I've been having this issue for quite some time as well, and have been working with a Microsoft Skype for Business (SfB) support engineer on it. To be certain it's the same, or similar-enough issue, here's the setup I've been working with (or against it seems):
Signing into Skype and instant messaging are affected. Here the problem ‘Signing into Skype’ corresponds to the problem under discussion. If you navigate to the end of the page, you will see a heading “Resolved Incidents”. All the resolved problems are listed here with the time stamp and the date. Make sure that Skype services are normal. 2017-10-9 Important Note: There are already many better alternatives to video conferencing and remote working on Mac than Skype For Business. We recommend checking out GoToMeeting for video conferencing and also our guide to the best remote working software for Mac first. It was a long time in coming but you can now finally download Skype For Business For Mac. Although not officially a Skype for Business server per say, but often asked about, the WAC server has its own unique certificate requirements. Sims 4 maxis match default eyes. The WAC certificate must have the subject name and SAN of the internal FQDN of the server itself and not the public FQDN that may be assigned from external sources. Select Install or Update Skype for Business (Lync) Server System. Select the Run Again option on the Step 3: Request, Install or Assign Certificates page. In the Certificate Wizard window, select Edge Internal, and then click Request. Click Next on Request a certificate for the Edge internal (Edge internal) Skype for Business Server usages page.
* Skype for Business 2016 (any version, including latest in the insider 'Fast Ring' releases)
* Macbook Pro - Early 2011
* OS X 'El Capitan' - v10.11.6
* Corporate domain is on Azure AD (Active Directory)
* When signing in with the AD account, you are either a) Given a choice between 'Work or school account' or 'Personal account), b) usually automatically redirected to the company branded signon page.
If that matches up, the next step is to check the certificate which is on domain's federation services (ADFS) host. This may require getting IT involved to find it, or reviewing the SfB logs.
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When you get the host name, for example, 'adfs.mycompany.com', go to that address via HTTPS in Safari. So you'd go to 'https://adfs.mycompany.com'. Once there, click on the lock to the left of the address in the address bar and click the 'Show Certificate' button. Make sure that the selected certificate, in the tree view at the top, is the bottom-most one. The bottom pane should show some brief certificate info (Issued by, Expires, 'This certificate is valid' type message, etc.). Expand the 'Details' section in that lower pane, and look for the 'Signature Algorithm' line, which should be, roughly, the 12th one down. If on that line, you have something similar to 'SHA-512 with RSA Encryption' (forget about the long number afterward), then that is the source of the issue with logging on, and also, activating Office 365 (if you have a company account for it).
OS X prior to 10.12 (Sierra) does not *natively* support 512 bit certificate signatures. So while browsers and everything else shows that, yes, the certificate is good, valid, unexpired, etc, the low level network stack in OSX, which is used by SfB to initially connect, does not, so it cannot validate that the certificate is valid, thus causing this issue.
Unfortunately, at this time, there doesn't appear to be a way to wedge in support for 512 algorithms in OSX, and that includes forcibly upgrading/linking openssl. The only way I've found to date, to use SfB on anything less than 10.12.x, is to essentially MITM yourself, using a proxy application, such as Charles, which will create its own fake certificate which you must trust, to connect.
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I apologize for such a long writeup, but given that despite my hours and hours and hours spent over months of researching the issue, I hope to provide as much useful and helpful information as possible for any future Googlers/Bingers/DuckDuckGoers/etc.