Bounce backs into Sharedmailbox

While sending emails to users from a sharedmailbox using sharedmailbox@domain.com  email to various users inside the organization, results into bounce back into sharedmailbox  similar to :

( Sharedmailbox is on Office365 )

From: System Administrator
Subject: Undeliverable.
Your message did not reach some or all of the intended recipients.
      Subject:      This is Subject Line
      Sent:      4/16/2018 9:05 AM
The following recipient(s) cannot be reached:
      UserA on 4/16/2018 9:05 AM
            This message could not be sent. Try sending the message again later, or contact your network administrator. You do not have the permission to send the message on behalf of the specified user. Error is [0x80070005-0x0004dc-0x000524].


I tried running following command to take a look if this userA have send on behalf rights to this mailbox and looks like he already does:

  Get-Mailbox -Identity SharedMailbox | FL GrantSendOnBehalfTo

  UserA, UserB, User C ...

Many bounce backs are going into Sharedmailbox directly.

Can anyone point me to where this issue could be ?

thanks
Nick PerksIT DirectorAsked:
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zvitamConsultantCommented:
Hi,

1. This issue is a known issue with off-line address books. re-download the global address book may resolve the issue.
2. If the User has "Hide from address lists" ticked you may also have this issue when trying to send him a message from a shared mailbox.
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systechadminConsultantCommented:
this is because of the OAB is not udpating, its known issue. you will need to close the outlook and then go to the Path of OAB  file location. Delete OAB file and then start outlook.

C:\Users\Username\AppData\Local\Microsoft\Outlook\Offline Address Books
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Vasil Michev (MVP)Commented:
How do you have the Shared mailbox added in Outlook? Depending on how it's added, Outlook will either use Send As or Send on behalf of permissions, which might be the issue here.
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Nick PerksIT DirectorAuthor Commented:
It shouldnt have to do with GAL because all users sending emails from this mailbox are getting this error. Checked by sending email from OWA as well as Outlook.

After making sure that user have both Send as rights and send on behalf to rights to this sharedmailbox, its still bouncing back. I checked OWA office 365 and local Outlook:

_____________________________________________
From: System Administrator
Sent: Tuesday, April 17, 2018 8:45 AM
Subject: Undeliverable: Testing


Your message did not reach some or all of the intended recipients.

      Subject:      Testing
      Sent:      4/17/2018 8:45 AM

The following recipient(s) cannot be reached:

      Ronald Fagan on 4/17/2018 8:45 AM
            This message could not be sent. You do not have the permission to send the message on behalf of the specified user.

__________________________________________________

Diagnostic information for administrators:
__________________________________________________

Error is [0x80070005-0x000004dc-0x00000524].

Exchange response headers:
      request-id: 49229735-b3ad-4065-a770-4fef614bf72a
      X-ServerApplication: Exchange/15.20.0696.003
      X-FEServer: DM5PR21CA0033
      X-BEServer: YQBPR0101MB2033
      X-CalculatedBETarget: YQBPR0101MB2033.CANPRD01.PROD.OUTLOOK.COM
      X-RequestId: {FB0EE549-85A2-4AEE-A4E8-0041E23EB226}:439
      X-ClientInfo: {8023AD2D-8572-4A54-B6E4-B2D437269272}:21320021
      X-ElapsedTime: 28
      X-BackEndHttpStatus: 200
      X-ResponseCode: 0
      X-DiagInfo: YQBPR0101MB2033
      X-RequestType: Execute
__________________________________________________

ROPs Summary:

      0: ropSetProps (10) Processed(1) Completed(0)
            ROP result: 0
            Response codes: 0
      1: ropSetProps (10) Processed(1) Completed(0)
            ROP result: 0
            Response codes: 0
      2: ropFlushRecipients (14) Processed(1) Completed(0)
            ROP result: 0
            Response codes: 0
      3: ropSetProps (10) Processed(1) Completed(0)
            ROP result: 0
            Response codes: 0
      4: ropTransportSend (74) Processed(1) Completed(0)
            ROP result: 0
            Response codes: 1244
__________________________________________________

Response Exceptions:

