mail sent but never arrives

[drschenck]

entourage appears to be sending my mail, but after receiving no replies
to a few e-mails i sent it appears that my sent mail is not arriving.
the last e-mail that i know was received was sent dec 12th. the first
e-mail that didn't make it was sent dec 14th. i have no clue what could
have changed with entourage during that time. i can send and receive
e-mail using webmail.

i was running version 10.0.0, but just now updated to 10.1.6 with no
apparent change in performance.

any thoughts would be greatly appreciated.

 

[Barry Wainwright [MVP]]

entourage appears to be sending my mail, but after receiving no replies
to a few e-mails i sent it appears that my sent mail is not arriving.
the last e-mail that i know was received was sent dec 12th. the first
e-mail that didn't make it was sent dec 14th. i have no clue what could
have changed with entourage during that time. i can send and receive
e-mail using webmail.

i was running version 10.0.0, but just now updated to 10.1.6 with no
apparent change in performance.

any thoughts would be greatly appreciated.

If you haven't received an error message or a bounce announcement, then the
mail is 'in the system'[ somewhere. You do realise that mail can
legitimately take 3 days to be delivered? It could well be held in a queue
on an intermediate mail server somewhere. If that server can't pass the
message on to the next one in the chain, it will generate a delivery failure
message that will be relayed back to you.

 

[drschenck]

thanks, barry.

i don't think that it's a delay 'in the system' though - no error
messages, no delivery failure messages. i almost instantly receive
e-mail i send to myself from webmail. i send e-mail using other
accounts with entourage and it never arrives. i've sent over 16 e-mails
using entourage since dec 14th and none have arrived, yet every e-mail
i send using webmail arrives within seconds . . .

is it possible that my outgoing mail is being redirected by some
malicious software on my machine (which is a mac, btw)?

 

[Barry Wainwright [MVP]]

I haven't heard of any malware for the mac that could have those symptoms
though - what do you have in the 'sending mail server' account settings.

--
Barry Wainwright
Microsoft MVP (see http://mvp.support.microsoft.com for details)
The Entourage User's WebLog has moved!
For hints, tips and troubleshooting go to <http://www.barryw.net/weblog/>

From: drschenck <[email protected]>
Organization: http://groups.google.com
Newsgroups: microsoft.public.mac.office.entourage
Date: 24 Dec 2006 06:02:40 -0800
Subject: Re: mail sent but never arrives

thanks, barry.

i don't think that it's a delay 'in the system' though - no error
messages, no delivery failure messages. i almost instantly receive
e-mail i send to myself from webmail. i send e-mail using other
accounts with entourage and it never arrives. i've sent over 16 e-mails
using entourage since dec 14th and none have arrived, yet every e-mail
i send using webmail arrives within seconds . . .

is it possible that my outgoing mail is being redirected by some
malicious software on my machine (which is a mac, btw)?

On 23/12/06 22:45, in article
(e-mail address removed), "drschenck"

If you haven't received an error message or a bounce announcement, then the
mail is 'in the system'[ somewhere. You do realise that mail can
legitimately take 3 days to be delivered? It could well be held in a queue
on an intermediate mail server somewhere. If that server can't pass the
message on to the next one in the chain, it will generate a delivery failure
message that will be relayed back to you.

--
Barry Wainwright
Microsoft MVP (see http://mvp.support.microsoft.com for details)
The Entourage User's WebLog has moved!
For hints, tips and troubleshooting go to <http://www.barryw.net/weblog/>

 

[drschenck]

I haven't heard of any malware for the mac that could have those symptoms
though - what do you have in the 'sending mail server' account settings.

--
Barry Wainwright
Microsoft MVP (see http://mvp.support.microsoft.com for details)
The Entourage User's WebLog has moved!
For hints, tips and troubleshooting go to <http://www.barryw.net/weblog/>

in tools>accounts> the smtp server is mail.insightbb.com and in
"advanced sending options" nothing is checked. i've tried checking the
"requires secure connection" and "requires authentication" boxes, but
then i get an error when i try to send mail. checking the "override"
box seems to have no effect.

