diff --git a/Borealis.ps1 b/Borealis.ps1
index c5f37b9..810e9a7 100644
--- a/Borealis.ps1
+++ b/Borealis.ps1
@@ -601,15 +601,67 @@ function Ensure-AnsibleExecutionEnvironment {
         $metadata['requirements_hash'] = $requirementsHash
     }
 
+    $supportDir = Join-Path $eeRoot 'support'
     try {
-        $metadata | ConvertTo-Json -Depth 5 | Set-Content -Path $metadataPath -Encoding UTF8
+        New-Item -ItemType Directory -Force -Path $supportDir | Out-Null
+    } catch {}
+
+    $fcntlStubPath = Join-Path $supportDir 'fcntl.py'
+    $fcntlStub = @'
+"""Compat shim for POSIX-only fcntl module.
+
+Generated by Borealis to allow Ansible tooling to run on Windows hosts
+where the standard library fcntl module is unavailable. The stub provides
+symbol constants and no-op function implementations so imports succeed.
+"""
+
+LOCK_SH = 1
+LOCK_EX = 2
+LOCK_UN = 8
+LOCK_NB = 4
+
+F_DUPFD = 0
+F_GETFD = 1
+F_SETFD = 2
+F_GETFL = 3
+F_SETFL = 4
+
+FD_CLOEXEC = 1
+
+def ioctl(*_args, **_kwargs):
+    return 0
+
+
+def fcntl(*_args, **_kwargs):
+    return 0
+
+
+def flock(*_args, **_kwargs):
+    return 0
+
+
+def lockf(*_args, **_kwargs):
+    return 0
+'@
+
+    try {
+        if (-not (Test-Path (Join-Path $supportDir '__init__.py') -PathType Leaf)) {
+            Set-Content -Path (Join-Path $supportDir '__init__.py') -Value '' -Encoding UTF8NoBOM
+        }
+        Set-Content -Path $fcntlStubPath -Value $fcntlStub -Encoding UTF8NoBOM
+    } catch {
+        Write-AgentLog -FileName $LogName -Message "[AnsibleEE] Failed to seed Windows fcntl compatibility shim: $($_.Exception.Message)"
+    }
+
+    try {
+        $metadata | ConvertTo-Json -Depth 5 | Set-Content -Path $metadataPath -Encoding UTF8NoBOM
     } catch {
         Write-AgentLog -FileName $LogName -Message "[AnsibleEE] Failed to persist metadata.json: $($_.Exception.Message)"
         throw "Unable to persist Ansible execution environment metadata."
     }
 
     try {
-        Set-Content -Path $versionTxtPath -Value $expectedVersionNorm -Encoding UTF8
+        Set-Content -Path $versionTxtPath -Value $expectedVersionNorm -Encoding UTF8NoBOM
     } catch {}
 
     Write-AgentLog -FileName $LogName -Message "[AnsibleEE] Execution environment ready at $eeRoot"
diff --git a/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py b/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py
index 2238398..62a7fb4 100644
--- a/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py
+++ b/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py
@@ -178,6 +178,16 @@ def _scripts_bin():
     return None
 
 
+def _ee_support_path():
+    root = _ansible_ee_root()
+    if not root:
+        return None
+    support = os.path.join(root, 'support')
+    if os.path.isdir(support):
+        return support
+    return None
+
+
 def _ansible_playbook_cmd():
     exe = 'ansible-playbook.exe' if os.name == 'nt' else 'ansible-playbook'
     sdir = _scripts_bin()
@@ -341,6 +351,19 @@ class Role:
         version = _ansible_ee_version()
         if version:
             self._ansible_log(f"[bootstrap] using execution environment version {version}")
+
+        support_dir = _ee_support_path()
+        if support_dir:
+            existing_pp = os.environ.get('PYTHONPATH') or ''
+            paths = [seg for seg in existing_pp.split(os.pathsep) if seg]
+            if support_dir not in paths:
+                os.environ['PYTHONPATH'] = (
+                    support_dir
+                    if not existing_pp
+                    else support_dir + os.pathsep + existing_pp
+                )
+            os.environ['BOREALIS_ANSIBLE_EE_SUPPORT'] = support_dir
+
         return True
 
     async def _ensure_ansible_ready(self) -> bool: