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Mac Forum / Applications / Mac Applications / December 2006Mail refuses to send emails
Hi, I have trouble setting up Mail to send any kind of email. My company has 2 servers. Server 1 uses IMAP/SSL + SMTP + SSL with authentication, Server 2 is an exchange server and uses plain SMTP with authentication. I can read emails from both of them but get all kinds of error messages when I try to send emails. E.g. "Cannot send message using the server (null)" "SMTP server XXXX doesn't support authentication." To see if this was a network or firewall problem I installed Thunderbird and Opera. I can use both SMTP servers from both Thunderbird and Opera Mail without a problem on the same machine. I also checked the Console but there were no error messages there. What next? -- nyenyec > Hi, > [quoted text clipped - 21 lines] > > -- nyenyec Go to Mail / Preferences / Accounts / Outgoing Mail Server (SMTP) / Server Settings / Authentication / select the option that fits your service. > Go to Mail / Preferences / Accounts / Outgoing Mail Server (SMTP) / > Server Settings / Authentication / select the option that fits your > service. That's the problem. I do have the correct server settings. The error messages I get are completely bogus. -- nyenyec > > Go to Mail / Preferences / Accounts / Outgoing Mail Server (SMTP) / > > Server Settings / Authentication / select the option that fits your [quoted text clipped - 4 lines] > > -- nyenyec The error message is not bogus it's telling you that somewhere in your setup you have entered the wrong information. Did you in the Authentication option select "None" if it is true your ISP does not need authentication. I would be surprised that an ISP would not have some form of authentication when sending email. > Did you in the Authentication option select "None" if it is true your > ISP does not need authentication. > > I would be surprised that an ISP would not have some form of > authentication when sending email. Some SMTP do not use authentication. Definitely the OP should try without authentication on the SMTP server. Leave password for POP though.  SignatureAdrian I use 2 servers. Both use authentication. In addition to that, Server1 uses SSL. The reason I know that I entered the correct values is that I could configure 3 email clients on the same machine (Mail, Thunderbird, Opera Mail) out of which only Mail.app refuses to work. I can freaking telnet to port 25 on the server and it works. The really frustrating thing is that I can't get any more detail on the error messages. The console doesn't say anything. I wish there was a way to debug this. -- nyenyec > > Did you in the Authentication option select "None" if it is true your > > ISP does not need authentication. [quoted text clipped - 5 lines] > without authentication on the SMTP server. Leave password for POP > though. I tried Mail/Window/Connection doctor. Here's what it said: Server1 (SSL + Auth): "Trying to log into this SMTP account failed. Please make sure the username and password are correct." I made sure. Server2 (Plain text auth) "Trying to log into this SMTP account failed. Please make sure the username and password are correct. Also verify that the server supports the Password authentication mechanism. If it does not, choose an appropriate authentication setting in the Advanced tab of the Account preferences." This is confusing. I thought that Accounts/Advanced was for the _incoming_ connection, not SMTP. If it's for SMTP then how do I set the 2 different ports? E.g. on Server1 my IMAP uses SSL + Port 993 and SMTP uses SSL on port 465. I guess the above suggestion to change those settings under the "Advanced" tab is misleading. -- nyenyec > The console doesn't say anything. I wish there was a way to debug this. > > -- nyenyec > I tried Mail/Window/Connection doctor. > [quoted text clipped - 21 lines] > guess the above suggestion to change those settings under the > "Advanced" tab is misleading. What does the system log file say? Use the Console app, select system.log and filter on "mail". SignatureTom Stiller PGP fingerprint = 5108 DDB2 9761 EDE5 E7E3 7BDA 71ED 6496 99C0 C7CF Nothing. It's empty. -- nyenyec > In article <1165265630.786262.62...@f1g2000cwa.googlegroups.com>, > [quoted text clipped - 30 lines] > PGP fingerprint = 5108 DDB2 9761 EDE5 E7E3 > 7BDA 71ED 6496 99C0 C7CF > > In article <1165265630.786262.62...@f1g2000cwa.googlegroups.com>, > > [quoted text clipped - 27 lines] > > > Nothing. It's empty. The log file is empty, or just when you filter on mail? SignatureTom Stiller PGP fingerprint = 5108 DDB2 9761 EDE5 E7E3 7BDA 71ED 6496 99C0 C7CF There is stuff in both the console log and the system log. When I filter for "mail" the system log has nothing and the console log has a few entries. 2006-12-04 14:06:22.430 Mail[192] 0x162770c0: observer lock is held, postponing release. break at /SourceCache/Message/Message-752.3/Utilities.subproj/FoundationAdditions.m:649 to debug 2006-12-04 15:03:29.441 Mail[470] Exception raised during monitored invocation of _fetchUnreadCountsCheckForNewMessages:, exception: *** -[NSConcreteData initWithBytes:length:copy:freeWhenDone:bytesAreVM:]: absurd length: -1, maximum size: -2147483648 bytes 2006-12-04 15:03:29.442 Mail[470] +[NSObject(LockingAdditions) clearLocks]: object 0x4ec290 still holds lock (count=1) in thread 0x199d400 2006-12-04 15:03:29.442 Mail[470] +[NSObject(LockingAdditions) clearLocks]: object 0x16972cb0 still holds lock (count=1) in thread 0x199d400 But these don't correspond to the sending attempts. When I try to send new mails, no log entries are generated even though I get the errors in the GUI. -- nyenyec > > > In article <1165265630.786262.62...