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. -- YouTalk mailing list List address: [email protected] List information: http://entourage.mvps.org/support_options/list.html List moderator: [email protected], [email protected] To unsubscribe: mailto:[email protected]?subject=unsubscribe
