When Groove Administrator email doesn't reach the user

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 Here's a scenario for anyone who administers a Groove domain from Groove Enterprise Services or Groove Hosted Services (i.e., from a Microsoft-hosted server). Let's say that one of your users lost their account and needs their account backup. No problem -- the server has a current one. You use the Services Manager UI to email the account backup file to the user, and you don't get an error or bounce message, but the user never receives the email. What could be wrong?

Most likely, the message has been filtered out by an email server between the Groove server and the recipient. Here's the problem: email from the hosted Manager has four required fields: Sent To, From, Subject, and Message. "From" is intended for you to enter your administrative address so that you can receive bounce messages and replies. However, many modern email systems silently discard messages in which the "From" address does not match the source in the first "Received" header, because fake from addresses are frequently used in spam and in malicious messages.

There are two ways to work around this:

  • (Preferred) Use the Manager option to download the backup, rather than emailing it. You can either move it to a network location that the user can access and provide the user with a pointer to it, or you can move it to a network location that you can access, and then email it from your own account.
  • Have the administrator of the mail server white-list the host that will send the email. Inconveniently, I cannot provide host names, because the sending systems occasionally change without notice, as part of load-balancing on the Microsoft servers. To find the sending host for your case, send mail from the Manager to yourself at a known open destination (for example, if your corporate email performs this check, create a hotmail account and send mail to yourself there), and then check the headers to see where the message originated.

When reading headers, the earliest "Received" is last in the list. For example, if the mail message originates at Host1 and goes through Host2, Host3, and Host4 to reach your SMTP server at Host 5, the "Received" portion of the header will look something like this:

Received: from  Host4 <ip address> by Host5 <ip address> with <SMTP Server and id>; <day>, <date> <time>

Received: from  Host3 <ip address> by Host4 <ip address> with <SMTP Server and id>; <day>, <date> <time>

Received: from  Host2 <ip address> by Host3 <ip address> with <SMTP Server and id>; <day>, <date> <time>

Received: from  Host1 <ip address> by Host2 <ip address> with <SMTP Server and id>; <day>, <date> <time>

In this case, you would want the mail administrator to whitelist Host1, so that all mail from Host1 is allowed.