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Jonesy · Dec 11, 2006, 03:10 PM

I have a work mail account which checks e-mails with SSL fine but can't send them at all. I have asked the IT people to see if they can help me get it working. They are only geared up for Outlook and don't have much clue about Macs. Has anyone had similar problems?

JKT · Dec 11, 2006, 04:08 PM

Can it send any e-mails, regardless of whether they are SSL or not? If not, it is possibly a port problem (e.g. many ISPs block Server port 25 which prevents you from sending e-mails, in preference for another alternative such as 587).

Jonesy · Dec 11, 2006, 04:14 PM

All of my other e-mail accounts are fine. All of the settings are correct as far as my work e-mail provider is concerned. This is only a problem for this particular account.

Is Mail known to have a problem with SSL mail specifically? Should I be able to find the problem in an console logs?

Mithras · Dec 12, 2006, 07:27 AM

Does it report any error when you attempt to send? e.g. a certificate error?

Jonesy · Dec 12, 2006, 09:22 AM

Activity viewer says "Connecting to server smtp1.xxx.xxx" for ages then the only error I get is "Cannot send message using the server smtp1.xxx.xxx. Use the pop-up menu below to try a different outgoing mail server. All messages will use this server until you quit Mail or change your network settings" which is not very helpful in working out exactly where the problem is. I suspected a certificate but the IT helpdesk did not think I should need anything special (although they are geared up for Windows only).

Mithras · Dec 12, 2006, 10:18 AM

As JKT noted, go to accounts, click on the account, then at the bottom (in the "Outgoing Mail Server" section) click the "Server Settings..." button. What do the settings show, in particular for SSL and port?

Jonesy · Dec 13, 2006, 04:58 PM

I am grateful for the help everyone has offered but I have already configured my smtp server according to the suggested settings. The port number etc. are correct. I don't think I should mention the settings on a forum as the server is supposed to be secure and even getting access to the description of how to set it up requires password protected access.

My main reason for posting was to ask if there was somewhere my failed attempts to send mail would be logged with any useful errors. The logs in Console don't seem to show anything. I also noticed that Mac OS X uses OpenSSL and I wondered whether any known incompatibilities there could be the cause of my trouble.

jrafter · Dec 13, 2006, 05:50 PM

Mail.app is known to have compatability problems with some certificates. You might try Thunderbird just to see if it works. If the problem is with Mail, and unless the server can be configured appropriately, there's probably little you can do.

legacyb4 · Dec 13, 2006, 06:51 PM

What kind of server are you trying to relay through?

Jonesy · Dec 17, 2006, 03:40 AM

Originally Posted by legacyb4

What kind of server are you trying to relay through?

I'm not sure. The mail server belongs to the UK National Health Service. The government has sold its soul to Microsoft so I believe it is theirs.

Jonesy · Dec 17, 2006, 03:41 AM

Originally Posted by jrafter

Mail.app is known to have compatability problems with some certificates. You might try Thunderbird just to see if it works. If the problem is with Mail, and unless the server can be configured appropriately, there's probably little you can do.

Thanks for the suggestion. I will try Thunderbird.

Jonesy · Dec 24, 2006, 07:49 AM

Thunderbird does work. This must be a problem with Mail then. If this is due to a problem with a certificate then is there a way to find out which one and replace it in Keychain? Is it not as simple as that?

I had hoped that in the last minor update the change to OpenSSL would help but it hasn't. I have reported this to Apple. Hope 10.5 holds the fix.

Thanks for your help everyone.