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Conversation History Not Updating

If your Exchange conversation history is not updating in Outlook, this is most likely because the Skype for Business client cannot detect the Exchange Web Services Location (EWS).

Autodiscover SCP? Not useful to Skype for Business.

The first thing necessary to understand is that, unlike Outlook, Skype for Business is not able to do the Autodiscover by using SCP. The only Autodiscover method that Skype for Business is able to use for this integration is by using DNS.

How does Skype for Business do the Autodiscover?

Skype for Business does the Autodiscover by using the DNS registers for the Autodiscover service. First, it tries to do the Autodiscover by using the address autodiscover.smtpdomain.com, and after that it tries to do it by using SRV, usually _autodiscover._tcp.smtpdomain.com.

Configuring Exchange for Skype for Business

First, you need to configure Autodiscover to Basic, using the following cmdlet:

Get-AutodiscoverVirtualDirectory | Set-AutodiscoverVirtualDirectory  -BasicAuthentication $true

You will also need (if you don’t have it configured) the EWS address (and the DNS entries if needed):

Get-WebServicesVirtualDirectory | Set-WebServicesVirtualDirectory -ExternalUrl https://{EXTERNALEXCHANGEADDRESS}/EWS/exchange.asmx -InternalUrl https://{INTERNALEXCHANGEADDRESS}/EWS/exchange.asmx -BasicAuthentication $true

Certificates

For Skype for Business to work correctly with Exchange, the CAS Servers certificates need to have the Autodiscover address in the SAN. If your SMTP domain is contoso.com, then it needs to have the address autodiscover.contoso.com in the certificate.

Skype for Business is not able to work with other addresses. Don’t try to configure, for instance, the address mail.contoso.com in Autodiscover, since you already have this address in the Exchange Certificate and you ought to keep costs low. In this particular case, Skype for Business will only be able to work with the address autodiscover.contoso.com.

DNS

The DNS configuration can change a lot according to the environment diversity. Below, we show a table with an example where the SIP domain is example.com and the SMTP domain is example.com.

Domain FQDN Type IP/Destination
example.com autodiscover.example.com A CAS Array IP

If the Exchange has the address autodiscover.example.com in its certificate, everything is going to work fine. This configuration needs to be done both in Internal and External Public DNS.

To clarify, Skype for Business tries to find EWS performing these two basic queries:

http://autodiscover.<smtpdomain>/autodiscover/autodiscover.xml
_autodiscover._tcp.<smtpdomain

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