New Install, Windows Agent not connecting

Latest version of CheckMK. Create MSI file for windows 2019 server. Install went fine. Back on server, Add server under hosts. Run communication test. Ping works, Agent reports Communication Failed: timed out.

Tested adding both a firewall run on the 2019 server for both 6556 in and out. Did not fix it.
Tested turning off firewall on 2019 server - Did not fix it.
Reinstalled agent - still no solution.

Unsure why I cannot get the windows agent to talk back to my server. Server is Ubuntu 22.04

When you run uninstall/reinstall, agent registration is mandatory:

I’m a little confused. This windows machine never had checkmk on it until I installed it for the first time. On the server side, I would delete the host entry and add it again and run the communication test again after each test of the client. I tested doing an install on one of my other Linux machines as a client and it communicated back just fine. For some reason, windows does not let me pass the agent test if its a windows machine talking to a server which is Ubuntu.

Believe me: There are rare cases whre the new Agent Controller does not run in legacy mode after installation, here you have to run the registration immediately after adding the host for successful connection tests and service discovery.

After I run the MSI files I copied over to the Windows 2019 server, I executed it and then switched to the Checkmk server and added the host within the same minute that the wizard ended and only ping works. The agent test still times out. I adjusted this timeout and it did not effect it.

What is legacy mode? I thought that would be for older machines or older installs of checkmk. This is a new install with the latest version and the client is a Windows 2019 OS. Is that considered old?

With legacy mode we mean the unencrypted communication on port 6556. This should be available after a fresh install but unfortunately isn’t always. In this case it’s necessary to do Agent Controller registration before service discovery is possible.

Sorry if this is a silly question. What is Agent Controller registration? Is it when I add the client under host and add the server name and IP and check the checkbox for Monitoring Agent?

Read the link I posted above. You might scroll up for the introduction:

After a lot of troubleshooting I found this solution that worked for registering.

But what is odd now is that in the communication test the agent works but ping fails. Because ping is failing, it tells me the host is down. If I start and stop my network on my server, pings works again but agent again fails. When agent was working, service discovery worked. Just now have to figure out why ping fails.

mschlenker - your link pointed me in the right direction but my concern is if I have to register everyone of my windows hosts this way. I sure hope not. I watched a lot of tutorials on installing checkmk on windows clients and none of them had this kind of issue. I was hoping the deployment of these agent would not required so much backend work on each host.

This is the new way in Checkmk 2.1

I am also concerned that there seem to be situations where the new agent does not start in “legacy” mode any more. This looks like a new feature with much manual work is forced upon the user.

Not sure if this helps you but when I have ping issues its normally because ping is turned off in firewall settings. Its the ICMP ones for the network type your host is using. Once enabled, ping should work.

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