Outlook 2016 MAC not syncing/pushing with Zimbra w EWS

Hello Community,

I installed Outlook 2016 for MAC and configured my Zimbra account as an exchange account to my Zimbra server which is running EWS.

Status:

My entire mailbox/calendar/contacts successfully downloaded into Outlook over MAPI/Microsoft ActiveSync

I can send and receive emails*

Problem:

When emails come in or I update a calendar item on my Blackberry, they are not sync'd or pushed from Zimbra/EWS to my Outlook client. I see my phone blink that there is a new email and I need to click "Send & Receive" in order for the Outlook client to sync.

Test:

Email is sent to this account.

Result: Does not show up in Outlook automatically, requires manual intervention (Send & Receive) to be pressed.

Ive used Outlook and Exchange and Zimbra for years and never had this problem. Why is it not Syncing/pushing?

Logs

Normal chatter between Outlook Client and Zimbra/EWS:

tail -f  microsoft\ outlook-20160127-1539a.log

01/27/2016 16:05:01.325    OUTLOOK (0x2f5)    0xb0081000    Outlook    outlook.network    ibn0j    Verbose    {"Details": "Request 0x7c560340 on CHttpConnection 0x7db07d6c, Host: zimbra.xmission.com, Port: 443, SSL: 1, StdAuth: 0; RS:LOADING"}

01/27/2016 16:05:01.325    OUTLOOK (0x2f5)    0xb0081000    Outlook    http.request    ibsbd    Verbose    HttpRequest::SendRequestInternal {"RequestID": "0x7c560340.1453939501", "ConnectionID": "0x7de194c0.1453938789", "PreAuth": true, "RetryCount": 3, "Result.value": 0, "Result.extvalue": 0}

01/27/2016 16:05:01.325    OUTLOOK (0x2f5)    0xb0081000    Outlook    http.request    ibsbe    Verbose    HttpRequest::SendRequestInternal {"RequestID": "0x7c560340.1453939501", "ResponseHttpStatus": 200, "AuthenticationScheme": 0, "AuthSchemesResult": 0}

01/27/2016 16:05:01.326    OUTLOOK (0x2f5)    0xb0081000    Outlook    http.request    ibct1    Verbose    Calling sink on request state changed {"RequestID": "0x7c560340.1453939501", "RequestState": "onResponseReceived", "ErrorCode": 0}

01/27/2016 16:05:01.326    OUTLOOK (0x2f5)    0xb0081000    Outlook    outlook.network    ibn0j    Verbose    {"Details": "Request 0x7c560340 on CHttpConnection 0x7db07d6c, Host: zimbra.xmission.com, Port: 443, SSL: 1, StdAuth: 0; RS:DONE"}

01/27/2016 16:05:01.326    OUTLOOK (0x2f5)    0xb0081000    Outlook    http.request    ibyhm    Verbose    Sending request is done. {"RequestID": "0x7c560340.1453939501", "RequestTimedOut": false, "Result.value": 0, "Result.extvalue": 0, "RequestAborted": false}

01/27/2016 16:05:01.326    OUTLOOK (0x2f5)    0xb0081000    Outlook    http.request    ibyhh    Verbose    Getting response header. {"RequestID": "0x7c560340.1453939501", "ResponseHeader": "request-id"}

01/27/2016 16:05:01.326    OUTLOOK (0x2f5)    0xb0081000    Outlook    outlook.exchange.ews    ibnfe    Verbose    EWS: Received response {"Connection": "0x7DB07D6C", "Status": 200, "ClientRequestID": "8F5690E8-F0E9-487B-8EBE-D615088EC10B", "ServerRequestId": null}