ROP Index: 4
ROP Associated: ropTransportSend (74)
Microsoft.Exchange.Data.Storage.SendAsDeniedException: Can't transport send message. ---> Microsoft.Mapi.MapiExceptionSendAsDenied: MapiExceptionSendAsDenied: Unable to transport send message. (hr=0x80070005, ec=1244)
Diagnostic context:
    ......
    Lid: 52176   ClientVersion: 15.20.696.3
    Lid: 50032   ServerVersion: 15.20.696.6008
    Lid: 35180  
    Lid: 23226   --- ROP Parse Start ---
    Lid: 27962   ROP: ropDeletePropsNoReplicate [122]
    Lid: 27962   ROP: ropSetProps [10]
    Lid: 27962   ROP: ropFlushRecipients [14]
    Lid: 31418   --- ROP Parse Done ---
    Lid: 55847   EMSMDBPOOL.EcPoolSessionDoRpc called [length=134]
    Lid: 43559   EMSMDBPOOL.EcPoolSessionDoRpc returned [ec=0x0][length=408][latency=1]
    Lid: 52176   ClientVersion: 15.20.696.3
    Lid: 50032   ServerVersion: 15.20.696.6008
    Lid: 35180  
    Lid: 23226   --- ROP Parse Start ---
    Lid: 27962   ROP: ropSetProps [10]
    Lid: 27962   ROP: ropTransportSend [74]
    Lid: 17082   ROP Error: 0x4DC    
    Lid: 44949  
    Lid: 21921   StoreEc: 0x4DC    
    Lid: 27962   ROP: ropExtendedError [250]
    Lid: 1494    ---- Remote Context Beg ----
    Lid: 41788  
    Lid: 44092  
    Lid: 41232  
    Lid: 60208  
    Lid: 37136  
    Lid: 34608  
    Lid: 55056  
    Lid: 42768  
    Lid: 56112  
    Lid: 52807  
    Lid: 33016   StoreEc: 0x4DC    
    Lid: 40748   qdwParam: 0xD88E3A0000000001
    Lid: 57132   qdwParam: 0x0              
    Lid: 63016   dwParam: 0x4A
    Lid: 39640   StoreEc: 0x4DC    
    Lid: 45434   Guid: 8532dd53-1e1f-4a91-aa33-26f63d9f4e7e
    Lid: 10786   dwParam: 0x0        Msg: 15.20.0696.003:YQBPR0101MB2033:34fe08d6-7f88-4e23-80e8-21d18c3f3e2e
    Lid: 1750    ---- Remote Context End ----
    Lid: 31418   --- ROP Parse Done ---
    Lid: 22753  
    Lid: 21817   ROP Failure: 0x4DC    
    Lid: 59285  
    Lid: 46997   StoreEc: 0x4DC    
   at Microsoft.Mapi.MapiExceptionHelper.InternalThrowIfErrorOrWarning(String message, Int32 hresult, Boolean allowWarnings, Int32 ec, DiagnosticContext diagCtx, Exception innerException)
   at Microsoft.Mapi.MapiExceptionHelper.ThrowIfError(String message, Int32 hresult, IExInterface iUnknown, Exception innerException)
   at Microsoft.Mapi.MapiMessage.TransportSendMessage(PropValue[]& propsToReturn)
   at Microsoft.Exchange.Data.Storage.MapiAccessor.TransportSendMessage(Object mapiObject, ExTimeZone timezone, PropertyDefinition[]& propertyDefinitions, Object[]& propertyValues)
   --- End of inner exception stack trace ---
   at Microsoft.Exchange.Data.Storage.MapiAccessor.TransportSendMessage(Object mapiObject, ExTimeZone timezone, PropertyDefinition[]& propertyDefinitions, Object[]& propertyValues)
   at Microsoft.Exchange.Data.Storage.ItemSender.TransportSend(ICoreItem coreItem, PropertyDefinition[]& propertyDefinitions, Object[]& propertyValues, IEventDispatcher eventDispatcher, IMapiAccessor mapiAccessor)
   at Microsoft.Exchange.Data.Storage.CoreItem.TransportSend(PropertyDefinition[]& properties, Object[]& values)
   at Microsoft.Exchange.RpcClientAccess.Handler.Message.TransportSend()
   at Microsoft.Exchange.RpcClientAccess.Handler.RopHandler.<>c__DisplayClass153_0.<TransportSend>b__0()
   at Microsoft.Exchange.RpcClientAccess.Handler.ExceptionTranslator.TryExecuteCatchAndTranslateExceptions[TResult](Func`1 protectedCode, Func`2 errorCodeExtractor, Boolean noThrow, TResult& result, Exception& exception, ErrorCode& errorCode)


Transport-Send failed: failure enum(25), HResult(0x00000000), EC(1244).
Transport-Send failed: failure enum(22), HResult(0x00000000), EC(1244).
Submit-Message failed: message id(2), failure enum(13), HResult(0x80070005), EC(1244).
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Nick PerksIT DirectorAuthor Commented:
I am sorry, so Outlook OWA for sharedmailbox works !! But sending emails throug local Outlook Fails!
I tried downloading address book by going to file - account settings and download address book. closed and reopened outlook but this message bounce back comes back right away.
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Nick PerksIT DirectorAuthor Commented:
further testing reveals that when they add the mailbox as non-cached in their outlook, email goes through ( but mailbox gets very slow )
Cached exchange mode reveals that error right away.

Anyway to get Cached exchange mode in Outlook work ?

Thanks
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Vasil Michev (MVP)Commented:
Dont use any stored autocomplete entries, make sure you select the address directly from the GAL. Also make sure you are using the right method, as I mentioned above there is difference in behavior depending on how the mailbox is added in Outlook. Read here for more details: https://www.michev.info/Blog/Post/1430/send-as-send-on-behalf-of-and-permutations
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Nick PerksIT DirectorAuthor Commented:
ok thanks. Thats make me understand clearly.

I am now running into a seprate issue, trying to assign sendonbehlafof permission for this shared mailbox.
I want 5 users who currently have full access to this mailbox to also have sendonbehalfof rights.

I tried running the following command sucessfully:

Set-mailbox sharedmailbox -Grantsendonbehalfto @{add="1","2",3","4"}  

The issue is that the permissions after about 15 minutes reverts back to ONLY user 1 and 2,3,4 users are automatically removed from sendonbehalf permissions. I want this permission to stay on all 4 users.

Any clue as to why this may be happening and how to resolve ?
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Vasil Michev (MVP)Commented:
Not sure about this one, perhaps a replication issue? Or something is overwritting the changes? Consider opening a new question for that...
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Nick PerksIT DirectorAuthor Commented:
FYI I had to call MS and their exchnage online tech said they had to fix something on their end to ensure the sync is working correctly, and once he did that the permission on all 4 users stayed.

Regarding my original question in this post, the answer was related to my issue of the permission not staying As well as Address book download. I am going to assign points as per your help.

thanks very much for all your inputs!
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