We are using exchange 2016. Mac users keeps on disconnecting on exchange using mac mail. The issue is reported to Microsoft.
Below is a summary of the case.
Symptom: MacBook apple mail always disconnect on exchange server
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Cause: Autodiscover process not correctly handle by MacBook
- Checked that all server components and services were ok
- Checked that the mail flow was ok
- Checked on IIS Default Web Site and Back End Site have the correct bindings and certificates assigned (Default: Public Certificate, BackEnd: Microsoft Exchange Certificate).
- Checked authentication and other settings on the EWS Virtual Directory, since MacBook will use this VD to connect to Exchange but was everything ok
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- Customer confirmed that Outlook clients, mobile devices and OWA are working correctly.
- Recreated the issue by removing the profile on the Macbook and create a new one, and checked that was not able to correctly configured, and was presenting a Self-Signed Certificate, not the Public one.
- Testing on our MacBook but is getting a wrong certificate: Remote Certificate Subject: CN=sl17.sahara.net.sa, OU=PositiveSSL, OU=Domain Control Validated, Issuer: CN='cPanel, Inc. Certification Authority', O='cPanel, Inc.', L=Houston, S=TX, C=US
-Testing on ExRCA allowing automatic configuration using Autodiscover ended up with error when sync
-Testing on ExRCA manually selection the EWS website, perform all steps successfully (because we are bypassing the autodiscover, providing directly the rootdomain test of Autodiscover)
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-Showed on ExRCA that the first certificate was not the correctly one and the MAC was stuck on the first step of the Autodiscover
- This will also affect the MacBook that will try to connect using IMAP
-Outlook clients, will eventually connect because, they will first attempt to connect to https://domain.com.sa/autodiscover/autodiscover.xml and next step will be: https://autodiscover.domain.com.sa/autodiscover/autodiscover.xml . However, Mac users stuck on the first process., taking the wrong certificate.
- For Windows machines we can avoid that behavior but that is not possible on Mac I am afraid.
- Unfortunately, It is well known that Mac products are not working 100% with Microsoft products such us Exchange, ActiveSync issues, Autodiscover issues among others.
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MacBook Pro, OS X Yosemite (10.10.5)