Entourage 2008 sending mail fails first time but never second

[Chris Bailey]

Got a curious problem here. I use Entourage 2008 (12.1.2) and have 12
accounts setup for sending and receiving. I have a problem with sending
messages from two accounts I have hosted by GoDaddy. The way GoDaddy is
setup, all outgoing messages go through the same SMTP conduit
(smtpout.secureserver.net). You can either use port 25, 80 or 3535
(their own custom port, I guess), or you can enable SSL and use port
465.

If I enable SSL and use 465, virtually every time I send a message,
Entourage immediately barfs on it and gives me this message:

Entourage cannot find the server. Verify the server information is
entered correctly in the Account Settings, and that your DNS settings
in the Network pane of the System Preferences are correct. Mail could
not be sent. Account name: "myaccount". Error: -3170

If I use ports 80 or 3535 (haven't tried 25 but I try to avoid that
port anyway since some networks I connect to block it), the symptom is
similar. The first attempt sort of hangs... if you open Entourage's
progress window, you'll see it attempting to connect to the SMTP host
but getting nowhere. If you cancel it and try to send it again, it goes
through 99% of the time on the second attempt.

This isn't limited to my machine. I have a couple of clients who are
also using the same version of Entourage and the same GoDaddy host, and
we all have the same problem (two of us use a regional ISP for our
Internet service, and the third uses AT&T, so I'd say the ISP can
probably be ruled out).

I'm leaning toward thinking this is a GoDaddy issue, but of course they
say nothing is wrong. Yet this has been going on for months. We're
getting tired of having to send each and every message twice... I'm
tempted to move one of my clients or myself to a new host just to see
if that makes it go away. Another reason I lean toward GoDaddy as the
problem is that the other 10 accounts I have that are not hosted by
them do not experience this problem, although I pretty much only use 2
of those accounts to actually send mail... the other 8 are usually just
for mail I receive, and I don't reply to them usually.

Any suggestions? Has anyone else run into this with other hosts? Or can
someone who uses GoDaddy's SMTP host tell me they also experience the
same problem?

Thanks for your time.

Charles "Chris" Bailey
Benton Harbor, Michigan

 

[Diane Ross]

that your DNS settings
in the Network pane of the System Preferences are correct. Mail could
not be sent. Account name: "myaccount". Error: -3170

<http://www.entourage.mvps.org/error/number.html#error-3170>

The newest release 10.5.5 is supposed to improve the DNS issues.

This has become a common problem lately in the past several months and
is out of Microsoft's control.

Your ISP's DNS servers, which resolve server names to IP addresses so
that your machine can connect, have given your Mac some bad information.

First, try clearing your computer's DNS cache. It's quick and causes no
Harm:

1. Open the Terminal application found in /Applications/Utilities.
2. Enter this command followed by a return:

dscacheutil -flushcache (for Leopard)
lookupd -flushcache (for Tiger)

3. Try your download again. Your machine should have to query your DNS
servers again for an address.

If the above doesn't work then your ISP's DNS servers are still causing
you a problem. Look into using <http://www.opendns.org/> to substitute
your ISP's DNS server addresses with this service's DNS servers. It's
also very simple and will very probably allow you to download your
updates. You may need to run the above Terminal command again after
changing your DNS servers.

You might also consider just using these new DNS server addresses
permanently. See if your speed accessing websites improves and note
whether or not you have fewer or more problems connecting to sites.

For more information have a look at this blog post:

"Unable to download updates"
<http://blog.entourage.mvps.org/2008/07/unable_to_download_updates.html>

In case the above link does not work:

<http://tinyurl.com/6x98s3>

Hope this helps!

 

[siamesekitten]

Hi Diane,
Thanks for the helpful message. However, I have the same problem, but it
only started this weekend after I finally upgraded from Office 2004 to Office
2008 on Friday night. So it is definitely a Microsoft issue, not a system or
network issue. About one time out of six, sending mail will fail with an
error. I then click Send All again and it goes. I have rebuilt the database
and applied all updates. My MacBook Pro system is also the very latest with
all updates

Today's error log shows that 6 messages (out of 36 I've sent today) had to
be resent before they would go out. This is the error message for all of them:
Connection to the server failed or was dropped.
The server is not responding.
Account name: "Mac.com"
Error: -17895

I never had this error before installing Office 2008.
Any ideas?

Thanks!

 

[siamesekitten]

PS Some more information:

My send mail server for the Mac.com POP account referenced in the error
message is AT&T Yahoo DSL:

smtp.att.yahoo.com

I am using authenticated sending with SSL on port 465, as specified in
AT&T's setup instructions.

 

[Diane Ross]

My send mail server for the Mac.com POP account referenced in the error
message is AT&T Yahoo DSL:

See if these instructions help. Entourage 2008 just like Leopard have more
security features.

