Problem with autodiscover and IMAP on exchange 2019

Question

Problem with autodiscover and IMAP on exchange 2019

drClays 151

Hi,
I have a problem with correctly working autodiscover on my exchange servers.

This is my configuration:

Domain name(external/internal): contoso.com
I have an SSL wildcard certificate: *.contoso.com
External IP addresses:

1.1.1.1,
2.2.2.2
Exchange Servers:
EXCH19A - 10.0.0.10
EXCH19A - 10.0.0.20
EXCH19B - 10.0.1.10
EXCH19B - 10.0.1.20

External DNS:

mail.contoso.com > A > 1.1.1.1
mail.contoso.com > A > 2.2.2.2
autodiscover.contoso.com > A > 1.1.1.1
autodiscover.contoso.com > A > 2.2.2.2

Internal DNS:

mail.contoso.com > 10.0.0.10
mail.contoso.com > 10.0.1.10
autodiscover.contoso.com > 10.0.0.10
autodiscover.contoso.com > 10.0.1.10

These servers working in cluster:
DNS: dag>10.0.0.20\ dag>10.0.1.20

Here is the result from testconnectivity:
266284-test-autodiscover.txt

Here are port redirections on my firewall:

The second problem is with IMAP configuration. IMAP is enabled. Some mailboxes don't synchronize correctly on outlook.
For example: I see other emails in Outlook with Exchange protocol configuration and other emails in Outlook with IMAP protocol configuration on the same mailbox

Any suggestions? In the beginning, I would like to repair autodiscover.

LilyLi2-MSFT 1,981 Reputation points

2022-12-02T07:29:14.9+00:00

Hi @drClays ,

I noticed that your testconnectivity is about Exchange ActiveSync. Do you mean only Autodiscover for mobile devices stopped working? Are Outlook and OWA working fine?

Besides, here is a similar question to yours, you could refer to: the-microsoft-connectivity-analyzer-failed-to-obtain-an-autodiscover-xml-response
Please check if SharedWebConfig.config is missing? And check the IIS binding.

Thanks.
LilyLi2-MSFT 1,981 Reputation points

2022-12-06T04:33:21.703+00:00

Hi,
Please let us know if you would like further assistance.
If you have any update about this issue, please feel free to post back.
Have a nice day!
drClays 151 Reputation points

2022-12-06T10:49:00.907+00:00

Hi @LilyLi2-MSFT ,
Yes, yes, I still have a problem.

When I trying to configure Outlook for new user and I writing email address in fill the program trying to used IMAP protocol:

When I change to advanced settings and choose Exchange protocol that finished correctly but a few moments later showing this popup and "Sign in" to O365... I cannot understand it:

This popup asking about tuser@keyman .com where SAMA is: test.user and mailbox SMTP: test.user@keyman .com

And asking about O365 Sign in:

2 answers

Your answer

LilyLi2-MSFT 1,981 Reputation points

2022-12-02T07:29:14.9+00:00

Hi @drClays ,

I noticed that your testconnectivity is about Exchange ActiveSync. Do you mean only Autodiscover for mobile devices stopped working? Are Outlook and OWA working fine?

Besides, here is a similar question to yours, you could refer to: the-microsoft-connectivity-analyzer-failed-to-obtain-an-autodiscover-xml-response
Please check if SharedWebConfig.config is missing? And check the IIS binding.

Thanks.
LilyLi2-MSFT 1,981 Reputation points

2022-12-06T04:33:21.703+00:00

Hi,
Please let us know if you would like further assistance.
If you have any update about this issue, please feel free to post back.
Have a nice day!
drClays 151 Reputation points

2022-12-06T10:49:00.907+00:00

Hi @LilyLi2-MSFT ,
Yes, yes, I still have a problem.

When I trying to configure Outlook for new user and I writing email address in fill the program trying to used IMAP protocol:

When I change to advanced settings and choose Exchange protocol that finished correctly but a few moments later showing this popup and "Sign in" to O365... I cannot understand it:

This popup asking about tuser@keyman .com where SAMA is: test.user and mailbox SMTP: test.user@keyman .com

And asking about O365 Sign in:

Answer 1

drClays 151

Hi,

I did a few tests on testconnectivity and that looks nice, but on every test, I have the same information about certificate validation:

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.

