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Exchange 2019 - IMAP Sync Failure

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Les

I have just deployed a new instance of Exchange 2019. Active Sync works fine (outlook and owa) and mail is processed ingress/egress fine. After enabling the IMAP services and associating the self signed certificate with the IMAP service, I fail to sync successfully from outlook client on MacOS.

[Configuration Info]

InternalConnectionSettings : {myMailServer.fqdn:993:SSL, myMailServer.fqdn:143:TLS}

Status Name DisplayName

Running MSExchangeIMAP4 Microsoft Exchange IMAP4 Running MSExchangeIMAP4BE Microsoft Exchange IMAP4 Backend

[Mail Client Settings] Incoming server: myMailServer.fqdn:993 (Use SSL to connect) Outgoing server: myMailServer.fqdn:587 (Use SSL to connect)

[ECP Receive Connector Configuration] Client Frontend Authentication Settings

  • Transport Layer Security - enabled
  • Basic Authentication - enabled
  • Integrated Windows authentication - enabled
  • Exchange Server authentication Permission Groups
  • Exchange users - enabled
  • Anonymous users - enabled

Scope

  • both IPv4 and IPv6 - left defaults unchanged
  • port 587 - default unchanged for IPv4 and IPv6

Not quiet sure why the client can connect to the exchange server with the IMAP settings but not sync inbound email or send an email (sitting in outbox). I could not see anything obvious in the event logs or logs in the exchange installation path. Any suggestions you could offer in troubleshooting this would be appreciated.

Best regards - Les

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Ivan_Wang avatar
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Ivan_Wang
1. Could you see any new emails go into your mailbox if you access mailbox without IMAP? 2. What happens if you click the **Send/Receive All** Folders or **Update Folder** button? 3. What about other clients with IMAP4? 4. When did you encounter this issue? External access or internal access? Besides, I think you can perform an EXRAC(**https://testconnectivity.microsoft.com/tests/Imap/input**) to see if there is any error during the IMAP4 connectivity test.
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Ivan_Wang avatar
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Ivan_Wang
Here is a microsoft docs about this similar issue, please check if it helps: https://support.microsoft.com/en-us/office/i-can-t-send-or-receive-messages-in-outlook-for-mac-2d123bee-676c-4279-bce2-9b4c2da1e8f5
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Ivan_Wang avatar
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Ivan_Wang
Hi, any update?
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Les avatar
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Les
Hello Ivan_Wang, I could not get this to work with Outlook 'new' and I came across different discussions on this topic with statements that the IMAP support was in experimental phase (how true that is remains to be verified). What I have verified since however, is that IMAP works just fine with windows mail app in addition to the MacOS mail app. These two apps have zero problem with the configuration, which would indicate that the implementation in Outlook 'new' is the problem. Les
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Ivan_Wang avatar
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Ivan_Wang
Did you try EXRAC on MacOS? Maybe it will tell us something.
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