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One of my managers have this problem of not receiving an email notification when a new entry is made in one of the sites on SharePoint, although he receives email from other groups and sites entries. Any idea on how can I fix this issue?

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Where do you create the alert? Do you create alert on a library or list?

Refer to the following article about users don't receive SharePoint Online alert notifications:

https://support.office.com/en-us/article/users-don-t-receive-sharepoint-online-alert-notifications-14fc22dd-e873-482c-844d-f67ad41313f1

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To receive the alert the person must be at least viewers of the site, check if this user is in the permission structure of the site/list/library

  • The person is one of the site viewers. – Fatma Q Mar 19 at 10:58
  • and does the list inherit permission from parent site? Is the alert set on IMMEDIATE or daily or weekly? – susan Mar 19 at 11:10
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Try this to troubleshoot the issue:

[Microsoft.SharePoint.Utilities.SPUtility]::SendEmail($web,0,0,$email,$subject,$body, $false)

And check "Immediate Alerts" timer job

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