Category Archives: Exchange

Exchange 2016 + Skype For Business + New Certificate = Errors?

Changing an expired SSL certificate is easy in Exchange 2016 using the EMC.  A simple click or two, and boom… new certificate!

Unless you have integrated Skype for Business IM into your OWA.

1st Symptom: User Complaints
2nd Symptom: Your exchange logs the following event:

The certificate specified by the InstantMessagingCertificateThumbprint parameter of the Outlook Web App virtual directory wasn’t found in the local certificate store.
Certificate thumbprint:

Yup.. you have a couple of more steps to complete.

STEP#1: Get the new thumbprint

  1. Launch Exchange Management Shell as an Administrator
  2. Execute
  3. Copy the Thumbprint of the certificate that has registered the “W” service
    NOTE: That same certificate may have registered other services like the certificate example below, which has registered IPUWSC services.

STEP#2: Update the OWA virtual directory with the new thumbprint

  1. Launch Exchange Management Shell as an
  2. Execute
    get-owavirtualdirectory | Set-OwaVirtualDirectory -InstantMessagingCertificateThumbprint [THE NEW THUMBPRINT]

STEP#3: Update the OWA configuration file

  1. Open the OWA configuration file located at
    C:\Program Files\Microsoft\Exchange Server\V15\ClientAccess\OWA\web.config
  2. Search the configuration file for “IMCertificateThumbprint”
    Important: If the key does not exist in the web.config, proceed to STEP#3A below
  3. Change the key thumbprint to the new thumbprint value
    <add key=”IMCertificateThumbprint” value=”[THE NEW THUMBPRINT” />
  4. Restart IIS and test IM in OWA
  5. Your Done!  Stop here!

STEP#3A: Update Setting Overrides

  1. Launch Exchange Management Shell as an Administrator
  2. Execute
  1. You should get an output like the following
    Closely note the following values
    – Id   {In the example above, the value is OWA-SKYPE-INTEGRATION
    – Parameters, specifically the IMServerName value {In the example above, the value is
  2. Execute
    Set-SettingOverride -Identity [ID NAME] -Parameters @(“IMServerName=[SERVER NAME]”,”IMCertificateThumbprint=[THE NEW THUMBPRINT]”)
  3. Make sure everything is refreshed by executing the following command
    Get-ExchangeDiagnosticInfo -Server $ENV:COMPUTERNAME -Process Microsoft.Exchange.Directory.TopologyService -Component VariantConfiguration -Argument Refresh
  4. Restart IIS and test IM in OWA

Good Luck!

Exchange UM Voice Auto-Attendant custom greeting and those pesky system prompts

Microsoft Exchange Unified Messaging is a very cool tool to put into your corporate telephony arsenal.  You get a very nice, voice activated auto-attendant with some very nice features.
One feature the Exchange UM team didn’t get fully right is customization of the initial greeting.

Out of the box, your voice enabled AA (auto-attendant) will say:

Thank you for calling [your company name] To reach a specific person, just tell me their name

If you are like ArmgaSys, you will want to customize your greeting via the ECP (Exchange Admin Center).  You hire voice talent and record a really nice greeting along the lines of “Thank you for calling my company, if you know your parties extension, you may dial it now or simply tell me their name”.  You then upload your greeting in the UM and are shocked to hear the following:

Thank you for calling my company, if you know your parties extension, you may dial it now or simply tell me their name. To reach a specific person, just tell me their name.

You just discovered a UM system prompt, specifically the Voice AA prompt which says (in a female voice) “To reach a specific person, just tell me their name”

At this point, you have only one option:  You must replace the system prompt with a audio file containing silence.*  Fortunately, this is very easy to do!

The solution:

  1. On your Exchange UM server, navigate to
    C:\Program Files\Microsoft\Exchange Server\V[#]\UnifiedMessaging\prompts\en\
  2. Delete the file vuiAADsearch_Yes_Custom_No_main.1.wav
  3. Make a copy of Silence-250ms.wav
    (This .wav file is also located in the prompts\en directory)
  4. Rename your copy of the silence file to vuiAADsearch_Yes_Custom_No_main.1.wav

That is it!

Warning! Warning! Warning!
Installing cumulative updates (CU) and service packs will revert this file back to its original state.  You will need to repeat these steps after each CU and Service Pack!


*Some of you will be asking “Why not just delete the file”.  Well, it is a system prompt which means Exchange UM pretty much requires the file to be there.  Deleting the file can (and will) cause your UM service to fail.

Exchange Unified Messaging Doesn’t Start (No Certificate Found)

So, you have updated your SSL certificates in Exchange 2010 to comply with (insert corporate policy here).  All seems well until you receive a frantic call: “Voice Mail is down!”.

A quick search of the event viewer turns up:

The Microsoft Exchange Unified Messaging service was unable to start. More information: “Microsoft.Exchange.UM.UMService.UMServiceException: No certificate was found using the thumbprint ” specified in the UMCertificateThumbprint property of the UMServer object.
   at Microsoft.Exchange. UM.UMService.UMConnectionManagerHelper.TLSConnectionManager.Initialize()
   at Microsoft.Exchange.UM.UMService.UMService.InitializeConnectionManager()
   at Microsoft.Exchange.UM.UMService.UMService.StartService()
   at Microsoft.Exchange.UM.UMService.UMService.OnStartInternal(String[] args)”


You cradle your head in your hands and begin to weep softly.

Fear not!

The Solution

  1. Launch Exchange Management Console from the server hosting the Unified Messaging Role
    Important: Remember to launch with UAC elevated permissions!
  2. Expand and click on Server Configuration
  3. From the server list in the center pane, select the server hosting the Unified Messaging Role
  4. In the lower center pane, you’ll very likely notice the new SSL certificate is not assigned to any services
  5. Right click on the certificate and select Assign Services to Certificate
  6. In the wizard, check the Unified Messaging (UM) service
  7. Finish the wizard and dry your tears!