Hello, We have several users reporting the message 'A secure connection cannot be established with the server outlook.office365.com. Do you want to continue?' When they start up Mac Outlook 2016. It doesn't happen every time, and it doesn't happen for all users. We're all on the most recent Mac Outlook 2016 (15.34) and are accessing email through our Office 365 tenant. For now, we have been clicking 'Continue' to allow work to continue. An in-depth discussion of the distinction between authentication and authorization including the principles and definitions of both and the implications to identity management in the big picture. 'Microsoft Outlook wants to use your confidential information stored in 'Microsoft Identity xxxxxx-xxxxx-xxxxx-xxxxxxx' in your keychain' To allow this, enter the login keychain password but I have to set to use automatically and when I try to view it I cannot access the area. However, users are less than comfortable when they see tis dialog. I've attached a picture of the dialog below. Has anybody else seen this happen with Mac Outlook 2016 and their Office 365 tenant? Hi Steve, Based on my research, the warning message is typically caused by your web server for your domain name returning the incorrect certificate for your website. To resolve this issue, we can use one of the following methods: Method 1: Reissue a certificate that includes the domain name as the Subject Alternative Name. This enables you to resolve the issue for all Outlook for Mac clients without having to trust the certificate from each client individually. Method 2: Trust the certificate on the Mac client. This solution enables you to resolve the issue quickly for individual Mac clients without having to reissue the certificate. When you receive the certificate warning message, click Show Certificate. Microsft office for mac cheap discount. Select the Always trust when connecting to check box, and then click Continue: For more information about the warning message, please read the following article: Hope you can find this helpful. Best regards, Yuki Sun Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact. While that's a similar issue, it doesn't appear to be what's causing the problem we're seeing. There are several key differences: 1) Our problem is intermittent. Any specific user will see the problem a couple of times in one day, and then not for several days. They'll think the problem is gone, and then it will appear once or twice again. Actual certificate problems will cause an error every time the Outlook client is started. 2) The certificate reports as valid. It doesn't say there is a name mismatch, like in the error described in the support article. 3) We are connecting to an Exchange server in Office 365. It's not our server.it's Microsoft's server. We don't have any control over the certificates that they install on the server. Thus, we can't re-issue any certificates. We have no choice but to keep monitoring the problem and hope that we can find some additional information that will help us troubleshoot the cause. Thanks for your help. Hi Yuki, NO it does not solve the problem. This seems to be a MICROSOFT-owned problem, because the target domain in question is owned by Microsoft (outlook.office365.com) Is one of the servers in that cluster compromised or misconfigured?
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