@f1g2000cwa.googlegroups.com>, > > > [quoted text clipped - 35 lines] > PGP fingerprint = 5108 DDB2 9761 EDE5 E7E3 > 7BDA 71ED 6496 99C0 C7CF > There is stuff in both the console log and the system log. > When I filter for "mail" the system log has nothing and the console log [quoted text clipped - 18 lines] > new mails, no log entries are generated even though I get the errors in > the GUI. If this happened after a restart, it may indicate a problem with the Mail application. My console log shows only two mail related entries, each reporting the successful loading of a Mail plug-in. SignatureTom Stiller PGP fingerprint = 5108 DDB2 9761 EDE5 E7E3 7BDA 71ED 6496 99C0 C7CF > There is stuff in both the console log and the system log. You need to look at the log file on each smtp server. If you don't have the type of authority to view those logs, ask the person who does have the authority for assistance. In article <everyday-7EA7EB.12144204122006@newsclstr02.news.prodigy.com>, > > > Go to Mail / Preferences / Accounts / Outgoing Mail Server (SMTP) / > > > Server Settings / Authentication / select the option that fits your [quoted text clipped - 7 lines] > The error message is not bogus it's telling you that somewhere in your > setup you have entered the wrong information. Unfortunately, Mail's error messages are really poor, and it doesn't offer any session logging. What I've done when I've needed to troubleshoot Mail is use tcpdump from a Terminal window to capture the actual traffic. Do this in Terminal: sudo tcpdump -nx port 25 try to send mail using the non-SSL server, then type Control-C in the Terminal window to stop the capture, and post the output. SignatureBarry Margolin, barmar@alum.mit.edu Arlington, MA *** PLEASE post questions in newsgroups, not directly to me *** *** PLEASE don't copy me on replies, I'll read them in the group *** >"Cannot send message using the server (null)" >"SMTP server XXXX doesn't support authentication." Check the addres of the SMTP mail server. You might have a space or other character that is giving you the problem. I would applekey-a and press backspace and retype the mail server address in the SMTP server box. HTH, Keith So I've given up on this a month ago, but came back now and wrote a small Python program that stands between the SMTP server and the mail client and logs the traffic. I found tcpdump very hard to read. I compared the logs from mail clients that work (Opera, Thunderbird) and Mail.app, that doesn't. It seems, that Mail.app closes down the connection before even initiating the sending of the message: Client connected from: ('127.0.0.1', 56669) Connected to server XXXX on port 25 <<<<< server <<<<< 220 XXXX Microsoft ESMTP MAIL Service, Version: 5.0.2195.6713 ready at Sun, 31 Dec 2006 16:15:51 -0600 >>>>> local >>>>> EHLO [127.0.0.1] <<<<< server <<<<< 250-XXXX 250-TURN 250-ATRN 250-SIZE 250-ETRN 250-PIPELINING 250-DSN 250-ENHANCEDSTATUSCODES 250-8bitmime 250-BINARYMIME 250-CHUNKING 250-VRFY 250-TLS 250-STARTTLS 250-X-EXPS GSSAPI NTLM 250-AUTH GSSAPI NTLM 250-X-LINK2STATE 250-XEXCH50 250 OK Connection closed by ('127.0.0.1', 56669) This is where a normail client sends AUTH. I have no idea why Mail.app closes the connection at this point. I configured it to password authentication. I simply don't know where to go from here, other than doing random experimenting or using Outlook through Parallels. Any help is appreciated. -- nyenyec Ok, I finally found it. The key was to set NTLM authentication instead of password, since this was an Exchange Server. The other mail clients didn't make this distinction that's why I haven't paid attention to the setting. Cheers, nyenyec > So I've given up on this a month ago, but came back now and wrote a > small Python program that stands between the SMTP server and the mail [quoted text clipped - 48 lines] > > -- nyenyec > So I've given up on this a month ago, but came back now and wrote a > small Python program that stands between the SMTP server and the mail [quoted text clipped - 46 lines] > > Any help is appreciated. One of my users has a similar problem, with a wrinkle. He checks mail on two separate accounts on the same server. He has, as far as we can tell in the configuration screens, identical server information for both accounts. He can check mail on one account, but not the other. The only difference between the two accounts (besides the user names!) is that one has a small Inbox and the other (the one that fails) has a very large one. But, since the failure is before the actual Inbox is accessed, it's hard to know how this would make a difference. In the course of trouble-shooting, I found that Mail.app has a fixed (totally non-configurable) timeout setting, whereas other mail applications allow you to increase the timeout setting. If you want to experiment with other clients, Thunderbird is free and has pretty good IMAP support. There is a free version of Eudora as well; its IMAP support, at least the last time I used it, was not so great. So, I'd recommend Thunderbird. Give it a try, and let us know what you find. SignatureAF "Non Sequitur U has a really, really lousy debate team." --artyw raises the bar on rec.sport.baseball |
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