No SMTP Authentication for Thunderbird or Outlook?
Wow, this one is killing me. I have a Mini with Snow Leopard Server running mail. I use CRAM-MD5 authentication and SSL connections for both IMAP and SMTP.
I HAD to get a Windows 7 netbook to run QuickBooks and Office (not my choice), so now I'm trying to connect either the Outlook 2010 client or a Thunderbird client with one of my accounts so QuickBooks can send invoices, etc...
I was able to connect to IMAP with both clients using the SSL connection. I can't remember the level of authentication that worked for Thunderbird, but I had to drop to PLAIN for Outlook to work.
Now the hair-pulling problem... The SMTP authentication and connection methods don't work for either client. NONE of them in any combination. Even dropping SSL and going to PLAIN don't work.
Does anyone have any idea what this is all about?
Thanks.
MacBook Pro,
Mac OS X (10.6.4),
MacMini Server - latest Snow Leopard
Are you even able to connect to the mail server via telnet?
If you're getting to the mail server, can you connect to port 25? (eg: using telnet to connect to port 25)
If you can connect into port 25 via telnet, is it responding like a mail server?
If you've connected to port 25 and it's a mail server, what (other) ports are you connecting to?
Are you using authenticated connections for sending? Port 587, etc.
If you're connecting, what sort of relevant "stuff" might be present in the mail server logs after a failure?
Can you connect from that Windows 7 box and clients to another IMAP or POP3 server elsewhere?
I'd also encourage you to pursue this with the Microsoft Windows and Microsoft office forums and folks; Windows is the most central part of this, and you're here connecting to a standard IMAP or POP3 server. Which means this is primarily with the client platform, and secondarily with the server. You could, for instance, be connecting that Windows box to most any platform.
+No error messages - just no connection. Just says not able to connect. With Thunderbird, it the error log on the client says the server doesn't support TLS. The server's SMTP log says "fatal, too many errors, program terminated"+
How is the local network configured?
+Can you be more specific?+
Are you even able to connect to the mail server via telnet?
+I don't use telnet - don't even know what it is.+
If you're getting to the mail server, can you connect to port 25? (eg: using telnet to connect to port 25)
+Yes, I can connect to port 25 with the clients if I drop to PLAIN. I know this because the Outlook client says it's connected but the authentication won't occur - it just keeps asking for the password over and over. I think is particularly odd in the case where I've dropped to PLAIN+
If you can connect into port 25 via telnet, is it responding like a mail server?
+No responses+
If you've connected to port 25 and it's a mail server, what (other) ports are you connecting to?
+Not sure what you're asking. With another service?+
Are you using authenticated connections for sending? Port 587, etc.
+As I already indicated, those don't work.+
If you're connecting, what sort of relevant "stuff" might be present in the mail server logs after a failure?
+See the log messages I mentioned above.+
Can you connect from that Windows 7 box and clients to another IMAP or POP3 server elsewhere?
+Don't know - don't have one.+
I'd also encourage you to pursue this with the Microsoft Windows and Microsoft office forums and folks; Windows is the most central part of this, and you're here connecting to a standard IMAP or POP3 server. Which means this is primarily with the client platform, and secondarily with the server. You could, for instance, be connecting that Windows box to most any platform.
+I'll certainly follow up with their forums. This seems, however, like it might be a pretty common problem and it's certainly relevant for this forum. Maybe someone else on the forum could help? Thanks.+
Paul, I'm getting a similar message from Outlook 2010 on my new iMac saying cannot connect with outgoing server. Server requires authentication. Is this in anyway similar to your issue? I can receive email from my Verizon ISP mail server using Outlook but cannot send. Have searched Microsoft Outlook Q&A, and found suggestion to try different ports, but those efforts failed as well.
I do have a similar problem, and it is a helo command rejected. The exact message is:
The message was not sent, one of the destinations was rejected by the server. Your e-mail address is "alvaro@ledific.com". Subject 'test', Account: 'mail.incontrol.com.ec', Server: 'mail.incontrol.com.ec', Protocol: SMTP, Server answer: '504 5.5.2 <ALVARO>: Helo command rejected: need fully-qualified hostname', Port: 25, Security (SSL): No, Server error: 504, Error number: 0x800CCC79.
All my Macs work fine, but PCs with Windows (XP,7,Vista) receive mails but can´t send e-mails.
If this is something I have to change on main.cf, where can I find this file?
I am using a Mac Mini as a server with the latest Snow Leopard version
I'm having continued problems with this issue and none of the solutions listed helps me out. Some Windows/Outlook clients can connect and some can't. Al have different combos of Windows and Outlook versions and their doesn't seem to be a common thread.
Windows 7 Outlook 2003 - no go
Windows 7 Outlook 2007 - 2 good, one no go
Windows 7 Outlok 2010 - fine
Windows Vista Outlok 2007 - fine
??????
Basically, it's making the server work in a non-standard way so that something that's broken can work. Not the best approach when trying to keep a secure server.
Is a real fix even available? Seems to me the latest version of Outlook (that's actually been around for a while) connecting to Snow Leopard Server is not exactly an unexpected circumstance.