 

[William Smith]

in tools>accounts> the smtp server is mail.insightbb.com and in
"advanced sending options" nothing is checked. i've tried checking the
"requires secure connection" and "requires authentication" boxes, but
then i get an error when i try to send mail. checking the "override"
box seems to have no effect.

Email can be delayed or lost in several places. Most will not be in your
control.

You've already done some troubleshooting and found that your webmail
(I'm assuming you're accessing the same account you're using in
Entourage) gets received but your Entourage-sent mail doesn't get
received. Possibly something is wrong with your SMTP server. If you
receive no error messages when sending then your SMTP server is indeed
receiving your message. At that point your ISP must track your message
for you.

Here's some more troubleshooting ideas:

1. Send a message through Entourage from yourself to yourself. You can
use the same account as the sending and receiving accounts. Do you get
something back?

2. Are you sending messages to large groups of addresses? Some ISPs
limit the number of recipients you can send a single message to as a
means of preventing spam.

3. Sign up for a free POP/SMTP account temporarily and test sending
through it. Google's Gmail allows you to access an account via Entourage
and other applications.

4. Set up Apple's Mail application to access the same account you're
troubleshooting. Do you get the same results?

bill

 

[Diane Ross]

in tools>accounts> the smtp server is mail.insightbb.com and in
"advanced sending options" nothing is checked. i've tried checking the
"requires secure connection" and "requires authentication" boxes, but
then i get an error when i try to send mail. checking the "override"
box seems to have no effect.

Verify that mail.insightbb.com is the correct SMTP server. Check to see that
you have spelled it correctly and that there are no spaces at the end. I
would just try SMTP.insightbb.com to see if that works.BTW, have you ever
been able to send with this account in Entourage or another mail app? When
you entered the account info, did you click on verify? What happened. Have
you tried deleting (not erasing info) the account and creating a new one
from scratch?

If you want to look under the hood so to speak, you can monitor the traffic
between Entourage and your ISP. Use tcpflow:

Download the Mac OS X version here:



<http://www2.entropy.ch/download/tcpflow-0.21.pkg.tar.gz> (Panther)



<http://www2.entropy.ch/download/tcpflow-0.20-jaguar.pkg.tar.gz> (Jaguar)



When you install, you do not see it.

To run the test, quit all other apps
that might be connecting to the internet like your browser, ftp client.



Copy/paste in this command in the Terminal:

sudo /usr/local/bin/tcpflow -i en0 -c



Now try to send the email and watch the traffic in the window of the
Terminal. You should see what is failing.

Here is an example with passcode info xxxx out.

Last login: Sun Dec 24 15:22:37 on ttyp1
Welcome to Darwin!
diane-ross-power-mac-g4:~ diane$ sudo /usr/local/bin/tcpflow -i en0 -c
Password:
/usr/local/bin/tcpflow[530]: listening on en0
204.127.198.010.00110-192.168.001.104.49747: +OK (rwcrpxc56) Maillennium
POP3/PROXY server #90

192.168.001.104.49747-204.127.198.010.00110: USER diane.ross

204.127.198.010.00110-192.168.001.104.49747: +OK

192.168.001.104.49747-204.127.198.010.00110: PASS xxxxxxx

204.127.198.010.00110-192.168.001.104.49747: +OK ready

192.168.001.104.49747-204.127.198.010.00110: UIDL

204.127.198.010.00110-192.168.001.104.49747: +OK 0 messages (0)
..

192.168.001.104.49747-204.127.198.010.00110: QUIT

204.127.198.010.00110-192.168.001.104.49747: +OK comcast.net

--
Diane Ross, Microsoft Mac MVP
Entourage Help Page
<http://www.entourage.mvps.org/>
The Entourage Blog lists the EHP as one of the top five Microsoft Entourage
resources.
<http://blogs.msdn.com/entourage/>