Outlook for Android, SM V15 + EAS
Problem reported by Paul Blank - 9/3/2020 at 9:21 PM
Submitted
I know SM V15 is out of support, but suddenly Outlook for Android no longer can connect to my SM V15 / EAS account. Throws an error about invalid login name / password. Seems to have happened in the last few days.

Interestingly enough, Nine email for Android (from 9folders.com) continues to work just fine with the same EAS account. And I'm pretty sure that Outlook for Android has changed, not the other way around.

The Microsoft Remote Connectivity Analyzer for Exchange ActiveSync reports this:

(And of course, "Tell me more about this issue and how to resolve it" is not particularly helpful.)

Welcoming any comments / ideas here. Not a huge problem, but would like some insight. BTW have NEVER been able to get Outlook for IOS working with SM+EAS. We've used IMAP or another IOS client instead.

The Microsoft Connectivity Analyzer is testing Exchange ActiveSync.The Exchange ActiveSync test failed.
Test Steps
Attempting to resolve the host name email.[domain].com in DNS.The host name resolved successfully.
Additional Details
Testing TCP port 443 on host email.[domain].com to ensure it's listening and open.The port was opened successfully.
Testing the SSL certificate to make sure it's valid.The certificate passed all validation requirements.
Test Steps
The Microsoft Connectivity Analyzer is probing the TCP endpoint 100.38.5.4 on port 443 to detect which SSL/TLS protocols and cipher suites are enabled.We were able to detect the enabled protocols and cipher suites.
Additional Details
Checking that your server supports TLS protocols and cipher suites that are compatible with Office 365.Your server supports TLS protocols and cipher suites compatible with Office 365.
Additional Details
The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server email.[domain].com on port 443.The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
Additional Details
Validating the certificate name.The certificate name was validated successfully.
Additional Details
Certificate trust is being validated.The certificate is trusted and all certificates are present in the chain.
Test Steps
The Microsoft Connectivity Analyzer is attempting to build certificate chains for certificate CN=email.[domain], OU=PositiveSSL, OU=Domain Control Validated.One or more certificate chains were constructed successfully.
Additional Details
Analyzing the certificate chains for compatibility problems with versions of Windows.The test passed with some warnings encountered. Please expand the additional details.
Additional Details
The Microsoft Connectivity Analyzer can only validate the certificate chain using the Root Certificate Update functionality from Windows Update. Your certificate may not be trusted on Windows if the "Update Root Certificates" feature isn't enabled.
Testing the certificate date to confirm the certificate is valid.Date validation passed. The certificate hasn't expired.
Additional Details
The certificate is valid. NotBefore = 11/9/2019 12:00:00 AM, NotAfter = 11/19/2021 11:59:59 PM
Testing HTTP Authentication Methods for URL https://email.[domain].com/Microsoft-Server-ActiveSync/.The HTTP authentication test failed.
Additional Details
A 401 error was received from the server, but no authentication methods are supported. HTTP Response Headers: X-UA-Compatible: IE=edge Content-Length: 1293 Cache-Control: private Content-Type: text/html Date: Fri, 04 Sep 2020 04:08:07 GMT Server: Microsoft-IIS/8.5 X-AspNet-Version: 4.0.30319 X-Powered-By: ASP.NET 





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Duarte Replied
We are also noticing intermittent anomalies in Outlook for Android, but in the latest version of SM.

TLS v1.0 active on the server could be the problem for Outlook for Android.

Although protocol versions v1.1 and 1.2 are also available in our case, it seems that Outlook penalizes or has a bug when the mail server has the TLS v1.0 protocol active.

We are afraid to disable the TLS v1.0 protocol due to incompatibilities that may arise with older mail clients (or in SMTP communication with older mail servers) where this is the "most recent" available protocol.

We still don't have enough feedback to reach a conclusion.
 
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Paul Blank Replied
"My" few remaining Outlook for Android users - including myself - have been successfully switched to Nine. Nine is inexpensive enough; LOTS cheaper than wasting my time troubleshooting. Problem solved. 

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