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Hello Brett F,
Thanks for the post in the forum.
Can you visit the tool site www.testexchangeconnectivity.com and switch to the office 365 tab and under the Microsoft Office Outlook Connectivity tests
run the Outlook Anywhere (RPC over Http) test. Run the test using autodiscover to discover setting. Use your Offrice 365 mailbox info.
The email address and the Microsoft Online login ID are the same. Please post the results of that log that it generates from the test.
We will use these results to determine why OOO settings are not working in Outlook.
Ok as follows, one error I will post URL below info...
Testing RPC/HTTP connectivity.
The RPC/HTTP test completed successfully.
Attempting to resolve the host name bl2prd0410.outlook.com in DNS.
The host name resolved successfully.
IP addresses returned: 18.104.22.168
Testing TCP port 443 on host bl2prd0410.outlook.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.
ExRCA is attempting to obtain the SSL certificate from remote server bl2prd0410.outlook.com on port 443.
ExRCA successfully obtained the remote SSL certificate.
Remote Certificate Subject: CN=outlook.com, OU=Exchange, O=Microsoft Corporation, L=Redmond, S=Washington, C=US, Issuer: CN=Microsoft Secure Server Authority, DC=redmond, DC=corp, DC=microsoft, DC=com.
Validating the certificate name.
The certificate name was validated successfully.
Host name bl2prd0410.outlook.com was found in the Certificate Subject Alternative Name entry.
Certificate trust is being validated.
The certificate is trusted and all certificates are present in the chain.
ExRCA is attempting to build certificate chains for certificate CN=outlook.com, OU=Exchange, O=Microsoft Corporation, L=Redmond, S=Washington, C=US.
One or more certificate chains were constructed successfully.
A total of 1 chains were built. The highest quality chain ends in root certificate CN=GTE CyberTrust Global Root, OU="GTE CyberTrust Solutions, Inc.", O=GTE Corporation, C=US.
Analyzing the certificate chains for compatibility problems with versions of Windows.
No Windows compatibility problems were identified.
The certificate chain has been validated up to a trusted root. Root = CN=GTE CyberTrust Global Root, OU="GTE CyberTrust Solutions, Inc.", O=GTE Corporation, C=US.
Testing the certificate date to confirm the certificate is valid.
Date validation passed. The certificate hasn't expired.
The certificate is valid. NotBefore = 4/17/2012 9:26:21 PM, NotAfter = 4/17/2014 9:26:21 PM
Checking the IIS configuration for client certificate authentication.
Client certificate authentication wasn't detected.
Accept/Require Client Certificates isn't configured.
Testing HTTP Authentication Methods for URL bl2prd0410.outlook.com/.../rpcproxy.dll.
The HTTP authentication methods are correct.
ExRCA found all expected authentication methods and no disallowed methods. Methods found: Basic
Testing SSL mutual authentication with the RPC proxy server.
Mutual authentication was verified successfully.
Certificate common name outlook.com matches msstd:outlook.com.
Attempting to ping RPC proxy bl2prd0410.outlook.com.
RPC Proxy was pinged successfully.
Completed with HTTP status 200 - OK
Attempting to ping RPC endpoint 6001 (Exchange Information Store) on server bl2prd0410.mailbox.outlook.com.
The endpoint was pinged successfully.
RPC Status Ok (0) returned in 842 ms.
Testing the Name Service Provider Interface (NSPI) on the Exchange Mailbox server.
The NSPI interface was tested successfully.
Attempting to ping RPC endpoint 6004 (NSPI Proxy Interface) on server bl2prd0410.mailbox.outlook.com.
RPC Status Ok (0) returned in 30 ms.
Testing NSPI "Check Name" for user email@example.com against server bl2prd0410.mailbox.outlook.com.
The test passed with some warnings encountered. Please expand the additional details.
Tell me more about this issue and how to resolve it
NspiBind returned ecNotSupported. This typically indicates that your server requires RPC encryption. ExRCA will attempt the NSPI test again with encryption.
Check Name succeeded.
DisplayName: Finch, Brett, LegDN: /o=ExchangeLabs/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=22cf4daed44a4bf592cf25d2ee26bdb1-bfinch_06152884ce
Testing the Referral service on the Exchange Mailbox server.
The Referral service was tested successfully.
Attempting to ping RPC endpoint 6002 (Referral Interface) on server bl2prd0410.mailbox.outlook.com.
RPC Status Ok (0) returned in 186 ms.
Attempting to perform referral for user /o=ExchangeLabs/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=22cf4daed44a4bf592cf25d2ee26bdb1-bfinch_06152884ce on server bl2prd0410.mailbox.outlook.com.
ExRCA successfully got the referral.
The server returned by the Referral service: BL2PRD0410.mailbox.outlook.com
Testing the Exchange Information Store on the Mailbox server.
ExRCA successfully tested the Information Store.
RPC Status Ok (0) returned in 140 ms.
Attempting to log on to the Exchange Information Store.
ExRCA successfully logged on to the Information Store.
The one error
Connectivity Test Successful with Warnings
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Hello Brett F,
I suggest you try this:
While Outlook is running, click the CTRL key and then right-click the Outlook icon in the system tray and then select “Test Email Autoconfiguration”.
2. Confirm that your email address is in the address field; uncheck “Use Guessmart” and “secure Guessmartauthentication” boxes. Then click the “Test” button.
3. Once it runs, capture a screen shot of the Log tab and Results tab.
If autodiscover does not work, please refer to the following article to deploy the autodiscover service between the AD forests:
If you have additional questions or concerns feel free to post on the forum.
I was quite shocked to learn of the depenancy of autodiscover as we are manually configuring clients at this time. I have made an addditional ALIAS to Outlook.com's CN and it seems to be working now. That is a bug / has to be fixed. In a hybrid /on-premise / cloud solution, the OOO cannot be dependant on a DNS entry, that is just silly.
1 out of 1 people found this post helpful.
Glad to hear that your question was answered. I will now close this thread. If you have other questions, please feel free to post on the forum. It's always our pleasure to assist.