There Was A Problem Verifying The Certificate From The Server Skype For Business Mac

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Apr 04, 2019 Note: Skype for Business on Mac gets represented by the underlying ADAL library as user agent Mozilla/5.0 (no option to set it from the app), and Windows Integrated Authentication is generally used only for Windows clients and therefore not supported by ADAL library on Mac. 'There was a problem verifying the certificate server. Check your device's clock setting, or contact your support team.' I have removed the SfBfM-related files from /Library, reinstalled Skype and (what I think are the proper) certificates for our server.

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):

* 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.

When you get the host name, for example, '', go to that address via HTTPS in Safari. So you'd go to ''. 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.

Skype For Business Mac Error There Was A Problem Verifying The Certificate From The Server

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.

Jul 13, 2017 8:50 AM

Sometimes, you might face an error message which says “Skype certificate error has occurred” when you try to log in to Skype for Lync online. Most of the times, you will find the problem in the Lync 2010 and 2013 versions respectively. Due to this error message, you would be unable to access your Lync account. In addition, you might get the problem you try to log in with the personal certificate while signing to your account. Additionally, the error message while trying to sign-in to your account and make your account error-free.

If you are struggling with the same situation and are trying to get some information about the possible fixes in order to fix the issue. Hence, follow the article thoroughly and you will able to fix the issue without any difficulties. So, stay tuned with this context and apply the discussed process as described in the section below:

Prime Reasons behind Skype Certificate Error

Before going to the solution section, you need a clear idea of how this Skype certificate error

Occurs. When you analyze the causes for this particular issue, you find a multiple of reasons responsible for this. However, the main reason is that the software is out of date. Moreover, the Lync client is also responsible for this particular issue. Apart from this, an outdated Microsoft Online Service also causes the problem. In addition, the cached certifications of Skype might be outdated or the program may be damaged due to malware attack.

Hence, once you figure out why this error message came out, now let’s proceed with the solutions section.

Effective Hacks to Fix Skype Certificate Error

Here, in this particular section, we have provided you with proven techniques to fix Skype certificate error with ease. Hence, take a look at the solutions, read them, and apply them in order to get rid of this situation:

Fix 1: Uninstall and Reinstall the Skype Application

When you confront the glitches, the basic and easy method that you can try in order to resolve the issue. To do so, work your way through the following section:


Step 1

At the beginning of the process, you need to move to the search panel and type Settings in the search bar. Then, press the Enter button to open it up.

Step 2

In the Settings option, go to the Programs and features section, double-click on it to expand the option. Here, you will find all the applications that are installed on your device.

Step 3

Then, search for the Skype application and right-click on it. From the dropdown list, select the Uninstall option and press OK to confirm the action.

Step 4

Meanwhile, the uninstallation process will begin. Once the process is done, restart the system. After that, open the system and launch a web browser to download the application again from the official website of Skype.

Step 5

Download the new version of the Skype application and install it on your device. Follow the instructions properly to finish the installation process. Thereafter, launch the application, enter the username and password to sign in to your Skype account.

After completing the process successfully, check whether the certificate error is there or not. Otherwise, move to the next section.

Fix 2: Update the Skype Application

An outdated version of Skype is also lead you in this situation. Hence, you an updated version in order to fix the issue. It is better to turn on the automatic updates on Skype. But if you disable that section, follow the steps given below and get the fresh version of Skype.

  1. At first, start the Skype application on your computer. After that, move to the Menu bar and click on the help button to open up the drop-down menu list.
  2. Thereafter, press the Check for Updates option from the list. If an updated version is available, click on the download option. It will automatically download the latest version. After getting the latest version of the Skype application, restart the system and check whether the problem gets resolved. To keep the application updated, you need to turn the automatic update option.

To enable the option, apply the steps as described in the section below.

  1. At first, launch the Skype application and go to the Menu bar section. After that, select the Tools option.
  2. In that section, select the Options button. Now, let’s move to the Advanced section which is available in the left side panel. Then select the Automatic Updates option. Turn on the section and click Save to apply the change.

Fix 3: Remove Personal Certificate and Reinstall

In order to resolve the Skype certificate error, you need to delete the personal certificate and install it again. Hence, do the following steps to get rid of this situation:

There Was A Problem Verifying The Certificate From The Server Skype For Business Mac Os

  • Firstly, open the Run window by pressing the Windows key and R at the same time. Then, type certmgr.msc in the Run box and press the Enter button. It will open the Windows Certificate Manager option.
  • Now, expand the Personal folder by pressing the Certificate option. Next, search for the Communication Server certificate. Find out the needed the certificate is present or not. If yes, then check it did not expire.
  • Lastly, delete the Communication server certificate and try to sign in to your Skype account for the business purposes.

Fix 4: Turn the Antivirus off

If the above solutions fail to solve the issue, then try this one. Virus attack might damage the Skype application and as a result, you will get the certificate error. Hence, to resolve the glitches, you need to disable the antivirus program and check the error still persists or not.

  1. To begin the process, open the Run dialog box and type control on the Run box. After that, hit the Enter button to open the Control Panel on your device.
  2. In the Control Panel option locate the search box and type Firewall. When the search result came out, expand the Firewall application. Simply tick a right mark on the right box next to Turn Windows Firewall off section. Do the same procedure for Public and Private network option to disable it. Click the Save button to apply the changes.

Concluding Note

Ending this article, you can follow this article in order to fix Skype certificate error without any difficulties. Also, the mentioned methods are simple, easy and hassle-free. In case, if you still facing the same error message while using the Skype application, you can get in touch with us through our comment section below.