IIS7 SMTP Server sends email after long time - email

I have a Windows Server 8 machine with IIS7.
I have configured a SMTP server on IIS7, to be used by a .NET Web Application sending some notifications to the users of a system.
The SMTP server is configured to Deliver emails to SMTP server, on port 25, using localhost, no authentication.
My problem is that the emails are sent correctly, but not until after a day or even longer. I see the emails in the pick-up directory from wwwroot, but they just stay there. For the system it is quite important that the emails are sent immediately.
How can I ensure the emails are sent imediatelly?
I found a question which addressed a similar problem (in that case the emails didn't came off pick-up directory, in my case they are send after a day or so) Need help setup windows server 2008 SMTP server But the answer given is quite incomplete so I could not check if it will also solve my problem.
This is the code I use:
MailMessage mailMessage = new MailMessage();
mailMessage.To.Add(toEmail);
mailMessage.From = new MailAddress(fromEmail);
mailMessage.Subject = emailSubject;
mailMessage.Body = emailBody;
mailMessage.IsBodyHtml = true;
SmtpClient smtpClient = new SmtpClient();
smtpClient.DeliveryMethod = SmtpDeliveryMethod.PickupDirectoryFromIis;
smtpClient.Send(mailMessage);

Can you post your code that sends the emails, or at least confirm that it's not overriding the IIS settings? Are different SMTP properties set at different levels - possibly at the server and at the website?
You can try something like this, which should allow the emails to be sent immediately by the SMTP service instead of being stored in the pickup directory:
var smtpClient =
new SmtpClient("127.0.0.1", 25)
{
UseDefaultCredentials = false
};

Related

Local email to root should not leave the host

I am trying to set up the most simple email server on an Amazon Linux 2 host for simple outbound mail (e.g. sending system messages). Following instructions on the net, I have installed mailx and sendmail. I am not committed to either package, I just want a simple setup with a minimal footprint. I have no problem switching to postfix if that is a better solution.
For configuration I have made the following changes.
/etc/sysconfig/sendmail:
DAEMON=no
/etc/mail/submit.cf (hostname obfuscated):
D{MTAHost}smtp.******.com
This works fine, and I am able to receive mail that is sent from the system.
There is a wrinkle. The anacron process is sending mail to the root account. However, rather than the mail being kept internal to the system it is being sent to the SMTP server. The SMTP server sends the message back to my host, which doesn't accept mail, and a loop is created when an 'undeliverable' message is send back to root on the host that doesn't accept mail.
How can I configure my system so email to root stays local and is not sent to the SMTP server? Any other 'best practices' suggestions would be welcome as well. And again, if switching to postfix is better, I am willing to do so (but will need configuration guidance).

How to setup minimal smtp server on localhost to send messages to other smtp servers

Honestly, I think I have a fundamental gap in understanding how SMTP works. I can't seem to find a good explanation of what is happening behind the scenes and I think this is preventing me from being able to do what I am attempting to do.
To explain, I'm trying to setup an application which sends notifications to users by connecting to an SMTP server. Fair enough. I figure, since I'm using my own domain, I have SPF/DKIM/DMARC configured, I can add an MX record for the host I set the application up on (my SPF record has the mx keyword to authorize any hosts in my MX records to send/receive mails). Then, I can have that same host run a super lightweight SMTP server that can accept mails from the application, and send them on to recipients.
Almost crucially, I want this server to basically just run on localhost so that only this application can connect and send mails through it, but so that it can't really "receive" mails sent to my domain (I have set the MX priority very low (well, a high number) for this app server). I figure since I'm running my own SMTP server, that I don't really need to authenticate against it (it's running on localhost), just take in any mail and send it on to recipient domains.
When sending on to recipient domains... does the SMTP server need to authenticate to say, the gmail SMTP server as a user in order to send mails over there? That seems weird, since it's not a user logging into gmail to send mails, it's an SMTP server that is authorized within SPF sending mail from my domain (From address from my domain as well) to where ever the app server user's email is based (in this example, the user would be e.g., some_user#gmail.com).
I tried using python's aiosmtpd command-line and telnet to send a mail from test#MY_DOMAIN.TLD to test#MY_DOMAIN.TLD and it didn't seem to deliver the message; I figured aiosmtpd would connect to the preferred MX servers for my domain (my "real" MX's) to transfer the message, which would then put it in my inbox. That didn't seem to be the case, and I'm not sure why.
Exact repro steps, where example.com is my domain, and terminals are running on a box with a hostname listed in my MX records.
Terminal A:
$ aiosmtpd -n
Terminal B:
$ telnet localhost 8025
EHLO <example.com>
MAIL FROM: test#example.com
RCPT TO: test#example.com
DATA
FROM: Application Notifications <test#example.com>
TO: User Name <test#example.com>
SUBJECT: App Notify Test
This is a test!
.
QUIT
How do SMTP servers normally send mail between each other? Do they each get some login to each other's SMTP servers to authenticate with, and since I'm not doing that, this is a problem? Can I run a SMTP server on localhost and have it send mail out of the network without receiving mails (a no-reply service)? Is there something obvious that I'm just missing here that solves all my problems?
Thanks
It sounds like you want to run a mail transfer agent (MTA) that relays email to remote SMTP servers. An MTA will typically act as an SMTP server to receive messages, and then it will act as an SMTP client when it relays the messages to remote hosts.
MTAs generally operate in two different modes: (1) They will relay messages from authenticated users to remote hosts, and (2) they will receive messages from remote hosts to its users and store them somehow. The combination of those two modes - where the MTA will accept messages from remote hosts and relay them to different remote hosts - is called an open relay and is sure to attract spammers and place your server on spam blacklists.
aiosmtpd is not an MTA or an email relay out of the box - it is merely an SMTP server that will receive messages and do whatever with the messages you program it to do. By default it will do nothing - that is, it will receive the messages and throw them away. If you want to implement an email relay in aiosmtpd, then you need to implement the SMTP client portion of the MTA, e.g. by implementing an aiosmtpd handler that instantiates smtplib.SMTP to connect to remote hosts.
However, if all you want is an email relay, then you most likely don't need aiosmtpd at all - postfix is probably a better choice.
aiosmtpd can be a good choice if you need to implement mailing list software or perform some automation tasks based on incoming emails from e.g. cameras or scanners.
If you want to implement an email relay in aiosmtpd, then you need to ensure that both the software and your server are configured in a way that you don't relay unauthenticated messages from the outside internet.
See also: Python aiosmtpd - what is missing for an Mail-Transfer-Agent (MTA)?
So, I actually figured out what was missing here.
I need to run an SMTP server, yes, but I also needed to write code to parse the "to" domain (the recipient domain), perform a DNS request for the MX server(s) of the recipient domain, and then use the smtplib client to then send mail over to the recipient domain. Authentication is not needed to relay that message to the recipient server, authentication is only required for reading from a given inbox or authenticating a sender to send on behalf of a domain (I trust myself and myself only to send mail). I can do all this while also only listening for mail on localhost so that only my local server can use the local SMTP server for relaying messages/emails off to recipient domains.
Additionally, I don't need to have my external IP listed as an MX server since it's not accepting mail for the domain, only sending. I do need an SPF record for it though so that it is an authorized relay/sender for email from my domain.

