Email Issues

Revision as of 11:02, 15 July 2010 by Bryan Carson (talk | contribs)

See also

Problems connecting to Middlebury e-mail

  • Can you login to other Middlebury Services (like public computers, print stations, web directory (go/dir click logon link on bottom))?
  • Check basic things like IP and registration status.
  • If user is connected both to Eth wired network and to midd_unplugged, Outlook might be trying to connect through wireless network. To test this, disable wireless network & try again.

Create new Outlook or Entourage profile

For troubleshooting without risk of data loss, creating a new profile (Outlook) or identity (Entourage) is preferable to deleting accounts and setting up fresh. After new profile/identity has been in use and proven to contain all connections to accounts, and local or network address books, calendars, and personal (archive) folders, the old may be safely deleted. (good idea to delete extra identities in Entourage, as they take up space, and keep email cached on the local hard drive).

For details on how to create a new Outlook or Entourage profile see:

Webmail is not in Sync with Outlook, Entourage, Mac Mail, my Blackberry, etc.

Problem: My e-mail clients (Outlook, Entourage, Mac Mail, etc, etc) are not in sync with the e-mail server (represented by Webmail)

Solutions: Various. You don't want to use POP accounts. IMAP accounts are OK if you remember that IMAP by default only downloads your Inbox and your Sent items (though with some e-mail clients, IMAP sent items may still differ from the server's sent items). However if you're using the Exchange protocol (for the most part) and your mailbox does not sync properly, there are a few things to try: Make a new profile in Outlook (switch to a new identity in Entourage). Let it sync up. Does Outlook/Entourage match what you see in Webmail? If you want to avoid setting up a new profile, you can try repairing your current profile. For outlook, this involves running a Microsoft program called scanost.exe (http://support.microsoft.com/kb/287497), for Entourage this involves using the Entourage Database Utility (http://support.microsoft.com/kb/268322). In addition, for Outlook, you can also force Outlook to cleanup your profile: Exit out of Outlook (File => Exit), click on Start => Run => type in "outlook /cleanprofile" (without the quotes) and click OK. Finally, for Blackberries you should make sure that your are connected to our Middlebury blackberry server (not available for students), and not using POP or IMAP. For the blackberry, you may need to review your mail options - the blackberry by default shows you a "unified" view in your Inbox, dumping sent/received messages in the same "view" - it's possible to turn this off.

I've sent an email from a shared mailbox, but the email was not sent

Problem: You've sent email on behalf of a shared mailbox, but no one received the email

Cause: If you're using a new mailbox (recently created) you'll need to log into that mailbox directly before anyone can send on behalf of the mailbox.

Solution: Go to webmail and logon to the mailbox using the mailbox username/password. If you don't know the password for the mailbox contact the Helpdesk. NOTE: Student groups with questions about student group mailboxes should contact the CCAL office for password information.

Barracuda's Reputation Service

Occasionally users will be sent emails from outside, non-middlebury.edu addresses and not recieve them. Instead, the sender will recieve a bounceback email from Barracuda, describing how the sent email was blocked by Barracuda reputation.

Example Reputation Bounceback Email

Below is an example Barracuda Reputation bounceback email. The key line that allows us to tell the email was blocked by Barracuda's reputation service, rather than some reason is the one reading: 554 Service unavailable; Client host [feltwerks.com] blocked using Barracuda Reputation;
http: //bbl.barracudacentral.com/q.cgi?ip=xx.xx.xx.xx

Subject: FW: Mail delivery failed: returning message to sender

From: Mail Delivery System [mailto:Mailer-Daemon@xxxxx.com]
Sent: Wednesday, March 101, 2045 15:98 AM
To: xxxxxxxxxx@xxx.org
Subject: Mail delivery failed: returning message to sender

This message was created automatically by mail delivery software.

A message that you sent could not be delivered to one or more of its
recipients. This is a permanent error. The following address(es) failed:

SMTP error from remote mail server after end of data:
host reefshark.middlebury.edu [140.233.x.xx]:
554 Service unavailable; Client host [feltwerks.com] blocked using Barracuda Reputation;

Keep in mind there may be more text below what is listed above, usually specific to the content of the rejected email.

Helpdesk Response

The following is an example of the email you will likely get from the helpdesk when you report the issue:

The email sent to you was automatically rejected by our Barracuda spam filter. Barracuda uses a number of preset rules to
block certain emails automatically before they reach a user's inbox. In this case, Barracuda's reputation rule prevented
the email from arriving. Barracuda's reputation service will occasionally cause a certain email provider (e.g. myfairpoint)
to be blocked from sending email through Barracuda spam filters, usually because email addresses from that provider have
been responsible for sending out large numbers of spam emails.