01/27/2016 16:05:01.326    OUTLOOK (0x2f5)    0xb0081000    Outlook    outlook.exchange.ews    ib3zl    Verbose    EWS: Response data received {"Thread": "0x79887FB0", "Data": "<soap:Envelope xmlns:soap="http://schemas.xmlsoap.org/soap/envelope/"><soap:Header><ns2:ServerVersionInfo xmlns:ns2="http://schemas.microsoft.com/exchange/services/2006/types" xmlns="http://schemas.microsoft.com/exchange/services/2006/messages" MajorVersion="14" MinorVersion="3" MajorBuildNumber="158" MinorBuildNumber="11" Version="Exchange2010_SP2"/></soap:Header><soap:Body><SubscribeResponse xmlns="http://schemas.microsoft.com/exchange/services/2006/messages" xmlns:ns2="http://schemas.microsoft.com/exchange/services/2006/types"><ResponseMessages><SubscribeResponseMessage ResponseClass="Success"><MessageText>Message not supported.</MessageText><ResponseCode>NoError</ResponseCode></SubscribeResponseMessage></ResponseMessages></SubscribeResponse></soap:Body></soap:Envelope>"}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    outlook.exchange.ews    ib3zm    Verbose    EWS Request {"ClientRequestID": "10F57634-4B43-4861-9500-72EA12075A4B", "Request XML": "<?xml version="1.0" encoding="UTF-8"?><soap:Envelope xmlns:soap="http://schemas.xmlsoap.org/soap/envelope/" xmlns:t="http://schemas.microsoft.com/exchange/services/2006/types" xmlns:m="http://schemas.microsoft.com/exchange/services/2006/messages"><soap:Header><t:RequestServerVersion Version="Exchange2010_SP1" /><t:MailboxCulture>en-US</t:MailboxCulture><t:TimeZoneContext><t:TimeZoneDefinition Id="Pacific Standard Time"/></t:TimeZoneContext></soap:Header><soap:Body><Subscribe xmlns="http://schemas.microsoft.com/exchange/services/2006/messages"><StreamingSubscriptionRequest SubscribeToAllFolders="true"><t:EventTypes><t:EventType>CopiedEvent</t:EventType><t:EventType>CreatedEvent</t:EventType><t:EventType>DeletedEvent</t:EventType><t:EventType>ModifiedEvent</t:EventType><t:EventType>MovedEvent</t:EventType></t:EventTypes></StreamingSubscriptionRequest></Subscribe>"}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibyhf    Verbose    Http open request {"RequestID": "0x7bc6f910.1453939519", "RequestMethod": "POST", "AsyncRequest": false}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibyhg    Verbose    Setting request header. {"RequestID": "0x7bc6f910.1453939519", "RequestHeader": "User-Agent"}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibyhg    Verbose    Setting request header. {"RequestID": "0x7bc6f910.1453939519", "RequestHeader": "Accept-Language"}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibyhg    Verbose    Setting request header. {"RequestID": "0x7bc6f910.1453939519", "RequestHeader": "Content-Type"}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibyhg    Verbose    Setting request header. {"RequestID": "0x7bc6f910.1453939519", "RequestHeader": "X-ClientStatistics"}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibyhg    Verbose    Setting request header. {"RequestID": "0x7bc6f910.1453939519", "RequestHeader": "Client-Request-Id"}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibyhg    Verbose    Setting request header. {"RequestID": "0x7bc6f910.1453939519", "RequestHeader": "SOAPAction"}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    outlook.exchange.ews    ibnfd    Verbose    EWS: Sending request {"Connection": "0x7CA1840C", "URL": "/ews/Exchange.asmx", "SoapAction": ""http://schemas.microsoft.com/exchange/services/2006/messages/Subscribe"", "ClientRequestID": "10F57634-4B43-4861-9500-72EA12075A4B"}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibyho    Verbose    Sending Stream. {"RequestID": "0x7bc6f910.1453939519"}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    outlook.network    ibsa5    Verbose    CAuthenticationHandler::getEnumerator {"CachedRequest": true, "HttpStatus": 0, "AuthScheme": 0}

01/27/2016 16:05:19.458    OUTLOOK (0x2f5)    0xb029b000    Outlook    outlook.network    ibsa6    Verbose    CAuthenticationHandler GetEnumerator call {"PromptForCreds": false, "NewAuthScheme": 0}

01/27/2016 16:05:19.548    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibct0    Verbose    Calling sink on request state changed {"RequestID": "0x7bc6f910.1453939519", "RequestState": "onHeaderAvailable", "ErrorCode": 0}

01/27/2016 16:05:19.548    OUTLOOK (0x2f5)    0xb029b000    Outlook    outlook.network    ibn0j    Verbose    {"Details": "Request 0x7bc6f910 on CHttpConnection 0x7ca1840c, Host: zimbra.xmission.com, Port: 443, SSL: 1, StdAuth: 0; RS:HEADERS_RECEIVED"}