cPanel email routing... if not found locally try remote

I've got a weird setup with my emails that I need someones brain to look at. I've got it setup like this so that most of my emails are on one server (server1) and then 1 single account is setup on a second server hidden from the rest (server2)
Email Sent to user1#domain.me
MX record for domain.me = mail.domain.me
A record for mail.domain.me = server1 (11.11.11.11)
Email forwarding rule forwards all email sent to user1#domain.me to user#2.domain.me
MX record for 2.domain.me = mail2.domain.me
A record for mail2.domain.me = server2 (22.22.22.22) a cpanel server
Email hits my server now addressed to user1#2.domain.me
Domain forwarding rule forwards all email sent to #2.domain.me to #domain.me
This works great however my mail routing in cpanel is set to local, and therefore when sending emails out on server2 (22.22.22.22) to users#domain.me they're always delivered locally first and foremost
Is there any way around this? so that outgoing mail on this domain obey's DNS records (the mx records) and delivers it firstly to server1 (11.11.11.11) as if it was being sent from any other domain, gmail etc. Perhaps if the account isn't found locally then send on out to the web? Or perhaps there is a way to setup an alias somehow to let the local account receive mail for user1#2.domain.me
Thanks for your time & efforts looking into this
Henry
Check if your remote domains are listed in /etc/remotedomains and /etc/secondarymx. Note that if your second server has a dns server, it will try fetch the dns data locally first.
I have 2 servers using cpanel where each server acts as the other's backup and I don't have the issue you described.

SMTP Mail Failures to a certain domain

Do the SMTP logs on a server (Windows 2003) only show logs of mail that were sent successfully?
We are getting bounce backs when sending mail to a particular domain:
The connection was dropped by the remote host.
It looks like a problem on the receiving server, but we dont have much information to provide them. We can send to hotmail, gmail, yahoo etc OK.
Any ideas?
Most likely, there is a spam filter in front of the receiving mail server for this domain, and this spam filter thinks your mail server is sending spam, so it's closing the connection from your mail server. One way to test this is to simulate sending a message to this mail server by opening a command prompt on your mail server, and use telnet to connect to the receiving mail server on port 25, and proceed with the process of sending a message just as a mail server would. This way, you'll be able to see how the receiving mail server responds after each step. Follow the instructions in http://support.microsoft.com/kb/153119 to see how this is done.
It turned out the sending server was blacklisted by McAfee, that was running on the receiving servers firewall.
For those that may have the problem in the future you can check if your server is blacklisted with McAfee here:
http://www.mcafee.com/threat-intelligence/ip/spam-senders.aspx
After entering your server IP, you should see a link Threat Feedback. Use this to email McAfee.
I was able to send McAfee an email with an explanation, they then removed our server from the blacklist.

Switched exchange servers, kept the same e-mail but some incoming mail is still going to the old server

I recently switched from an axoim exchange mail server to microsoft 365 exchange server. Now my email address is still the exact same as it was, and most of the incoming mail comes to my new server and address, but it looks like some incoming mail is still going to the old server. Why is that and what can i do to address it?
I'm assuming that you changed the MX records for your domain, so that they now point to Microsoft 365's mail servers, correct? If so, it may take a day or two for the DNS changes to propagate.