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bricar1Flag for United States of America

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Outlook mail will receive but not send for 3 users out of 30 in domain environment

Email for all 30 users in our domain has been working flawlessly for years. We do not use exchange server... each machine does Outlook email on its own.

A week ago, all of a sudden 3 of our 30 users could not send email. It says that the mail server is "unreachable". I have a choice of using optimum online's smtp server or our own. Everybody, for years has been set up to use optimum's email server. Never a problem.

For these three, I tried our own outgoing server (we successfully use this for all our wireless phones, again never a problem). I spent 2 hours with our hosting company, HostGator (I know... :/  ), they guy looked at every possibility that he was aware of and couldn't come up with anything. He insists that these three users are not blocked in any way.

Our email convention is firstname.lastname@domain.org. I created a new email for one user in cPanel with the convention firstname_lasname@domain.org. Same thing.. no ability to communicate with the new email address.

Network is set up with standard 192.168.1.xxx routing. Problem exists whether address is static or assigned via DHCP.

I'm really stumped on this one. 3 computers out of 30 overnight, and there is no common network architecture. One computer is on the first floor and the other two are on the second floor.

Users are able to send email in their webmail portal provided by HostGator.

Can someone please help me troubleshoot this issue?

Thanks!

Windows 7 Pro workstations
Server - Windows Server 2008 R2
No Exchange, each workstation is independent
All firewalls deactivated, Symantec Endpoint Security deactivated
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John
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For one user as a test, make sure you know the Email account, backup the PST file (for safety), go to Control Panel, Mail, and remove (delete) the Outlook Profile.

Restart the computer, open Outlook, create a new profile, set up the account and test.
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I'm pretty sure I did that but I'm going back today and will tray it again as at this point I need to start from scratch. I'll report back my findings. Thanks.
If a new Outlook Profile does not work on one of the problem machines, set up a new, test, Windows User Profile (Account). Log into the new Account and try Outlook in the new Windows Account.
"host unreachable" seems more like a routing or network problem to me.
Can you ping the smtp server(s)? If they usually answer to ping, do they answer to ping on the PCs whose users cannot send email?
Have you checked the SMTP protocols settings? Are you using SSL/TLS? If so is it on all the accounts? With the same settings, including ports?
Do you use client certificates?
Are the PCs' internal clocks synchronized?
check for authentication mode for out going emails from Outlook settings for these users

File -- Account Settings -- select the account "Change" -- more settings -- Outgoing servers tab.
select these options:
--my outgoing server (SMTP) requires auth
-- --Use same settings as my incoming mail server
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ASKER

Authentication in Outlook settings has been changed with every combination imaginable.

I will be going onsite tonight to renew my efforts on the situation. From my home I can ping the domain's outgoing mail server, but not Optonline's. First thing I will do it try to ping the server.

Very unusual that overnight three unrelated computers exhibited the same behavior, all with precisely the same settings that are used on all 30 PCs. First time I've ever run into something like this.

Assuming I CAN'T ping the outgoing server, what would be some possible causes for the blockage, considering that there are no firewalls running. The PCs all plug into a Cisco router and nothing more. I'm beginning to think the answer may lie within the router, although why it would selectively block three users simultaneously is beyond me at this point.
You do need to try a new Outlook Profile and new Windows Account on one problem computer. A small virus outbreak could cause the Windows Account issues.
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I just arrived onsite and created a new Windows account. Currently I'm creating a new outlook profile.

FWIW, I can indeed ping the mail server from these three machines. Will report back shortly.
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Action:
Created a new Windows account. Created a new Outlook profile. Able to ping outgoing server via cmd.

Result:
Same issue. Here's the error message:
"Error 0x800CCC0D - Cannot find the email server. Verify the server information in your account properties."

Naturally I checked smtp settings and tried both mail.ourdomain.org and the optonline smtp server. Same result for both.

I did try a system restore last week, restoring to a period well prior to this issue. No effect.

I'm going to have to look at the router.
If other users are sending mail through the same router (is this true?) it would seem not to be the router unless you are blocking by individual user
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My thoughts exactly. I thought maybe something went rogue in the router and it started selectively blocking.

I just set up an IMAP account on my test profile (instead of the usual POP3) and I successfully sent email out.

I'm going to convert the real user to IMAP and see what happens. I'll report back.
I thought maybe something went rogue in the router  <-- That is possible. You could try resetting the router.
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At this point I'm afraid of opening up a can of worms by resetting the router.

I've been successful with IMAP, but no matter what I do I can't seem to end up with only one profile showing in folder view. In other words, 2 data files are always associated with the new IMAP account. I cannot change the default data file. Default always remains the one it chose for itself, and I have no way of "closing" the secondary folder.

Is there a quick way I can start clean and end up with one profile and one data file? I always end up with the two.
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In other words, in the folder view there is always another account showing and there is no option in the sub-menu to "close" it.
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John
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Thanks, John. I absolutely will look at the router in the future. Right now there's a lot of craziness going on here with a board meeting and a possible merger, so I can't play with the router tonight.

I created a new user account on the network and then set up Outlook again. All is well at this point. I had to fast-track things tonight. I'm going to leave the other two PCs as-is tonight and tackle the router next time I'm in. At least I got Human Resources going which was the important one.
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Should I leave this question open for the week since I'll be back in a day or two or should I close it out?
If you think we have solved the problem (looks like we have) then you should probably close it out.
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Just for the sake of others who may read this in the future, I'm not sure how to close this out. My temporary solution was to switch to IMAP, while the original issue is still unresolved.= in terms of identifying what exactly is blocking pop3 and why.

I have no problem closing it and awarding points for all your help, which is very much appreciated... I'm just not sure we clearly identified the actual problem. Again, just for the sake of someone happening upon this thread looking for an answer. Thoughts?
You said "I created a new user account on the network and then set up Outlook again. All is well at this point" I asked you to create a new Outlook Profile which entails (enforces) making a new account.

So I think I have helped you to a solution.
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You have.. I explained my result badly due to fatigue. I had to stick with IMAP as pop3 stayed blocked no matter what I did. Thanks a million for all your help!
Thank you for the update and I was pleased to help you.
Just ran into this and if this is redundant please forgive. If you had POP which was not able to connect and you fixed by switching to IMAP and assuming this was the "fix", then this would point to a port issue. They use different default ports (POP 110 or SSL/TLS 995) and (IMAP 143 or SSL/TLS 993). Whether this was a router issue, an ISP in the middle issue, or a mail server issue I don't know. However, switching from POP to IMAP is always a good move where IMAP is an option.