Thanks for sharing!! I'll get this added to the Entourage Help Page. Between
the update and 5 clients having database disasters at once I'm swamped right
now.

-- 
Diane 


On 7/21/09 8:43 AM, "John Reed" <[email protected]> wrote:

> There are have been a large number of posts across the Internet describing
> problems with sending mail using Entourage after installing an OS X server
> or with a new installation of Postfix.  Many of these queries report
> problems but no solutions.  The also can crop up when a user tries to use
> Entourage with a mail system the first time.  I installed an OS X server and
> immediately encountered this with my Entourage clients.
> 
> A typical message on the Entourage client is as follows:
> 
> Cannot send mail.  The SMTP server does not recognize any of the
> authentication methods supported by Entourage.  Try changing the SMTP
> authentication options in Account settings or contract your network
> administrator.
> 
> OS X uses postfix as its mail server.  When you install it, it sets the SMTP
> port to 25.  Your administrator may have changed that to 465 or 587 and you
> should check to see if that is your problem.  If so, you need to go to
> advanced settings and override the port settings.  You can run a couple of
> quick experiments, for example, by entering 587.  However, most of the
> problems I have read about on the web seem to be with new installations of
> OS X Server where the port has not been changed.
> 
> The important point is that when the OS X mail server is installed, the SMPT
> server is set to port 25 and neither of the other two ports are available.
> If override is checked in advanced SMTP settings and there is anything other
> than 25 in the box, Entourage may be set to the wrong port for the server
> settings.
> 
> It also turns out that Entourage, the client software, can play naughty in
> this situation.  If on the OS X server (an presumably postfix as well) you
> set "plain talk" as the encryption method for authentication and then
> require a user id and password, Entourage will not recognize "plain talk."
> The encryption method has to be at least the "login" level on the mail
> server to be recognized.  There are stronger encryption methods but we have
> not tried those. They may work as well.
> 
> So in the end, the settings for SMTP in Entourage have to be as follows
> assuming you are using port 25 and not overriding the port settings and you
> are using "login" and not one of the more advanced forms of encryption on
> the server:
> 
> Enter the name of your mail server.
> 
> Choose advanced settings:
> 
> Do not choose secure socket layer
> 
> Uncheck the override the default port setting if it is checked
> 
> Check require authorization
> 
> Uncheck or do not check the box for require the same settings as for
> receiving.
> 
> Check the box for user and password
> 
> For user id, enter the short name for the user name that was entered in the
> OS X Server (or postfix) for accounts
> 
> For password use the password for the account
> 
> Assuming that everything is set properly this will probably work.
> 
> For those who may be experiencing this problem because they have newly
> installed Entourage, you need to find out two things from the administrator.
> The first is the port number and the second in the encryption setting level
> of the server.  If the administrator is using "plain talk" and requiring a
> login I think you are out of luck.  If the administrator is using a more
> advanced form of encryption on the server, for example, "Login" then it is
> just a matter of getting the port right.  It is not clear what happens if
> with more stringent forms of encryption such as Kerebos.
> 
> Hope this helps others.  It took a few hours and lots of experimeting with
> OS X, the Apple mail and Entourage clients to figure all this out.
> 
> 
> 
> 
> 
> 
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