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Outlook 2007 error sending messages

Posted on 2011-09-04
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Running Outlook 2007 on a Windows XP platform, I am having a problem sending messages.  Messages are received OK.  The problem is happening with my laptop, and I am traveling away from home, using the wireless nework in a B&B where I am staying.  Outlook has three accounts, using three different SMTP servers, and none of them will send mail.  The error code is not consistent in every instance.  On a previous attempt it was 0x800CCC6F, and just now it was 80042109. Outlook error
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Question by:ddantes
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by:John Hurst
ID: 36481663
For sending, Outlook has to have: the correct email address, the correct smtp address, the correct ports and, most likely, authentication for the sender (in the advanced account setup).

My guess is that you are not authenticated to send on these external (foreign) networks. This is extremely common and happens to me.

I solve this problem by having portable sending accounts that require authentication. Others solve it by getting an account where they travel to if they travel frequently to that location. There is more than one way to do this, but it must be tailored to you.

... Thinkpads_User
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by:BobintheNoc
ID: 36481960
Additionally, many ISPs block outbound port 25 connections (for smtp) to foreign servers.  Often, they require that you relay from their SMTP server.

How about firewall--do you have it enabled and if so, a rule to allow outbound port 25?

The smtp address--is it an FQDN or an IP address?

In any case, to verify actual connectivity to your preferred smtp server, and that it actually is your server:  use telnet from a cmd prompt:  example:  cmd....Telnet my.server.smtp 25    (telnet: launches the telnet app/client; my.server.smtp:insert your smtp server IP or FQDN, then 25:represents the port to use.

When you hit enter, hit enter a couple times.  If you get a blinking cursor at the top, you've connected to something, otherwise you'll get an error about not being able to connect.  If you connect, try hitting enter--you should get  a banner from your smtp server identifying it.  Type HELO or EHLO to begin a communications..
If you get this far, you know that you're not being blocked via firewall, and that you've got the right address info.



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by:John Hurst
ID: 36481969
I never had firewall issues with foreign connections (foreign to the home connection), merely authentication issues (the home ISP does not know it is you without authentication). Firewall comes up 1% of the time, authentication comes up the other 99% of the time. ... Thinkpads_User
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by:ddantes
ID: 36482058
Thank you for your comments.  Regarding the Telnet test, I'm not clear what to type. For example, in the case of smtp.maui.net, what shall I type?
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by:John Hurst
ID: 36482075
It depends on what your mail server responds to . I got a response on my own mail server using:

telnet mailserver.com 110  .

... Thinkpads_User
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by:ddantes
ID: 36482134
Sorry, I'm afraid I don't know how to implement this protocol.   I know the smtp server name, but not the IP address, and I am not familiar with FQDN.
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Psyadi earned 125 total points
ID: 36482443
for easy of travel you should maybe get yourself a mobile broadband connection. this will allow you set your outgoing servers to the mobile device and never have to worry about authentication, regardless of where you are.

If you are on a network at the B&B that the provider has blocked outgoing mail from anything except their servers then you wont be able to send mail out from your laptop by any method except via their servers.
You can always change the outgoing servers to be the B&B ISP's outgoing servers and this should solve your problem (you wont need to authenticate as you as already connected to the network).
To do this you will need to find out who their ISP is and then google the outgoing mail servers for that ISP.

When traveling it is always easier to have a mobile broadband device for this type of thing.
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by:BobintheNoc
ID: 36483194
Open a CMD window, by clicking START...RUN. and Type CMD, then hit enter.

Type "telnet smtp.maui.net 25"  without the quotes and hit enter a couple times.

If nothing responds, you'll get an unable to connect type message.  If you DO get a connection, usually, the CMD window will clear, and flash an underscore type cursor at the top left corner.

If nothing pops onto the screen within a few seconds, hit ENTER again, the type "HELO" and hit enter

If you get the SMTP Mail server's smtp service, you'll likely see a banner from the server, just a line or two of text, identifying itself and probably saying something like Hello back to you.

