Cannot connect to SMTP servers from Windows 2008 R2 Server.

cerksees
cerksees used Ask the Experts™
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I cannot connect to any SMTP servers from my Windows 2008 R2 Server.

I cannot telnet to a server.  I even installed Thunderbird and it cannot connect to the server.

I know the server credentials and email account details are correct as I used them to connect from my Win7 machine without incident.

I need to be able to access SMTP servers for Wordpress to be able to send emails.

I added an outbound rule to that allows ports 25, 465, 3535 and 587 (GoDaddy SMTP ports) to connect outbound to any IP and to use any internal port numbers.  But, still no love...  (I have not rebooted - is that necc?)

Any ideas as to what I am missing here?  I just know it is something to do with the server security, I just don't know what.
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Mohamed ElManakhlyInfrastructure Team Leader

Commented:
what about telnet port (23)

i believe you need an inbound rule too ..

anyways totally disable your firewall first to make sure it is a firewall issues , if so, do the above.

Author

Commented:
You know....I think I found the problem.  GoDaddy blocks some IPs for spamming.  The IP I got from 1 and 1 hosting for my dedicated server may have been blocked because a previous user was spamming.

I can telnet to other servers without issue.  It's just GoDaddy's servers (smtpout.secureserver.net) that I cannot access.

I am on hold with GoDaddy now...  I will update momentarily...

Author

Commented:
There is no doubt in my mind that the issue is with GoDaddy.

I can install Thunderbird on my local Win7 laptop and connect to the account just fine.  I can connect via Outlook just fine.  I can telnet to every server that I have tired - EXCEPT GoDaddy's servers.

When I was on the phone, the rep said that my server IP was not blocked.  So, I pushed for more assistance.

When he returned to the call the second time, he told me that GoDaddy does not allow relaying email in that fashion.  That's really strange considering that the GoDaddy rep I spoke with yesterday said that they set up an smpt server (relay-hosting.secureserver.net) just for such use and that using that server would allow 1,000 emails a day whereas the normal SMTP server (smtpout.secureserver.net) only allowed 250.

I tried to explain to the rep that the SMTP protocol had not changed significantly for some time, and that the server had no way of knowing if an email client or other application was sending it the data.

He insisted that they could block WP SMTP Mail's attempts at sending email through their SMTP servers.  And, while that may be true (if WP SMTP Mail sends identifying data with it's requests), it still does not explain the fact that I can connect to the email address using Thunderbird or Outlook locally and not be able to contact the GoDaddy SMTP server using Thunderbird from my server.

OK...maybe the server has some IPSec or Firewall settings that are blocking SMTP protocols.  But, that would mean that I could not connect to Gmail or telnet to other SMTP servers from my server either and that is not the case.

I am not Windows Server expert, but it seems to me that GoDaddy is screwing this up and doesn't want the responsibility for it.

If you have any other possible explanations for this, I would love to hear them.
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Infrastructure Team Leader
Commented:
as long as you can login to other Mail servers , you are difinitley blocked by them

Author

Commented:
GoDaddy was on the phone with me for over 3 hours, searching for a solution.  They insist that the IP is not blocked.

1and1 insist that it is GoDaddy's problem and were in a rush to get off the phone after 5 minutes.

When I asked 1and1's rep what would happen if I changed the DNS settings from their DNS server (just in case that is the issue) and turned off DHCP what bad stuff could happen, he said I could lose connectivity to the server and sould have to use a Putty client to go in via the serial port to get to a command line and try and restore DHCP and the DNS settings.

Do I SOUND like I knwo how to do that?  I don;t even know how to fix this issue.

When I asked if 1and1 could change the server's IP address (in case the IP really is blacklisted by GoDaddy's email provider), the 1and1 rep said they could not do that.  But, when I asked if I could BUY another IP and just tirn this one off, he said sue - for 99 cents a month.  Now, what is the difference (besides the $1 a month)?

When I asked what would happen should I not be able to get the server back up - what were my options - he said the only option would be to REIMAGE THE SERVER!  1and1 offered no paid support or paid maintenance assistance.

Steer clear of 1and1 dedicated servers if you think you may need any type of assistance from them.

When I find the solution I will post it here (hopefully soon).

Author

Commented:
Sorry for all of the typos above - 4 hours sleep in 2 days and getting sick....

Author

Commented:
For the time being I am using a Gmail account to get around the SMTP issue.  Here's how....

Start a new Gmail account.

In Gmails Account Settings, turn on the POP capability as shown here...

 gmail pop
Then, set the WP-SMTP-Mail settings as follows (using your own gmail account email and password of course...

 wp smtp settings
As soon as I find out which company is screwing my SMTP abilities up (I'll know within a week), I'll update this thread.

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