Mail Loop End to End check of email

General
1

Hello Team,
I am trying to make use of the plugin “check_mail_loop” whose purpose is to send out eMails to a defined mail address using the SMTP protocol and then tries to receive these mails back by querying the inbox of a IMAP or POP3 mailbox.
The first message gets delivered to the destination email address. However after that nothing happens, the output of the plugin reads " UNKNOWN - Failed to check for mails: [Errno 101] Network is unreachable".
Any ideas as to what could be the problem?.

Thanks

2

My configuration is as follows:
SMTP server: My company’s smtp server for sending out mails.
Mail Receiving:
IMAP server: outlook.office365.com (My comany uses 0ffice365 as local exchange server)
Authnetication : My company email and password
From: email address : My company email
Destination email address : A gmail account which I created and configured auto response on it.

3

If your destination address is a Gmail address then you need to put in the Google IMAP server instead of the Office365 IMAP server.

The SMTP server info is used by the check to send the email.

The IMAP server info is used by the check to receive the email that was just sent.

The check sends a unique token within the email to identify its messages. An autoresponder will not work.

4

Thanks for your feedback. I appreciate.
The goal is to ensure we are getting external emails.
Since the auto responder will not work, what would you suggest.
Also will using my My company email and password as the authentication be correct. Since the IMAP server would not be outlook.office365.com.
Thanks in anticipation of your response.

5

If you want to check if you can receive emails from external senders you need to put the credentials of your test gmail account into the SMTP section of that configuration.

The destination email address then is your company email address.

Then the email is sent from gmail to your company account.

6

Thanks for the feedback.
I will try this out once I get back to office.

7

I already tried it and also gave all Firewall access. Now check_mk can send from the gmail account to my internal office mail. But I am now getting the error “UNKNOWN - Failed to check for mails: timed out”
At first it was “UNKNOWN - Failed to check for mails: Bad login”.

Note: the Imap server is the company’s Imap server and my company email address and password as the authentication.
I have tried with and without ssl encryption. Also used “Use TLS for IMAP authentification”

Any ideas please.
Thanks

8

Now using just “Use TLS for IMAP authentification”” and getting
UNKNOWN - Failed to check for mails: LOGIN failed.

9

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