diff --git a/tracer/src/Datadog.FleetInstaller/Commands/CommandBase.cs b/tracer/src/Datadog.FleetInstaller/Commands/CommandBase.cs
index bf7882a3d1a2..79f4dc666e4a 100644
--- a/tracer/src/Datadog.FleetInstaller/Commands/CommandBase.cs
+++ b/tracer/src/Datadog.FleetInstaller/Commands/CommandBase.cs
@@ -6,6 +6,7 @@
 using System.CommandLine;
 using System.CommandLine.Invocation;
 using System.CommandLine.Parsing;
+using System.Diagnostics.CodeAnalysis;
 using System.Runtime.InteropServices;
 using System.Security.Principal;
 using System.Threading.Tasks;
@@ -35,18 +36,24 @@ protected bool IsValidEnvironment(CommandResult commandResult)
             return false;
         }
 
+        return true;
+    }
+
+    protected bool HasValidIIsVersion(ILogger commandResult, [NotNullWhen(false)] out string? errorMessage)
+    {
         if (!RegistryHelper.TryGetIisVersion(Log.Instance, out var version))
         {
-            commandResult.ErrorMessage = "This installer requires IIS 10.0 or later. Could not determine the IIS version; is the IIS feature enabled?";
+            errorMessage = "This installer requires IIS 10.0 or later. Could not determine the IIS version; is the IIS feature enabled?";
             return false;
         }
 
         if (version.Major < 10)
         {
-            commandResult.ErrorMessage = $"This installer requires IIS 10.0 or later. Detected IIS version {version.Major}.{version.Minor}";
+            errorMessage = $"This installer requires IIS 10.0 or later. Detected IIS version {version.Major}.{version.Minor}";
             return false;
         }
 
+        errorMessage = null;
         return true;
     }
 }
diff --git a/tracer/src/Datadog.FleetInstaller/Commands/InstallCommand.cs b/tracer/src/Datadog.FleetInstaller/Commands/InstallCommand.cs
index adaa27937b99..99e43df3d2fa 100644
--- a/tracer/src/Datadog.FleetInstaller/Commands/InstallCommand.cs
+++ b/tracer/src/Datadog.FleetInstaller/Commands/InstallCommand.cs
@@ -88,6 +88,12 @@ private void Validate(CommandResult commandResult)
             return;
         }
 
+        if (!HasValidIIsVersion(Log.Instance, out var errorMessage))
+        {
+            commandResult.ErrorMessage = errorMessage;
+            return;
+        }
+
         var path = commandResult.GetValueForOption(_versionedPathOption);
         if (path is not null && !FileHelper.TryVerifyFilesExist(Log.Instance, new TracerValues(path), out var err))
         {
diff --git a/tracer/src/Datadog.FleetInstaller/Commands/UninstallProductCommand.cs b/tracer/src/Datadog.FleetInstaller/Commands/UninstallProductCommand.cs
index 36572e116253..9509cd0a8c59 100644
--- a/tracer/src/Datadog.FleetInstaller/Commands/UninstallProductCommand.cs
+++ b/tracer/src/Datadog.FleetInstaller/Commands/UninstallProductCommand.cs
@@ -11,7 +11,7 @@
 namespace Datadog.FleetInstaller.Commands;
 
 /// <summary>
-/// Remove all version of the .NET tracer. Should be called for each version to be removed.
+/// Perform the final uninstall for the product
 /// </summary>
 internal class UninstallProductCommand : CommandBase
 {
@@ -33,17 +33,27 @@ public Task ExecuteAsync(InvocationContext context)
     }
 
     // Internal for testing
-    internal static ReturnCode Execute(ILogger log)
+    internal ReturnCode Execute(ILogger log)
     {
         log.WriteInfo("Uninstalling .NET tracer product");
 
-        // Remove the tracer references
-        if (!AppHostHelper.RemoveAllEnvironmentVariables(log))
+        if (!HasValidIIsVersion(log, out var errorMessage))
         {
-            // hard to be sure exactly of the state at this point,
-            // but probably don't want to do anything else if we couldn't remove the variables,
-            // as apps may fail
-            return ReturnCode.ErrorRemovingAppPoolVariables;
+            // IIS isn't available, weird because it means they removed it _after_ installing the product
+            // but whatever, there's no variables there if that's the case!
+            Log.Instance.WriteInfo(errorMessage);
+            Log.Instance.WriteInfo("Unable to uninstall from IIS, skipping IIS removal and continuing");
+        }
+        else
+        {
+            // Remove the tracer references
+            if (!AppHostHelper.RemoveAllEnvironmentVariables(log))
+            {
+                // hard to be sure exactly of the state at this point,
+                // but probably don't want to do anything else if we couldn't remove the variables,
+                // as apps may fail
+                return ReturnCode.ErrorRemovingAppPoolVariables;
+            }
         }
 
         // Should we clean up/delete the log folder? Probably not, as it may contain useful information