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Indie101

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Mail not being delivered to Distribution group in Hybrid 365 On Premise (Exchange 2010)

New distribution group for a customer not working, they have hybrid on premises setup (Exchange 2010)

With distribution security group in Exchange On Premises,

I realise there are two groups

  Mail-enabled universal distribution groups (also called distribution groups) can be used only to distribute messages.

   Mail-enabled universal security groups (also called security groups) can be used to distribute messages as well as to grant access permissions to resources in Active Directory.

This is a universal security group, there is a group in Office365 setup, users are complaining that no one is receiving mail through the distribution group

Is there a checklist I can use to go through this? Just want to check the validity, someone else would have set this up, I've been added to support for our Office365 group and want to learn fast and troubleshoot this and see the best way to do this

Thanks in advance :)
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Indie101

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Avatar of Sajid Shaik M
check the distribution group members first...  all the best
first check if the Distribution Group created in On-premises is synced with O365.

Then check if the O365 users are able to view that DG in there Outlook.

Also confirm only O365 users from the group are not able to receive the mails ??

Let me know the result so that we can identify the root cause and solve the issue
Try to remove then recreate DL - then add users
Thanks guys, in Office365 it was created as a security group, and not a distribution group,

There are only 4 users in it, all external users

There is also a user mailbox with same name and an AD security group (which i changed to distribution) and did an AD connect delta sync successfully (I suspect whoever made it made a mess of it)

Can someone send me the steps 1-2-3 for new distribution group in Hybrid O365

Is it as per this?

https://support.office.com/en-us/article/create-distribution-lists-in-the-office-365-admin-center-b1ffe755-59e5-4369-826d-825f145a8400
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Avatar of Neha Agarwal
Neha Agarwal
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Found the issue, whoever created it made a remote user mailbox instead of a distribution group

I want to create a distribution group with the same email address,

So as far as I know I need to delete this and do a purge with powershell (anyone have the command handy) and recreate new distribution list in Exchange Console)

Anything else I would need to do?
Remove-Mailbox -Identity "mailbox alias" -Permanent $true
Thanks Neha that purges the user mailbox so I can use the address with distribution list? Can you explain what it does, thanks in advance :) ( I mean whats the technical term for that PS command, soft delete\purge etc)
Thanks Neha do i run Remove-Mailbox -Identity "mailbox alias" -Permanent $true  from Exchange Console Shell on Exchange 2010 Server?
yes, the above command will purge the mailbox of which you want to use the mail address.
After purging on on-premises,you have to wait for the sync to occur in O365. Once the ID is not visible in O365 portal .,you can create the DG with same address

Command is for purging the mailbox. With Soft delete you can restore the mailbox,but with the above command, mailbox will delete permanently
Is the mailbox resides in on-premises, or its moved to O365??
Mailbox is on premise Exchange Console as a remote user mailbox and is unlicensed in O365
Thanks Neha, gave you full points, getting an error with

Remove-Mailbox -Identity "mailbox alias" -Permanent $true when i put in name in mailbox in alias, tried PS and Exchange Mmgt shell
run the below command in Exchange powershell and in exchange powershell online and share the output.

get-mailbox -identity alias | fl


When we say remote mailbox it means the mailbox is moved to O365.So first we need to validate where the mailbox resides.
I ran it on Exchange Mmgt shell and got The operation couldn't be performed because object 'alias' couldn't be found on

Ran it on Exchange Powershell and got

The term 'get-mailbox' is not recognized as the name of a cmdlet, function, script file, or operable program. Check the
 spelling of the name, or if a path was included, verify that the path is correct and try again.
Connect with Exchange online powershell check there with get-mailbox

I believe mailbox is in O365 which is the reason its not showing in the EMS of on-premise
Thanks Neha I can see the mailbox in Exchange Online

Just say name of mailbox is Test

Do i just run Remove-Mailbox -Identity "test" -Permanent $true from Exchange Online
Is the command not remove-mailbox -Identity "test" -PermanentlyDelete $True
yes, and then you have to delete the ad account from your on-premise.
After that wait for the sync.
Run the below command

Remove-Mailbox -Identity "test" -PermanentlyDelete
Thanks Neha, get below message whomever set it up made a dogs dinner of it :)

This mailbox cannot be permanently deleted since there is a user associated with this mailbox in Azure Active Directory. You will first need to delete the user in Azure Active Directory. Please refer to documentation for more details.

So do i just do the following to make it work

1.Delete the user in Azure AD
2.Purge mailbox with remove-mailbox -Identity "test" -PermanentlyDelete in Exchange Online
3.Delete AD account from On Premise
4.Delta Sync
5.Create new distribution group On premise , then Sync again



Thats it (will document this going forward, thanks very much for your help with this) Excellent stuff!!
Thanks Neha, I have deleted in AD and will sync to see if changes carried over to AAD (how long does this take?)

Once this is completed

1.I will purge mailbox with remove-mailbox -Identity "test" -PermanentlyDelete in Exchange Online

2.Then delta sync again and create new distribution group On Premise then Sync again

Is that it? Thanks again :)
it takes 30 mins by default. or else you can force the delta sync from AADConnect server

read this blog which will clear all your doubts
https://www.brisk-it.net/deleting-office-365-mailbox-hybrid-deployment/
Thanks Neha, I had to purge the user mailbox, so besides connecting to Exchange Online, had to connect to MSOnline as well

get-msoluser -ReturnDeletedUsers -UserPrincipalName test@test.com | Remove-MsolUser -RemoveFromRecycleBin

I will now delta sync and create the distribution list in on premise AD and sync again

Thanks :)