365 Single Sign-On Test”, will try & validate you credentials against Office 365 as well as some basic Active Directory Federated Services (ADFS) testing against O365.

Microsoft Exchange ActiveSync Connectivity Tests, Microsoft Exchange Web Services Connectivity Tests & Microsoft Office Outlook Connectivity Tests

These are all as mentioned above, however these will target O365 Exchange environments.

If you have a hybrid Exchange, it may be worth checking both here & on-prem.

Free/Busy Test

This test will help make sure that Free/Busy information is being populated on O365 & if using a hybrid Exchange, to your on-prem instance & vice versa.

That’s all the Mule wrote…

So, that’s it, I hope the above has been decent enough overview for you to find it of use.

If you sadly have some Windows colleagues as mentioned at the start of this post, I hope this may help prove some misconfigurations that are amended & then save you some time in client management & troubleshooting.

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