Operation on server timed out...cannot send mail

[Sasabridge]

Version: 2008
Operating System: Mac OS X 10.5 (Leopard)
Processor: Intel
Email Client: pop

This started happening a few weeks ago when I sent messages with attachments, they would take forever and then time out. Sometimes, eventually, they would send. Then it was any size attachment. Now even a simple message with NO attachment won't send! It just hangs forever in my outbox.

I checked every other factor and it has to be an Entourage problem. Changed the port and that didn't do anything.

I'm able to receive messages just fine.

Help!!

An operation on the server timed out. The server may be down, overloaded, or there may be too much net traffic.

 

[William Smith [MVP]]

This started happening a few weeks ago when I sent messages with
attachments, they would take forever and then time out. Sometimes,
eventually, they would send. Then it was any size attachment. Now
even a simple message with NO attachment won't send! It just hangs
forever in my outbox.

I checked every other factor and it has to be an Entourage problem.
Changed the port and that didn't do anything.

I'm able to receive messages just fine.

This doesn't necessarily have to be Entourage.

Set up your account in Apple's Mail application and test sending from
there. If you have problems sending then this may be because of your
network or it may be your mail server.

If you have a second computer then set up your account in any E-mail
application there and see what happens.

If you are using a laptop then move away from your current network and
go to a local coffee shop or wireless hotspot. If mail works there then
your network is the problem.

Hope this helps!

--

bill

Entourage Help Page <http://entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
YouTalk <http://nine.pairlist.net/mailman/listinfo/youtalk>
Twitter: follow <http://twitter.com/meck>

 

[Sasabridge]

Hi Bill,

I tried sending in Thunderbird, Mail, and online through my webmail and all work fine. I also have access to a second computer (uses gmail) on the same wireless network (my roommate) and she has no problems sending mail. I also called my hosting provider (Media Temple) and they talked me through tech support for almost an hour. They knew immediately it wasn't a problem with hosting and was able to help me identify it as an Entourage problem.

When I use my laptop at a local coffee shop it still gets stuck in Entourage.

I would like to continue using Entourage. I really love it! And I really don't like any other email program.

When I google this problem I see that it's common. Suggestions have been offered but, similar to my situation, none have been the solution. I haven't been able to find a fix for this! I'm not ready to give up! Please help!!

Thank you so much,
Saundra

 

[William Smith [MVP]]

I tried sending in Thunderbird, Mail, and online through my webmail
and all work fine. I also have access to a second computer (uses
gmail) on the same wireless network (my roommate) and she has no
problems sending mail. I also called my hosting provider (Media
Temple) and they talked me through tech support for almost an hour.
They knew immediately it wasn't a problem with hosting and was able
to help me identify it as an Entourage problem.

When I use my laptop at a local coffee shop it still gets stuck in
Entourage.

Your troubleshooting seems right on the mark. I'd just like to get a
little more confirmation.

Does Entourage have problems with a specific account or with sending any
E-mail from accounts from different providers? You mention Media
Temple. Are you having problems with a Media Temple hosted account? Do
you have a second account on your machine such as Gmail or Hotmail that
is set up to send through their servers and not through Media Temple's
servers? Do both accounts fail or just one?

Using the information I'm finding here
<http://kb.mediatemple.net/questions/522/How+can+I+setup+email+in+Outlook+2007?>,
your SMTP (Sending mail server) settings should be:

server: mail.my-domain-temple.net (assuming you use your domain)
requires authentication: true
use same authentication settings as receiving mail server: true

Nothing else indicates you need to use a special port or SSL.

Is this what you have now?

An alternative shown on the same page:

server: mail.my-domain-temple.net (assuming you use your domain)
requires authentication: true
use same settings as receiving mail server: true
override outgoing port: true
port number: 587

Port 587 is an alternative to port 25, which is the default in
Entourage. Have you tried this?

--

bill

Entourage Help Page <http://entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
YouTalk <http://nine.pairlist.net/mailman/listinfo/youtalk>
Twitter: follow <http://twitter.com/meck>

 

[Sasabridge]

Hi Bill,

To answer your last two questions first, I rechecked my SMTP settings and they are correct. I tried port 587 as an alternative to port 25 and it made no difference.

So I just created a gmail account and tried to send a 32kb attachment to myself from there. My roommate uses gmail and claims to have no problems sending mail or attachments. The interesting thing that happened is that I also got an error. (Oops...a server error occurred and your email was not sent. #6502). But it actually did send because I received it and it went into my "Sent Mail" folder. A second test got stuck--no error message but it wouldn't send. (Gmail just says "still working" for 10 min until I cancelled). A third test (all with the same 32kb attachment) gave me a different error. It just said "attachment failed."

I am hopeful! What do you think?

 

[Sasabridge]

Hi Bill,

One more thing. I retested sending messages through my webmail (SquirrelMail) and Thunderbird, because they worked the last time I tested. Here's what happened.

SquirrelMail took a long time but the email sent. This was from myself to myself. A second attempt from myself to my new gmail account failed.

This time Thunderbird failed, it got stuck at 82%.

Maybe it was just a fluke that they worked last time I tested?

Thanks so much

 

[William Smith [MVP]]

One more thing. I retested sending messages through my webmail
(SquirrelMail) and Thunderbird, because they worked the last time I
tested. Here's what happened.

SquirrelMail took a long time but the email sent. This was from
myself to myself. A second attempt from myself to my new gmail
account failed.

This time Thunderbird failed, it got stuck at 82%.

Maybe it was just a fluke that they worked last time I tested?

Hmm... Good information. I'm still not 100% convinced Entourage is the
problem.

The "Oops...a server error occurred and your email was not sent. #6502"
error message is coming from your ISP, I believe. That's not an
Entourage error message. From what I read online, folks have seen the
same error message from Google Mail as well.

You mention having a roommate and I suspect your roommate has a second
computer. That tells me you're probably using a router or wireless
access point.

Are you using wireless? If so, try simply restarting it and see if
things improve. You can also test sending by plugging your computer
directly into the router using an Ethernet cable. You can find one at
any computer or electronics store like Best Buy for under $10.00.

Also, are you connecting via cable modem or DSL? I suggest also
restarting this device as well, just to make sure.

--

bill

Entourage Help Page <http://entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
YouTalk <http://nine.pairlist.net/mailman/listinfo/youtalk>
Twitter: follow <http://twitter.com/meck>

 

[Diane Ross]

This time Thunderbird failed, it got stuck at 82%.

Are you using the same attachment each time? I would test with a different
attachment to be sure.