01/27/2016 16:05:19.548    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibct2    Verbose    Calling sink on request state changed {"RequestID": "0x7bc6f910.1453939519", "RequestState": "onDataAvailable", "ErrorCode": 0}

01/27/2016 16:05:19.548    OUTLOOK (0x2f5)    0xb029b000    Outlook    outlook.network    ibn0j    Verbose    {"Details": "Request 0x7bc6f910 on CHttpConnection 0x7ca1840c, Host: zimbra.xmission.com, Port: 443, SSL: 1, StdAuth: 0; RS:LOADING"}

01/27/2016 16:05:19.548    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibsbd    Verbose    HttpRequest::SendRequestInternal {"RequestID": "0x7bc6f910.1453939519", "ConnectionID": "0x7de194c0.1453938789", "PreAuth": true, "RetryCount": 3, "Result.value": 0, "Result.extvalue": 0}

01/27/2016 16:05:19.548    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibsbe    Verbose    HttpRequest::SendRequestInternal {"RequestID": "0x7bc6f910.1453939519", "ResponseHttpStatus": 200, "AuthenticationScheme": 0, "AuthSchemesResult": 0}

01/27/2016 16:05:19.548    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibct1    Verbose    Calling sink on request state changed {"RequestID": "0x7bc6f910.1453939519", "RequestState": "onResponseReceived", "ErrorCode": 0}

01/27/2016 16:05:19.548    OUTLOOK (0x2f5)    0xb029b000    Outlook    outlook.network    ibn0j    Verbose    {"Details": "Request 0x7bc6f910 on CHttpConnection 0x7ca1840c, Host: zimbra.xmission.com, Port: 443, SSL: 1, StdAuth: 0; RS:DONE"}

01/27/2016 16:05:19.548    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibyhm    Verbose    Sending request is done. {"RequestID": "0x7bc6f910.1453939519", "RequestTimedOut": false, "Result.value": 0, "Result.extvalue": 0, "RequestAborted": false}

01/27/2016 16:05:19.549    OUTLOOK (0x2f5)    0xb029b000    Outlook    http.request    ibyhh    Verbose    Getting response header. {"RequestID": "0x7bc6f910.1453939519", "ResponseHeader": "request-id"}

01/27/2016 16:05:19.549    OUTLOOK (0x2f5)    0xb029b000    Outlook    outlook.exchange.ews    ibnfe    Verbose    EWS: Received response {"Connection": "0x7CA1840C", "Status": 200, "ClientRequestID": "10F57634-4B43-4861-9500-72EA12075A4B", "ServerRequestId": null}

01/27/2016 16:05:19.549    OUTLOOK (0x2f5)    0xb029b000    Outlook    outlook.exchange.ews    ib3zl    Verbose    EWS: Response data received {"Thread": "0x79887FB0", "Data": "<soap:Envelope xmlns:soap="http://schemas.xmlsoap.org/soap/envelope/"><soap:Header><ns2:ServerVersionInfo xmlns:ns2="http://schemas.microsoft.com/exchange/services/2006/types" xmlns="http://schemas.microsoft.com/exchange/services/2006/messages" MajorVersion="14" MinorVersion="3" MajorBuildNumber="158" MinorBuildNumber="11" Version="Exchange2010_SP2"/></soap:Header><soap:Body><SubscribeResponse xmlns="http://schemas.microsoft.com/exchange/services/2006/messages" xmlns:ns2="http://schemas.microsoft.com/exchange/services/2006/types"><ResponseMessages><SubscribeResponseMessage ResponseClass="Success"><MessageText>Message not supported.</MessageText><ResponseCode>NoError</ResponseCode></SubscribeResponseMessage></ResponseMessages></SubscribeResponse></soap:Body></soap:Envelope>"}

Next, I will click "Send & Receive" and I see Outlook sees an update and syncs the databases:

Only providing relevant logs as there are tons when I click "Send & Receive"

01/27/2016 16:08:11.842    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmpd    Verbose    Sync Engine: Starting {"Engine": "Exchange folder Inbox", "Sync Time": "1/27/2016 16:8:11 [218306408]"}

...

