How to Install Smtp Server in Windows Server 2008 R2
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I have been wrestling with setting up SMTP on a Windows Server 2008 R2 for weeks now. We have an application (Pearson PowerSchool) which needs to send email (not receive it). We do not use Exchange. Our main web site and domain are hosted by HostGator. Our Internet connection is through Comcast. We do not have a static IP address but use No-IP.com for dynamicDNS.
I have installed IIS7 on port 8080 (PowerSchool uses port 80). I want to use GMail since we use GMail for our email service. I bring up SMTP on the server, use port 587, smtp.gmail.com as the smart host, but I cannot send email. The server is Moxie.hhne.local. I have used that as the domain name, hhne.org as the domain name, and myhhne.org (external access to PowerSchool) as the domain name but still nothing. Our certificate provider does not think that I can do what I am trying to accomplish since our main domain is hosted elsewhere.
Can anyone offer me some guidance or point me in another direction? I have run out of ideas. I appreciate your help and assistance.
Fred Zarnowski
HHNE
zarnowski@hhne.org
ProfessorFZ wrote:
Hi Scott and thanks for your reply. I really don't know what setting my server up as a sendmail server means. I'll google around for some ideas. I have used the W2K8R2 resource kit and documentation and also googled around for setting up an smtp server. Maybe I am trying to do too much. I have a student information system (Pearson's PowerSchool) which wants to send emails to a parent when say a teacher posts a grade for a student. So it is a one-way arrangement. It seems like it should be simple but sometimes the simple things turn very complicated.
If you don't have any luck, try this:
Under your SMTP Virtual Server Properties
-Access Tab, Authentication -- check Anonymous access
Still under the Access Tab, Relay -- Choose one of the options for whom to allow.
If you choose Only the list below, pick an IP of a PC that you know, and set their outgoing server (SMTP) in their email client to the IP of your server and send a test email to yourself or someone nearby. If you know the server name, you can also use that instead of the IP adress. They'll also have to remove the authentication settings and set them back to defaults for SMTP or outgoing. If you have someone who has a standard setup already, this will be easier. Use port 25 (which should be the default) for their outgoing server, leave the pop or incoming settings alone. Remember, you're only trying to change your outgoing behavior.
You should get a successful transmission. If you are only using this for an App to send mail from one machine, you can further lock it down by only allowing the IP address of the sending PC on which the App resides. I do this for our copiers to scan to email and it works fine. One way only.
If you've never hosted your own email services, you should keep in mind that this is a very relaxed setup to host your own sendmail service. If you get this working, you should at least consider having users use their domain account logins. As always, you can tighten this up more, but it should get you going.
Good Luck
PS I should clarify that when I say sendmail, I'm definitely using the term wrong. Sendmail is a program for sending mail that has been on the 'NIX' variants for many many years and shouldn't be confused with the SMTP service on a Windows Server. I'm sure the gurus are positioning themselves for a lynching right now. What I just did is kinda like swearing :)
10 Replies
Hi,
When ever I try to troubleshoot mail issues I generally start on the command line.
On the server running the smtp locally I suggest you try to
>telnet localhost 25
and see if you can see mail system headers etc
you can google "checking mail manually using telnet" to see the other commands you can use
then try and send mail from the addresses you have specified in the application to an example address that you intend it to go to.
hopefully the feedback you get from running these kind of commands will help tie the problem down.
Have you configured the SMTP virtual server at all?
Yes, I configured SMTP virtual server. Apparently you still need the IIS 6.0 Manager to do so. I set the smart host as smtp.gmail.com, se for basic authentication and entered our gmail username and password for the application, set the port to 587, and made sure that all IP addresses have access.
Mail that goes into the pcikup folder gets moved to the queue folder but goes no further. I have checked our SonicWall firewall and port 587 is open.
IIS has logs the location of which can be found in the properties of the SMTP virtual server. Have you checked it for errors yet?
This is one of the messages in my log file:
Message delivery to the host '74.125.91.109' failed while delivering to the remote domain 'zarnowski.us' for the following reason: The remote SMTP service rejected AUTH negotiation.
The SMTP verb which caused the error is 'AUTH'. The response from the remote server is '250-mx.google.com at your service, [71.235.243.35]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
And this:
No usable TLS server certificate for SMTP virtual server instance '1' could be found. TLS will be disabled for this virtual-server.
Have you tried to use your SMTP server as just a sendmail only server without a smarthost? In other words, send an email with only the destination and don't try to authenticate using your normal smtp server. Forgive me, but it sounds as if your attempting to setup your server more as a relay server than as a sendmail server/service.
If I'm right, you should be able to set allow anonymous in your permissions and you can tweak it down to the IP address of your senders or to allow all for the addresses to test it out. Once you get a successful send, you can tighten it up. For your test, set your server up as your smtp server.
Good Luck.
Hi Scott and thanks for your reply. I really don't know what setting my server up as a sendmail server means. I'll google around for some ideas. I have used the W2K8R2 resource kit and documentation and also googled around for setting up an smtp server. Maybe I am trying to do too much. I have a student information system (Pearson's PowerSchool) which wants to send emails to a parent when say a teacher posts a grade for a student. So it is a one-way arrangement. It seems like it should be simple but sometimes the simple things turn very complicated.
ProfessorFZ wrote:
Hi Scott and thanks for your reply. I really don't know what setting my server up as a sendmail server means. I'll google around for some ideas. I have used the W2K8R2 resource kit and documentation and also googled around for setting up an smtp server. Maybe I am trying to do too much. I have a student information system (Pearson's PowerSchool) which wants to send emails to a parent when say a teacher posts a grade for a student. So it is a one-way arrangement. It seems like it should be simple but sometimes the simple things turn very complicated.
If you don't have any luck, try this:
Under your SMTP Virtual Server Properties
-Access Tab, Authentication -- check Anonymous access
Still under the Access Tab, Relay -- Choose one of the options for whom to allow.
If you choose Only the list below, pick an IP of a PC that you know, and set their outgoing server (SMTP) in their email client to the IP of your server and send a test email to yourself or someone nearby. If you know the server name, you can also use that instead of the IP adress. They'll also have to remove the authentication settings and set them back to defaults for SMTP or outgoing. If you have someone who has a standard setup already, this will be easier. Use port 25 (which should be the default) for their outgoing server, leave the pop or incoming settings alone. Remember, you're only trying to change your outgoing behavior.
You should get a successful transmission. If you are only using this for an App to send mail from one machine, you can further lock it down by only allowing the IP address of the sending PC on which the App resides. I do this for our copiers to scan to email and it works fine. One way only.
If you've never hosted your own email services, you should keep in mind that this is a very relaxed setup to host your own sendmail service. If you get this working, you should at least consider having users use their domain account logins. As always, you can tighten this up more, but it should get you going.
Good Luck
PS I should clarify that when I say sendmail, I'm definitely using the term wrong. Sendmail is a program for sending mail that has been on the 'NIX' variants for many many years and shouldn't be confused with the SMTP service on a Windows Server. I'm sure the gurus are positioning themselves for a lynching right now. What I just did is kinda like swearing :)
Hi Scott, The application itself is located right on the server. Still can't get it going. Thanks for your reply.
I was able to get this going but Spiceworks was not letting me post to this thread for some reason. It came down to constant fiddling with the settings in the SonicWall firewall, the PowerSchool application, and W2K8R2. Eventually, I hit on the right combination and we are able to send from the PowerSchool application through the Gmail SMTP Server. Thanks for all for your replies.
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How to Install Smtp Server in Windows Server 2008 R2
Source: https://community.spiceworks.com/topic/160989-smtp-on-windows-server-2008-r2