AT&T Yahoo - New Security Settings
<http://www.entourage.mvps.org/accounts/att_yahoo.html>

We have several AT&T settings for accounts. See this page if the above is
not your setup.

AT&T/Yahoo
AT&T (formerly BellSouth)
AT&T Worldnet
AT&T Yahoo
Sympatico Account
Yahoo
Yahoo Plus

Accounts <http://www.entourage.mvps.org/accounts/index.html>

 

[siamesekitten]

Hi Diane,
I appreciate the reply, but I don't have any authentication issues. What I
have is frequent timeout problems connecting to the SMTP server that did not
exist until I upgraded to 2008 from 2004 a week ago. I have exactly the
settings cited in your first link, and no problems at all receiving mail,
only sending.

The error message I get is:
Connection to the server failed or was dropped.
The server is not responding.
Account name: "XYZ"
Error: -17895

Again, I have been using this account for years in 2004 with no problems.
Only on upgrading to 2008 am I suddenly getting these connection errors.

Thanks

 

[Ed Kimball]

Hi Diane,
I appreciate the reply, but I don't have any authentication issues. What I
have is frequent timeout problems connecting to the SMTP server that did not
exist until I upgraded to 2008 from 2004 a week ago. I have exactly the
settings cited in your first link, and no problems at all receiving mail,
only sending.

The error message I get is:
Connection to the server failed or was dropped.
The server is not responding.
Account name: "XYZ"
Error: -17895

Again, I have been using this account for years in 2004 with no problems.
Only on upgrading to 2008 am I suddenly getting these connection errors.

Thanks

"Connection to the server failed ..." can indeed be an authentication issue.
Double-check your settings.

 

[Fernando Rivas]

I've been having the same problem since I first installed Leopard. It seems like an incompatibitiy issue between Entourage and Leopard. When I installed the latest Leopard update Entourage sent mail fine the first few times then reverted back to the quit and send again syndrome. I also use GoDaddy however and have my doubts about the interaction there. Anyone have any suggestions? Clearing the DNS caches doesn't sound like the way to go.

 

[Diane Ross]

I've been having the same problem since I first installed Leopard. It seems
like an incompatibitiy issue between Entourage and Leopard. When I installed
the latest Leopard update Entourage sent mail fine the first few times then
reverted back to the quit and send again syndrome. I also use GoDaddy however
and have my doubts about the interaction there. Anyone have any suggestions?
Clearing the DNS caches doesn't sound like the way to go.

What type of account? (POP, IMAP, Exchange)

 

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[Anita Brightman]

I get the same error message on my mac. I also use Entourage 08. In addition to the error with my email account, I can't get my iphone to get messages either. ANY SUGGESTIONS?

Got a curious problem here. I use Entourage 2008 (12.1.2) and have 12
accounts setup for sending and receiving. I have a problem with sending
messages from two accounts I have hosted by GoDaddy. The way GoDaddy is
setup, all outgoing messages go through the same SMTP conduit (smtpout.secureserver.net).
You can either use port 25, 80 or 3535 (their own custom port, I guess),
or you can enable SSL and use port 465.





If I enable SSL and use 465, virtually every time I send a message, Entourage
immediately barfs on it and gives me this message:





Entourage cannot find the server. Verify the server information is entered
correctly in the Account Settings, and that your DNS settings in the Network
pane of the System Preferences are correct. Mail could not be sent. Account
name: "myaccount". Error: -3170





If I use ports 80 or 3535 (haven't tried 25 but I try to avoid that port
anyway since some networks I connect to block it), the symptom is similar.
The first attempt sort of hangs... if you open Entourage's progress window,
you'll see it attempting to connect to the SMTP host but getting nowhere.
If you cancel it and try to send it again, it goes through 99% of the
time on the second attempt.





This isn't limited to my machine. I have a couple of clients who are also
using the same version of Entourage and the same GoDaddy host, and we
all have the same problem (two of us use a regional ISP for our Internet
service, and the third uses AT&T, so I'd say the ISP can probably be ruled
out).





I'm leaning toward thinking this is a GoDaddy issue, but of course they
say nothing is wrong. Yet this has been going on for months. We're getting
tired of having to send each and every message twice... I'm tempted to
move one of my clients or myself to a new host just to see if that makes
it go away. Another reason I lean toward GoDaddy as the problem is that
the other 10 accounts I have that are not hosted by them do not experience
this problem, although I pretty much only use 2 of those accounts to actually
send mail... the other 8 are usually just for mail I receive, and I don't
reply to them usually.





Any suggestions? Has anyone else run into this with other hosts? Or can
someone who uses GoDaddy's SMTP host tell me they also experience the
same problem?





Thanks for your time.





Charles "Chris" Bailey Benton Harbor, Michigan

 

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