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Gene BlakeFlag for United States of America

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Lync and SSL certificates

So this is a fun one...

Backstory:
We used to house MS Exchange 2010 internally, the company migrated mail services to Office 365 in December/January.

We still use Lync 2010 and house it on an internal server. Lync still references the Exchange servers for Contacts info and for the IM services (Skype for Business). We have not migrated to Skype for Business to handle the telephones yet, but the is coming...

We also have a separate server that has Exchange 2013 that handles the Exchange Unified Messaging and Unified Messaging Call Router Service.

Lync 2010 is running on Server 2008R2.

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What works:

Phones work (can call in to direct lines / can call out from direct office phones)
Voice Mail works (Audio & Audio-to-Email conversion)
Email notification of VMail message; in text of course
IVR (Interactive Voice Response; Response Groups): Takes the call; User can navigate through menus

Problem:
Call gets transferred to a Cust Service rep; whe the rep go to answer the phone, the phone does not connect to the user on hold (the parked call).

Phone says unable to connect. Then the Skype instant messenger says "Call couldn't connect or has ended".

The user is left on hold; in a parked call and the call is eventually dumped into VMail.

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Apparently, on 6-APR we had some SSL Certificates that expired/renewed and the person who was receiving the email for this notification was on vacation at the time

And now we're getting SSL Cert warnings when logging on to the Lync server.

Related??? Probably...

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If it truly is an SSL issue, are there specific certs that need to be installed for Lync  functionality or that Lync needs to reference...

How do I need to handle this?

We used to house external facing sites, but no longer do and I'm sure we don't need to be paying for all the SSL Certs that we are.

What Certs are critical and since I'm pretty sure that the certs have auto-renewed, how do I install these SSL Certs on the servers or where do I need to place them for these servers to reference?

Any help would be greatly appreciated. Thanks.
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Jeff Glover
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Keeping exchange UM on premises and running O365 for mail is not a supported topology, and because of how discovery and service connection points are registered, Lync will also not understand that configuration. In short, you can't do that.
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Thanks to @Ivjeff for the assistance in getting this resolved.

I was nice having someone to bounce ideas off of.