How to fix RDP connection stuck at "configuring remote session" or offline machine

If a user is trying to connect to a remote machine and their RDP connection gets stuck as "Configuring remote session", this is because the endpoint is not accessible from the TruGrid Sentry or TruGrid Secure Connect agent installed.


How to fix this as an end user
If you're an end user trying to connect to a machine at your office, please ask someone at your office to check if the machine is turned on and accessible and responding. If it is turned on, restart it in case it is hung. If it is not turned on make sure to turn it on, otherwise, you won't be able to connect to it via TruGrid. If this does not fix it, please provide the below information to your administrator.

Troubleshooting Steps For Administrators
If you are an administrator of the machine at the office and know the machine is online and not hung, below are some additional troubleshooting steps. These are things we cannot remediate for you and need your help with. Generally the root cause is DNS is not resolving to the current IP address or RDP is not accessible from the server the TruGrid agent is installed onto.

Most Likely Root Causes
Reboot Endpoint and Remote Computer A reboot fixes lots of issues in Windows. Sometimes, a pending update requiring a reboot will block the computer from functioning properly. Please reboot both the Endpoint computer that user is connecting from and the remote computer that user is connecting to. If user still cannot connect thereafter, please follow the rest of this article.
Install Latest Desktop Connector Ensure you have the latest Desktop Connector application installed. Uninstall the currently installed one and then install the latest version.
Accurate Internal DNS Resolution (for more detailed troubleshooting steps please see THIS GUIDE) Ensure the IP address internal DNS is returning is the current accurate IP address for the machine. Make sure to check from the server the TruGrid Sentry agent is installed onto. You can do this by going to a Command Prompt and typing "nslookup {hosthame}" and see what IP address it returns. If the incorrect IP address is showing, then TruGrid will not be able to broker the RDP connection properly. To remediate an incorrect IP address, check the internal DNS console for any DNS records (forward and reverse) related to that machine hostname and IP address. You might also want to ensure the machine has a static or reserved IP address. If you have to correct an IP for a machine, we recommend you then remove it from the TG-Computers group, restart the local TruGrid Sentry service and then add it back to the TG-Computers group. We have also seen certain situations where an IPv6 configuration could cause issues with how the machine registers into local DNS and causes DNS resolution to the IPv4 address to fail. To troubleshoot this and isolate if this might be the issue, you could try to delete the incorrect adapter registering the IPv6 address, so that the proper IPv4 address could register. Here is a YouTube video someone put together showing those steps.
RDP from Server: If the endpoint is an AD-joined machine, log into the server the TruGrid Sentry agent is installed onto and try to RDP to the machine they are trying to connect TO. Please don't assume because you can connect to it from another machine on the network that it is accessible from this server.

Other Possible Root Causes
Accurate Date/Time: Ensure the clock date and time are accurate on the machine being connected FROM and the machine, the machine being connect TO, and the server the TruGrid Sentry agent is installed onto. If the time is off it can impact encryption keys and cause connection failures.
RDP Port Open: Make sure the Windows OS firewall on the machine being connected TO is open for RDP port 3389.
RDP Enabled: Ensure RDP Remote Access is enabled on the endpoint
Routing Issue: Are there multiple network adaptors on the machine that could be causing routing issues? Try to disable one and see if it helps.
Machine Awake: Ensure endpoint is set to not go into sleep mode and is awake and responding.
Correct Network Configuration: Ensure the machine has accurate local network settings and is pointing to the same local DNS server that the TruGrid Sentry agent server is pointing to. Check also on the TruGrid Sentry server to make sure it is pointing only to a local DNS server.
Allows Outbound Traffic: Check if there are any outbound firewall restrictions. See further instructions here.
Check Sentry Local Log Files: Check the local log files of the TruGrid Sentry agent on the server installed onto, and see if any log files point to issues connecting to this machine. These log files can be found at c:\program files\trugrid\sentry\agent.log.

If none of the above items help resolve the problem, you could try installing the TruGrid Secure Connect agent onto that machine to see if this works and helps isolate the problem further.
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