Setting up SMTP under IIS 7 on Windows Server 2008 - iis

Question

Website started life originally under IIS 6 and the site worked great there. Now after relocating to a new server running W2K8S, everything but mail delivery from the website now works great under IIS 7.
Researched briefly on the Web to see if anybody had a good resolution, but no avail... Not even a glimmer of hope on Microsoft's own support site.
Here are the steps taken so far on the new W2K8S box:
Added the feature for SMTP under the Server Manager
Enabled SMTP e-mail for the site itself in IIS 7 Manager to deliver e-mail to SMTP server local host, unsuccessful
Enabled SMTP e-mail for the root site in IIS 7 Manager (not sure if that needs to be on to enable sites) to deliver e-mail to SMTP server local host, unsuccessful
After failing those basic setups, I wanted to be sure I can actually talk from/to the serveron port 25. And I can successfully telnet from/to the server in question to a test e-mail on port 25 get a HELO, etc. So I do not believe it is a firewall config issue.
The IIS 7 setup test was performed with both anonymous and Windows authentication - no luck either way.
Manually checked Web Config file and it reflects correct entry for the server to use the localhost.
Read the manual and no luck there either... :-/

Answer 1

I faced the same problem.
I came across this link http://www.frontpagewebmaster.com/m-215289/tm.htm
and I was able to solve the issue. Go to the last post of this link.
In my case I solve problem by giving rights to "NETWORK SERVICE" user to the "Pickup" folder.
Hope this might help....

Answer 2

OK, to the post that said "give NETWORK USER the write rights to the pickup folder" it finally works. What I did was:
You need to use a "smart host" unless you are running exchange server. I am using a Gmail account, Gmail allows SMTP forwarding.
You can use Windows authentication for security on the SMTP server and the IIS7 config setting.
First step, set the delivery method = "network" in your web page, and get your smart host configured independently of the SMTP server.
SmtpClient client = new SmtpClient("smtp.gmail.com", 587);
client.DeliveryMethod = SmtpDeliveryMethod.Network;
client.UseDefaultCredentials = false; // use your smart host login client.Credentials = new NetworkCredential("xxxxx#gmail.com", "password");
client.EnableSsl = true;
This will send the email directly and bypass your SMTP server.
Second step, once you have that working, write a sample windows app to use your SMTP server independent of your web page, and get that working.
SmtpClient client = new SmtpClient("your server ip", 25);
client.DeliveryMethod = SmtpDeliveryMethod.PickupDirectoryFromIis;
client.EnableSsl = false; // you can't use ssl with a pickup folder
client.UseDefaultCredentials = true; // use windows credentials
This will bypass your web page and make sure you have your SMTP server configured properly.
Finally, get your web page working, by setting the sharing on your pickup folder to allow write access to NETWORK_SERVICE. Transfer the login info from step 3, into your SMTP settings, set authentication to integrated security, and use the code in step 4 for your web page.

Answer 3

I had exactly the same problem as described in this old question. Finally I found a solution to it. In my case the operation system is W2008 R2 with IIS 7.5, but I think this doesn’t matter.
The underlying problem is that the SMTP Service in W2008 R2 seems to be a legacy part of the IIS. It is installed with the IIS 6.0 administration tools, side by side to the IIS 7.X Server. This causes two derived problems:
IIS 7.X knows nothing about the SMTP service. If you configure SMTP in ASP.NET to use the PickupDirectoryFromIis this results in an exception. Therefore you can’t use this SMTP configuration:
<smtp deliveryMethod="PickupDirectoryFromIis" />
But it is possible to configure SMTP with SpecifiedPickupDirectory, You can use this configuration:
<smtp deliveryMethod="SpecifiedPickupDirectory">
<specifiedPickupDirectory pickupDirectoryLocation="C:\inetpub\mailroot\Pickup" />
</smtp>
If you configure the pickup directory in this way, you may run into a second kind of problem: IIS6 and IIS7.X have different security systems. IIS 7.X introduces integrated security with application pool identities. IIS 6.0 and its SMTP service don’t know about this. Therefore you have to grant write permissions for IIS_IUSRS to the pickup folder. In my configuration the pickup folder is C:\inetpub\mailroot\pickup.

Answer 4

I noticed that the event ID 4006 was refering to the domain controller ip instead of the mail server ip.
I used the iis 6 admin tool to configure a smarthost pointing to the mail server and voila! the issue was resolved.

Answer 5

I am not sure if this diagnostic tool can provide more insights,
http://www.iis.net/downloads/default.aspx?tabid=34&g=6&i=1308
This tool is for x86.

Answer 6

Have you checked to see if the SMTP service is accepting mail for relay from localhost? To do this, telnet from the machine in question to the local SMTP server and use SMTP commands to send a test message. The SMTP service is very picky about command formatting so you'll have to be careful when entering commands (i.e. don't use backspace to correct typographical errors).

Answer 7

Is this, by chance, an old "classic" ASP app relying on CDONTS to send mail?
If so, perhaps one of these links would be helpful?
Edited: I had replied before noticing the note on the original post. Disregard...

Answer 8

I came across this post when researching getting SMTP running on my ASP.Net app we're migrating from IIS6 to IIS7. What I found was we didn't have to set up the SMTP SERVER at all - simply setting up SMTP Email was enough - with the additional benefit of NOT having the security concerns of SMTP relaying thru the web server!
so if you don't need your web server to actually do the SMTP routing, you don't have to set up the server at all in IIS7.