Tech Line
Sending from Entourage? Think Again!
What to do if your Entourage email client allows you to receive email, but not send any.
Chris: How do you set Send permissions in Exchange 2003
Server to allow a mailbox user to send mail? There seems to be a discrepancy
between the version we have and our instructions.
Apparently this is what should work: Users/[right click]Properties/Security/Send
As/ then check Allow or Deny. When we right click there is no security
option. On the server side there is an issue with Send Only. Entourage
receives the 5550 error, which is essentially the server denying access
to send from that account.
The guy who usually does this is gone, the developer is trying ... that's
not going so well. I've research Microsoft's Web site; also not helpful.
Any info you could pass along would be greatly appreciated.
— Audrey
Answer: Audrey and I worked out most of the details of
her problem over the telephone. The problem of not seeing the Security
tab for a user account object in Active Directory is something that nearly
all of us have experienced.
A few years ago, I had a similar experience with the Active Directory
Users and Computers MMC. I was following a set of procedures to solve
a problem, and low and behold — there was no Security tab! After
some digging around, I was able to see that to see many of the "Advanced"
configuration options in Active Directory Users and Computers are visible
once you click the View menu and select Advanced Features. For you Saturday
Night Live fans, somewhere in the world Nick Burns is asking "Was
that so hard?"
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When new mailbox objects are created, the Self group is automatically
assigned Read and Full Mailbox Access permissions to the mailbox object.
So by default, users should have the appropriate permissions to send their
own e-mail. After viewing the permissions for her user mailboxes, Audrey
was able to see that they indeed had the proper permissions. However,
user's still could not send e-mail from their Entourage client software.
With appropriate permissions on the server and with users on other systems
having no trouble, we were led to look at the Entourage client settings
on the newly deployed workstations. As it turned out, the clients were
not configured to authenticate with their SMTP (Exchange) server. To solve
this, she had to perform the following steps in Entourage:
- Click the Tools menu and select Accounts.
- In the Accounts dialog box, click the Exchange tab.
- Double-click on the user's Exchange email account and in the email
account dialog box select the Advanced Sending Options button.
- Check the SMTP Server Requires Authentication checkbox.
User's had been able to receive e-mail, but could not send. This was
because when sending e-mail, they were not authenticating with the Exchange
Server, which was configured to require authentication. For more information
on securing SMTP authentication on Exchange 2003, take a look at Microsoft
Knowledge Base article 823019,
"How to Help Secure SMTP Client Message Delivery in Exchange 2003."
The article not only takes you through the process of securing the SMTP
virtual server, but also points out the changes to e-mail clients that
the SMTP security changes require.
This e-mail client problem is typical of many of the client-server troubleshooting
issues that we run into. First, it's important to isolate the source of
the problem: client or server. With several new workstations deployed,
and other users having no problems sending mail through the server, all
symptoms pointed to a client configuration problem. In this case, client
misconfiguration was the ultimate cause, much to Audrey's relief.
[Chris Wolf has just released Virtualization:
From the Desktop to the Enterprise (Apress) and welcomes your virtualization
questions for this column. —Editors]