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1. Setup → Services → HTTP, TCP, Email, ... → Check Email Delivery → Add Rule
   
   
   • Name: The service description will be Mail Loop plus this name
   • Subject: Here, you can specify the subject text instead of the default text 'Check_MK-Mail-Loop'.
   • SMTP Server: You can specify a hostname or IP address different from the IP address of the host this check will be assigned to.
   • Use TLS over SMTP: Encrypt SMTP communication using TLS
   • Use TLS for IMAP authentication: IMAP authentification authentication uses TLS
     
   • SMTP TCP Port to connect to: The TCP Port the SMTP server is listening on. Defaulting to 25.
     

   • SMTP Authentication:  Your credentials for the SMTP Server
     
     
     

     
     

   • Mail Receiving
     • IMAP/POP3: Chose whether you want to use IMAP or POP3
       
     • IMAP Server: You can specify a hostname or IP address different from the IP address of the host this check will be assigned to.
       
     • SSL Encryption: Encrypt IMAP communication using TLS
       
     • Authentication: Your credentials for the IMAP Server
       
   • From: email address

   • Destination: email address

   • Connect Timeout: Timeout in seconds for network connects (defaults to 10)
   • Loop duration: Loop duration of the most recent mail in seconds or the average of all received emails within a single check to raise a WARNING/CRITICAL state

   • Delete processed messages: Delete all messages identified as being related to this check plugin. This is disabled by default, which might make your mailbox grow when you do not clean it up manually.
     
     

     
     

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Execute active Check manually

or For debugging reasons, it could be helpful to run the check manually. Therefore, you need to open the service site of the E-Mail service and search for 'Service check command'. Now you can use the command for executing the check manually.
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OMD[mysite]:~/lib/nagios/plugins$ ./check_mail_loop--pwstore=4@16@provider1,10@17@provider2 '--smtp-server=smtp.provider1.com' '--smtp-tls' '--smtp-username=user@provider1.com' '--smtp-password=*************' '--fetch-protocol=IMAP' '--fetch-server=imap.provider2.com' '--fetch-ssl' '--fetch-port=993' '--fetch-username=mail@provider2.com' '--fetch-password=*************' '--mail-from=user@provider1.com' '--mail-to=mail@provider2.com' '--delete-messages' '--status-suffix=localhost-Email Delivery' '--warning=120' '--critical=300' '--subject=Check_MK-Mail-Loop for Strato'

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tag login <username> <password>

You can also use nmap for further debugging:

root@mylinuxhost:~# nmap smtp.server.tld

This command will show open ports, which will help us to identify which port we need to use in Checkmk:

Starting Nmap 7.80 ( https://nmap.org ) at 2024-12-24 12:44 CET
Nmap scan report for smtp.strato.de (81.169.145.133)
Host is up (0.029s latency).
Other addresses for smtp.strato.de (not scanned): 2a01:238:20a:202:55f0::1133
Not shown: 994 closed ports
PORT STATE SERVICE
135/tcp filtered msrpc
139/tcp filtered netbios-ssn
443/tcp open https
445/tcp filtered microsoft-ds
465/tcp open smtps
587/tcp open submission

More information can be found one Nmap's official site.

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