Alert to group not working on Sharepoint 2010!

Question

Hello,
We have a SharePoint 2010 Server which on the front page we have a news list. We have migrated to 365 and since then the alerts are not working properly. We have a local SMTP server that we use to rely to 365 since SharePoint does not support TLS by itself.
The SMTP server is working because we can set up alerts on individuals and the emails are coming. The issue is with the group. I have tried several groups but still the same issue. On some groups we receive the initial email about the creation of the alert,
but no mails after that. I have checked also the Immediate Alert service and is successful. I have checked in the  mail flow on 365 and I can see the initial creation of the alert mail sent to all in the group, but the alerts on changing anything on the
list does not come into 365, so it must be a SharePoint issue which I can`t determine since the immediate alert service is running...
Can you please provide a feasible solution for this issue?
Thank you very much.
DOVC
Best Regards, Valentin Doru System Administrator

Answer 1

Hi Valentin,
please also open a thread at o365 community, because seems this issue happened at o365.
to try, perhaps you can re-add the group also, because it may refresh the properties from the AD group to o365.
and you may check these workaround for testing:
Option 1: Use a Redirection User
created a user in Office 365. This user is licensed to use SharePoint Online and Exchange Online.
In Exchange Online, create Distribution Groups, which are standard Distribution Group that allows however in Delivery Management also Senders outside of organization, as the SharePoint Sender is not part of the Exchange Org.
In Exchange Online for the User Exchange Forwarder, created Inbox Rules. The rule is checking the Subject for a keyword and as action redirect the E-Mail to the DG and deletes it right away.
repeat this for other DGs as well.
In SharePoint Online grant the user Exchange Forwarder access to the Site to access the List
Now there are two important steps:
1)      The Alert Title needs to include the token we look for in the Exchange rule
2)      The “Send Alerts To” needs to be our “Exchange Forwarder”
When everything is set up an Alert will be received by Exchange Forwarder and then forwarded to the DG.
Option 2: Use a custom Workflow with the Send E-Mail To Activity
In Exchange Online creat a Distribution Groups, which are standard Distribution Group that allows however in Delivery Management also Senders outside of my organization, as the SharePoint Sender is not part of the Exchange Org.
Using SharePoint Designer create a custom Workflow like the one below. In the Send E-Mail activity I specified the external SMTP Address of the DG as To-Address.
When the Workflow is executed an E-Mail is sent directly to the DG:
Background:
When sending an Alert, SharePoint is doing a Security Trimming. So SharePoint wants to be sure the recipient of the Alert has permissions to see the List Content the Alert is about. Therefore we cannot enter an SMTP-Address for an Alert but need to specify
a Security Principal known to SharePoint.
In a Workflow we don’t need to do this kind of Security Trimming. The creator / designer of the Workflow need to take care whom to send what information.
Side note: Alerts and Workflow Send E-Mail To Activities are the only possibilities in SharePoint Online to send E-Mails. Custom solutions (Sandboxed Solutions) will not work.
Regards,
Aries
Microsoft Online Community Support
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