diff --git a/.github/workflows/test-windows.yml b/.github/workflows/test-windows.yml
index 9515dae8d..0dd96a6a6 100644
--- a/.github/workflows/test-windows.yml
+++ b/.github/workflows/test-windows.yml
@@ -59,7 +59,8 @@ jobs:
         run: |
           # We need to get the version here and make it an environment variable
           # It is used to install via bootstrap and in the test
-          # The version is in the instance name
+          # The version is in the instance name:
+          # ["stable-3006", "stable-3006-8", "stable-3007", "stable-3007-1", "latest"]
           $instance = "${{ matrix.instance }}"
           $version = $instance -split "-",2
           if ( $version.Count -gt 1 ) {
diff --git a/bootstrap-salt.ps1 b/bootstrap-salt.ps1
index afafb0aee..800ded032 100644
--- a/bootstrap-salt.ps1
+++ b/bootstrap-salt.ps1
@@ -207,25 +207,36 @@ function Get-AvailableVersions {
         Write-Verbose "- $_"
     }
 
-    # Get the latest version, should be the last in the list
-    Write-Verbose "Getting latest available version"
-    $latest = $available_versions | Select-Object -Last 1
-    Write-Verbose "Latest available version: $latest"
-
     # Create a versions table
     # This will have the latest version available, the latest version available
     # for each major version, and every version available. This makes the
     # version lookup logic easier. The contents of the versions table can be
     # found by running -Verbose
     Write-Verbose "Populating the versions table"
-    $versions_table = [ordered]@{"latest"=$latest}
+    $versions_table = [ordered]@{}
     $available_versions | ForEach-Object {
-        $versions_table[$(Get-MajorVersion $_)] = $_
+        $major_version = $(Get-MajorVersion $_)
+        if ( $versions_table.Keys -contains $major_version ) {
+            if ( [System.Version]$_ -gt [System.Version]$versions_table[$major_version] ) {
+                $versions_table[$major_version] = $_
+            }
+        } else {
+            $versions_table[$major_version] = $_
+        }
+
+        if ( $versions_table -contains "latest" ) {
+            if ( [System.Version]$_ -gt [System.Version]$versions_table["latest"] ) {
+                $versions_table["latest"] = $_
+            }
+        } else {
+            $versions_table["latest"] = $_
+        }
+
         $versions_table[$_.ToLower()] = $_.ToLower()
     }
 
     Write-Verbose "Versions Table:"
-    $versions_table | Sort-Object Name | Out-String | ForEach-Object {
+    $versions_table.GetEnumerator() | Sort-Object Name | Out-String | ForEach-Object {
         Write-Verbose "$_"
     }
 
diff --git a/tests/conftest.py b/tests/conftest.py
index 5d5702c12..4b34040e9 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -1,8 +1,9 @@
 import json
 import os
+import requests
+from packaging.version import Version
 
 import pytest
-import requests
 
 API_URL = (
     "https://packages.broadcom.com/artifactory/api/storage/saltproject-generic/windows"
@@ -27,9 +28,18 @@ def target_salt_version():
             version = folder["uri"].strip("/")
             versions[version] = version
             # We're trying to get the latest major version and latest overall
-            maj_version = version.split(".")[0]
-            versions[maj_version] = version
-            versions["latest"] = version
+            maj_ver, _ = version.split(".")
+            if maj_ver in versions:
+                if Version(version) > Version(versions[maj_ver]):
+                    versions[maj_ver] = version
+            else:
+                versions[maj_ver] = version
+
+            if "latest" in versions:
+                if Version(version) > Version(versions["latest"]):
+                    versions["latest"] = version
+            else:
+                versions["latest"] = version
 
     if target_salt.startswith("v"):
         target_salt = target_salt[1:]
diff --git a/tests/requirements.txt b/tests/requirements.txt
index 547de5c5b..2fc44ad6d 100644
--- a/tests/requirements.txt
+++ b/tests/requirements.txt
@@ -1,2 +1,3 @@
 pytest
 requests
+packaging