Outlook test:

ActiveSync test:

SMTP test:

IMAP test:

I can configure my mailbox on Outlook Mobile via exchange protocol and it's working - send/receive email but I cannot do this on external Outlook.

I cannot configure the same account via IMAP protocol on Outlook Mobile, Outlook and Thunderbird. Where I use ports 993/465.

Any suggestions?

LilyLi2-MSFT 1,981 Reputation points

2022-12-09T09:21:45.957+00:00

Hi @drClays ,

I am currently doing some research on this issue and will inform you as soon as possible.
Please be patient for a while.

Thanks for your understanding and support.
LilyLi2-MSFT 1,981 Reputation points

2022-12-12T09:52:09.257+00:00
Hi @drClays ,

Sorry for the late reply.

”When I trying to configure Outlook for new user and I writing email address in fill the program trying to used IMAP protocol.“
That is because Microsoft launched the “Direct Connect to Office365 Feature". You could bypass the 365 connection using the following steps:

Start Registry Editor.

Locate and then select the following registry subkey:
HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\AutoDiscover

Create a DWORD (30-bit) value for ExcludeExplicitO365Endpoint and change the value to “1” to enable it.

For details, please refer tooutlook-issue-with-direct-connect-to-office365-352dd29de65
Please Note: Since these web sites are not hosted by Microsoft, the links may change without notice. Microsoft does not guarantee the accuracy of this information.

”I cannot configure the same account via IMAP protocol on Outlook Mobile, Outlook and Thunderbird.“
Is it possible to configure an account using IMAP protocol on the Outlook client?
If there is no problem on Outlook client, you could set up IMAP account on Outlook Mobile according to this article.

Thanks.
drClays 151 Reputation points

2022-12-12T15:20:40.743+00:00

I have a freak problem with mailbox on mobile phone via exchange protocol.

When I add new mailbox - test.user to Outlook mobile they sync emails. I can receive and send emails. But when I connect to Outlook Mobile old mailbox where are a lot of emails, then Outlook Mobile doesn't synchronizing emails. Can't download emails on my device and I can't send emails.
LilyLi2-MSFT 1,981 Reputation points

2022-12-19T09:21:27.4+00:00
Hi,
Sorry for the late reply.

To resolve the issue more accurately, would you help collect the following information:

Are all old mailboxes unable to sync/download/send emails?

Have you tried adding the mailbox on another device?

Are there any detailed errors occurring?

Answer 2

Hi,
This is probably a problem with one mailbox. I tried it on other devices and there is the same problem.

Now I try to fix the failover cluster of dag.

There was on Exchange servers only one ethernet adapter with two IP addresses.

I add a new eth adapter and configure the second IP from eth1 on eth2.

Now I have:
EXCH19A:
ETH1: 10.0.0.10/27
ETH2: 10.0.0.20/27

EXCH19B:
ETH1: 10.0.1.10
ETH2: 10.0.1.20

When I added new eth adapters I see a lot of new ReplicationDagNetwork and I think it's something wrong.
I would like to change network on 192.168.x.x for replication - is it's gonna be ok?

In ECP/Servers/DAG where is configured witness, there are IP addresses:
10.0.0.10
10.0.1.20
and it's wrong.

In AD I have a computer object colled "DAG01" and in DNS record A has DAG01.contoso.com with IP: 10.0.0.10 and it's wrong

Witness is:
EXWitness with IP: 10.0.1.60

Now I would like to change DNS record A "DAG01" from 10.0.0.10 to 10.0.1.70.
Next step when I change DNS I would like to change IP DAG on ECP. I will remove 10.0.0.10 and 10.0.1.20 and add only 10.0.1.70 and it's could be fine, yes?

How to fix EVENT ID 1259?

Cluster network name resource failed registration of one or more associated DNS name(s) because the cluster service failed clean up the existing records corresponding to the network name.

Cluster Network name: 'Claster name'
DNS Zone: 'contoso.com'

Ensure that cluster name object (CNO) is granted permissions to the Secure DNS Zone.

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Problem with autodiscover and IMAP on exchange 2019

2 answers

Your answer