01/27/2016 16:08:11.933    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.exchange.ews    ibnfd    Verbose    EWS: Sending request {"Connection": "0x7C55973C", "URL": "/ews/Exchange.asmx", "SoapAction": ""http://schemas.microsoft.com/exchange/services/2006/messages/SyncFolderItems"", "ClientRequestID": "34A7696E-842F-40CD-B203-D4F304EE5FF3"}

... 01/27/2016 16:08:12.299    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.exchange.ews    ib3zl    Verbose    EWS: Response data received {"Thread": "0x7980FEB0", "Data": "<soap:Envelope xmlns:soap="http://schemas.xmlsoap.org/soap/envelope/"><soap:Header><ns2:ServerVersionInfo xmlns:ns2="http://schemas.microsoft.com/exchange/services/2006/types" xmlns="http://schemas.microsoft.com/exchange/services/2006/messages" MajorVersion="14" MinorVersion="3" MajorBuildNumber="158" MinorBuildNumber="11" Version="Exchange2010_SP2"/></soap:Header><soap:Body><SyncFolderItemsResponse xmlns="http://schemas.microsoft.com/exchange/services/2006/messages" xmlns:ns2="http://schemas.microsoft.com/exchange/services/2006/types"><ResponseMessages><SyncFolderItemsResponseMessage ResponseClass="Success"><ResponseCode>NoError</ResponseCode><SyncState>{B24C2E4B-3F1E-38B6-B64D-423347951648}7</SyncState><IncludesLastItemInRange>true</IncludesLastItemInRange><Changes><ns2:Create><ns2:Message><ns2:ItemId Id="94005" ChangeKey="513528"/><ns2:ItemClass>IPM.Note</ns2:ItemClass><ns2:Subject>Welcome to Microsoft Community</ns2:Subject></ns2:Message></ns2:Create></Changes></SyncFolderItemsResponseMessage></ResponseMessages></SyncFolderItemsResponse></soap:Body></soap:Envelope>"}

01/27/2016 16:08:12.300    OUTLOOK (0x2f5)    0xb031d000    Outlook    ApxOL01    iboem    Monitorable    Assert Fired {"AssertMsg": "isRead"}

01/27/2016 16:08:12.301    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmpe    Verbose    {"Details": "Engine[Exchange folder Inbox]: There are 0 potentially modified local records since 1/27/2016 23:56:15 [218306876]"}

01/27/2016 16:08:12.326    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmpf    Verbose    {"Details": "Engine[Exchange folder Inbox]: There are 0 records marked for recovery."}

01/27/2016 16:08:12.326    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmpg    Verbose    Scanning map for required actions

01/27/2016 16:08:12.425    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmph    Verbose    {"Details": "Engine[Exchange folder Inbox]: There are 1 remote records to add locally"}

01/27/2016 16:08:12.425    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmpi    Verbose    {"Details": "Engine[Exchange folder Inbox]: There are 0 changes to push up"}

01/27/2016 16:08:12.425    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmpj    Verbose    {"Details": "Engine[Exchange folder Inbox]: There are 0 changes to pull down"}

01/27/2016 16:08:12.425    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmpk    Verbose    {"Details": "Engine[Exchange folder Inbox]: There are 0 conflicting records"}

01/27/2016 16:08:12.425    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmpl    Verbose    {"Details": "Engine[Exchange folder Inbox]: There are 0 local records to push up"}

01/27/2016 16:08:12.425    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmpm    Verbose    {"Details": "Engine[Exchange folder Inbox]: There are 0 local records to delete"}

01/27/2016 16:08:12.425    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmpn    Verbose    {"Details": "Engine[Exchange folder Inbox]: There are 0 remote records to delete"}

01/27/2016 16:08:12.425    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmps    Verbose    {"Details": "Engine[Exchange folder Inbox]: Reading remote record 21727"}

01/27/2016 16:08:12.431    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmp3    Verbose    {"Details": "Engine[Exchange folder Inbox]: Added local record id 92085"}

01/27/2016 16:08:12.431    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.exchange.ews    ibmwh    Verbose    {"Details": "FinishedSyncing() - setting the sync map's last sync date to: 1/28/2016 0:8:11 [218306888]"}

01/27/2016 16:08:12.467    OUTLOOK (0x2f5)    0xb031d000    Outlook    outlook.sync    ibmpq    Verbose    Sync Engine: Ending {"Engine": "Exchange folder Inbox", "Sync time": "1/27/2016 16:8:12 [218306408]"}