This will confirm that SMTP is on and responding on TCP Port 25.  If you want to send a mail message to someone on that server's users' email address, you can manually craft one at this point by type each of these lines, exactly, except substituting valid email addresses in the spots as indicated.  Everything below between the lines of asterisks
:
******************
mail from: youremail@yourdomain.com  
rcpt to: someone@thisdomain.com
DATA
Hello Someone,
Test Line Two of Message body
Hit Enter    <------(don't type HIT ENTER, just hit the enter key)
.             <-----------That's a period, just a single period, then hit enter a couple times
**********************
If you typed it right, and the email addresses you use are proper, you should get a notice that the message was received or queued or something.  And then you can exit/quite by typing exit or quit and hitting enter.

This will have placed a very small email message into the SMTP server's inbound Q.

Now, back to your problem-- after you type the TELNET smtp.maui.net 25 line, if you get Connecting to smtp.maui.net...  and eventually get " Could not open connection to the host, on port 25: Connect failed ", either the DNS name you entered for the mail server is incorrect, or perhaps something is preventing your access to that destination over that TCP port.

If you get just a blinking line on the screen (underscore cursor), and no response at all, even after hitting enter a few times, and then you get dumped right back to your cmd prompt, it may be the ISP that's implementing some security mechanism, like a blackhole for tcp port 25 (usually used for SMTP mail).  This is more common within residential ISP providers, like your local cable modem company or dsl provider.  In this case, it's likely that they'll only allow you to connect to THEIR smtp server to relay mail to other domains.  This gets a little trickier to setup, but still very doable.

After you've confirmed or denied the actual live ability to directly connect to the smtp server, you need to confirm whether or not the server will allow you to send mail with or without an account from that server.  If you send to an email address within maui.net, it's likely that you wouldn't need an account, as this server may likely be the main smtp server for the company.  If you are trying to send email to another domain that smtp.maui.com doesn't "own", that'd be a relay delivery---which most servers DO require an account and password.  You'll have to check with the mail admin at maui.com to find out for sure.

Let us know if you can successfully start a TELNET session to your server, and we'll go from there.

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by:John Hurst
ID: 36483575
With respect to all, I don't see this (initially at least) as a telnet exercise or a firewall exercise. I travel a lot and have had the issue posted at the top.

ddantes - You should start with your ISP and ask if they have an SMTP server you can use when travelling. That would be a big start. It may not work everywhere, but at least you would have some success. It means setting up a new account and putting in the correct variables (email address, smtp address, port numbers and authentication). Assuming this works, you can have one (or more accounts just for sending when travelling.

Psyadi offers a very good suggestion to use a mobile broadband key. I use one myself, but they do cost money.  Still, it is a good idea, and it is much cleaner than the multiple sending account idea.

... Thinkpads_User
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Author Comment

by:ddantes
ID: 36484715
I appreciate all experts' comments.  The B&B owner contact his tech support and they provided instructions for temporarily changing my Outlook accounts SMTP settings.
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by:BobintheNoc
ID: 36485399
The telnet reference is purely a troubleshooting mechanism to determine if you can actually reach the SMTP server.   If a firewall or restriction policy is in place on a network, using telnet to verify basic connectivity is a common practice amongst engineers/admins.

As a road-warrior, it's important to know your alternatives in the event that your primary method doesn't function on a network.  Hopefully, your email service has a web accessible interface, like mail.yahoo.com, mail.google.com or your exchange servers Outlook Web Access.  You can always count on HTTP/HTTPS being functional on just about any network that's intended to be used by travelers.

The shift to blocking things other than port 80/443 (http/https) combined with the problems of administering a traditional pptp/ipsec VPN have led many organizations to use SSL based vpn connections--  VPN that will work over the 80/443 that most public networks provide.  With SSL VPN, you get compatibility, portability and consistency.
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