Once a provider is blocked, every email sent from any user using that provider (ie any provider with an @myfairpoint.com
address) will be blocked as well. This process occurs at such a high level that there is no way for you or anyone here at
the helpdesk to allow the message or whitelist any particular user. The only recourse is for the email provider to contact
Barracuda directly and ask to be removed from the blacklist. You can find more information at the link included in the
bounceback email about Barracuda's reputation service and how providers can remove themselves from the blacklist:

If the user needs to send email to you urgently, they will need to either send to your middlebury.edu address from an
address with a different provider not blocked by Barracuda (yahoo, gmail, and windows live mail, or any other major
provider tend to be safe bets) or alternatively send to a non-middlebury address you can access.

If this is not a particularly urgent issue, you can always wait. Providers are frequently only blocked for a relatively
short period of time before becoming unblocked automatically, probably as the result of the statistical nature of
Barracuda's reputation service. Myfairpoint for example seems to be blocked every month or so for up to a week at a time,
before coming back off the reputation blacklist.

Message Content Rejected Error From Barracuda

Problem: Customer sent an e-mail with a URL and received an "Undeliverable" message from Barracuda. The body of the message from Barracuda states the following:

You do not have permission to send to this recipient.  For
assistance, contact your system administrator.
< #5.7.1 smtp; 550 5.7.1 Message content rejected, UBE,

Cause: In the hopes of preventing URL spam, the Barracuda spam filter blocks URLs to outside (non middlebury.edu) e-mail addresses. OR the email contains any kind of compressed file, including .zip, .rar, and .docx. 

Solution for URLs:

Solution for Attached Files:

  • Remove or rename the extension to something like .txt
  • In some cases whoever is recieving file will have to replace the original extension
  • OR don't save in compressed format (ie save as word 2003 document rather than 2007)

This is what the Helpdesk suggests when such an issue is reported (doesn't mention compressed files):

The most likely culprit for the Barracuda Spam Firewall to have rejected an outgoing message from you is an embedded link in your message.
You can send the text of links, but the text only.  In order to fool the firewall a link must look like this:
rather than
and the recipient would be required to copy and paste the address into their browser.

With yahoo or other free email accounts the weblinks show up at the bottom of the message and these are sometimes blocked.  Check your
message and see if it has these links and then resend with deleting the links before sending.  Let us know if you still have problems.

Alternatively, perhaps a more complete version (? feel free to edit):

Your emails were blocked by our spam filter (barracuda), which is why you received message undeliverable error messages. Without having copies of the
emails you were trying to send, I can only speculate, but usually outgoing emails are blocked for either having a compressed file with
extensions like .zip or .docx, or for having a link or multiple links the spam filter thinks are suspicious.

If you had an attached .zip or .docx or other compressed file, you can try sending the email again from an outside address (i.e. your
gmail address) so that the email never interacts with our spam filter. If your email contained any links, again you can try sending the
email again from an outside email address, or you can remove the http://www from the beginning of the link, or otherwise make the link
unclickable. If the link is unclickable or the http://www is missing from the beginning of the link, the spam filter should not block the
email. However, the person receiving your email will have to copy the link into his or her address bar and add the http://www again in
order to get to the website.

Unfortunately there is no way for us to change the spam filter's settings in order to allow individual outgoing emails. You can allow
individual incoming emails by going to go/spam, but there is no way to change the settings for outgoing emails.
Please let us know if you start having issues with outgoing emails that do not have attachments and do not contain links.

Common Errors for Rejected (bounced back) or Undeliverable E-mail

In these situations it is very important to look at and extract a few crucial lines from the bounce back message:

  1. The first line describes WHAT action failed (e.g. Delivery has failed to these recipients or distribution lists:)
  2. The second line describes WHO was the recipient (e.g. LS French School Community)
  3. The third line describes WHY the action failed (e.g. Your message wasn't delivered because of security policies )
  4. Under the line "Diagnostic information for administrators" are a few more tidbits of useful info
  • if you see "550 5.7.1 RESOLVER.RST.AuthRequired", then look lower down for "Received". Most distribution groups on campus require that messages TO those groups be sent via Exchange (Outlook/Entourage + an Exchange account, or Webmail) E.g. "Received: from outbound-mail-02.bluehost.com " means that this was sent from a foreign SMTP server. That is why sending this message failed.
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