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Windows Agent | Troubleshooting Agent Installation Error 500

Agent install error 500, Internal Server Error, Agent Error 500

Updated over 3 weeks ago

Overview πŸ’₯

During installation of the Liongard Windows Agent, you may encounter Error 500 (Internal Server Error). This error typically occurs during the agent registration phase, when the installer attempts to communicate with Liongard’s API.

While the error message references a server-side failure, this issue is most commonly caused by local endpoint conditions that prevent successful registration or secure communication.


What Does Error 500 Mean in This Context? πŸ€”

An example error message may look like:

System.Net.WebException: The remote server returned an error: (500) Internal Server Error. 
at System.Net.HttpWebRequest.GetResponse()
at LiongardAgentShared.Services.API.ApiClient.GetResponse(HttpWebRequest request)
at LiongardAgentShared.Services.API.ApiClient.RegisterNewAgent(AgentRegistrationRequest agentRegistrationRequest)
CustomAction RegisterAgent returned actual error code 1603 (note this may not be 100% accurate if translation happened inside sandbox)

Key takeaway:

This does NOT usually indicate an outage or failure on Liongard’s servers.
It typically indicates that the agent could not successfully register due to local system, configuration, or security controls.


Common Causes πŸ€’

Error 500 during agent installation is often associated with one or more of the following:

  • Firewall, proxy, or SSL inspection blocking outbound HTTPS traffic

  • Antivirus or EDR interfering with MSI custom actions

  • TLS or certificate validation issues on the endpoint

  • Duplicate or conflicting MachineGuid / Device GUID

  • Previously failed or partial agent installations

  • Environment name mismatch during registration

  • Endpoint unable to reach Liongard API endpoints during install


Recommended Troubleshooting Steps (In Order) πŸ§‘β€πŸ«

1️⃣ Connect to the Host Device

Ensure you are logged into the exact Windows device where the Liongard Agent needs to be installed.

2️⃣ Download a Known Working Agent Version

Download Agent version 4.2.4 using the provided link:

‼️ This version is known to install successfully in scenarios where newer installers initially fail to register.

3️⃣ Install the Agent

Run the installer and proceed through the standard installation process.

  • Do not specify a custom service account

  • Allow the agent to install using the default SYSTEM context

4️⃣ Verify Installation

After installation completes:

  • Open Control Panel β†’ Programs & Features

  • Confirm Liongard Agent appears in the installed applications list

5️⃣ Manually Trigger the Agent Update

  1. Open Task Scheduler

  2. Navigate to the Liongard folder

  3. Locate the Liongard Agent Updater task

  4. Click and select Run

6️⃣ Confirm the Agent Version

Once the update task completes:

  • Recheck Programs & Features

  • Confirm the agent has updated to the latest available version

βœ… If the agent updates successfully, no further action is required.


If the above Steps Do NOT Resolve the Issue 🧐

If Error 500 persists or the agent fails to register or update after completing the steps above, proceed with the advanced troubleshooting steps below.

Use the Liongard Agent Install Script

If the MSI installation or manual update fails, Liongard strongly recommends using the Agent Install Script, which handles edge cases the MSI alone cannot.

Why This Script Works Better

The script adds safeguards and diagnostics, including:

Capability

What It Solves

Silent MSI execution

Avoids UI-based MSI failures

Configuration validation

Prevents invalid URL, key, or environment values

Environment name matching

Ensures correct environment assignment

MachineGuid collision detection

Prevents duplicate or overwritten agents

Optional uninstall before install

Cleans up failed or partial installs

Backend record cleanup (scored)

Removes orphaned agents only when safe

Full transcript logging

Captures decision logic and failures

MSI installer logging

Provides clear install exit codes


Logs to Collect After Running the Script πŸ‘¨β€πŸ’»

After running the script, if failure persist collect both logs:

Script Transcript & Diagnostics

C:\Liongard\LGAgentScript_<timestamp>.log

MSI Installer Log

C:\Liongard\AgentInstall.log

πŸ“Œ These logs are critical for identifying registration, network, or identity-related failures.


After Installation: Validation Checklist πŸ—’οΈ

Once installation completes:

  • Confirm LiongardAgentSVC is running

  • Verify the agent appears in Admin β†’ Agents

  • Confirm heartbeat status is Online

  • Ensure the agent is assigned to the correct Environment

  • Allow at least one inspection cycle to complete


FAQ's πŸ™‹β€β™‚οΈ

Q: Does Error 500 mean Liongard is down?

No. In nearly all cases, Error 500 during installation is caused by endpoint-side restrictions or configuration issues.

Q: Can antivirus or EDR cause this error?

Yes. MSI custom actions, outbound HTTPS calls, or service creation can be blocked, resulting in registration failure.

Q: Should I keep retrying the MSI?

No. If the MSI fails once with Error 500, move directly to the Agent Install Script to avoid partial installs.

Q: Will reinstalling overwrite an existing agent?

The script explicitly checks for MachineGuid collisions and only overrides when necessary, preventing unintended overwrites.


When to Contact Support 🦁

If the issue persists after using the Agent Install Script, contact Liongard Support.

Please include the following with your ticket:

  • Screenshot or exact text of the Error 500 message

  • Troubleshooting steps attempted

  • Windows OS version

  • Confirmation of firewall / proxy testing

  • AgentInstall.log

  • LGAgentScript_<timestamp>.log

  • Relevant Windows Event Viewer errors

  • Any EDR / AV exclusions applied

πŸ“Œ Providing logs upfront significantly reduces resolution time.


Summary 🀩

  • Error 500 during Windows Agent installation is typically endpoint-related, not server-side

  • Network security, TLS, EDR, or registration conflicts are common causes

  • The Liongard Agent Install Script is the recommended remediation

  • Logs generated by the script are essential for deeper troubleshooting

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