Mail refuses to send emails
nyenyec
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
Gerry
"nyenyec" <nye...@gmail.com> wrote:
Go to Mail / Preferences / Accounts / Outgoing Mail Server (SMTP) /
Server Settings / Authentication / select the option that fits your
service.
nyenyec
Gerry wrote:
>
> 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
Gerry
"nyenyec" <nye...@gmail.com> wrote:
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.
Adrian
> 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.
--
Adrian
nyenyec
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
nyenyec
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
Tom Stiller
"nyenyec" <nye...@gmail.com> wrote:
> 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.
What does the system log file say? Use the Console app, select
system.log and filter on "mail".
--
Tom Stiller
PGP fingerprint = 5108 DDB2 9761 EDE5 E7E3
7BDA 71ED 6496 99C0 C7CF
nyenyec
-- nyenyec
On Dec 4, 3:12 pm, Tom Stiller <tomstil...@comcast.net> wrote:
> In article <1165265630.786262.62...@f1g2000cwa.googlegroups.com>,
>
>
>
> "nyenyec" <nyen...@gmail.com> wrote:
> > 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.What does the system log file say? Use the Console app, select
Tom Stiller
"nyenyec" <nye...@gmail.com> wrote:
> Nothing. It's empty.
The log file is empty, or just when you filter on mail?
nyenyec
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
Tom Stiller
"nyenyec" <nye...@gmail.com> wrote:
> 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.
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.
Barry Margolin
<everyday-7EA7EB...@newsclstr02.news.prodigy.com>,
Gerry <ever...@sunrise.net> wrote:
> In article <1165262699.7...@79g2000cws.googlegroups.com>,
> "nyenyec" <nye...@gmail.com> wrote:
>
> > Gerry wrote:
> > >
> > > 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
>
> 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.
--
Barry Margolin, bar...@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 ***
Shawn Hirn
> 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.
Ke...@invalid.invalid
>"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
nyenyec
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
nyenyec
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
Alice Faber
"nyenyec" <nye...@gmail.com> wrote:
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.
--
AF
"Non Sequitur U has a really, really lousy debate team."
--artyw raises the bar on rec.sport.baseball