diff --git a/Borealis.ps1 b/Borealis.ps1
index e1fde6a..b4527d8 100644
--- a/Borealis.ps1
+++ b/Borealis.ps1
@@ -256,6 +256,19 @@ $nodeExe    = Join-Path $depsRoot 'NodeJS\node.exe'
 $sevenZipExe    = Join-Path $depsRoot "7zip\7z.exe"
 $npmCmd     = Join-Path (Split-Path $nodeExe) 'npm.cmd'
 $npxCmd     = Join-Path (Split-Path $nodeExe) 'npx.cmd'
+$ansibleEeRequirementsPath = Join-Path $scriptDir 'Data\Agent\ansible-ee-requirements.txt'
+$ansibleEeVersionFile      = Join-Path $scriptDir 'Data\Agent\ansible-ee-version.txt'
+$script:AnsibleExecutionEnvironmentVersion = '1.0.0'
+if (Test-Path $ansibleEeVersionFile -PathType Leaf) {
+    try {
+        $rawVersion = (Get-Content -Path $ansibleEeVersionFile -Raw -ErrorAction Stop)
+        if ($rawVersion) {
+            $script:AnsibleExecutionEnvironmentVersion = ($rawVersion.Split("`n")[0]).Trim()
+        }
+    } catch {
+        # Leave default version value
+    }
+}
 $node7zUrl      = "https://nodejs.org/dist/v23.11.0/node-v23.11.0-win-x64.7z"
 $nodeInstallDir = Join-Path $depsRoot "NodeJS"
 $node7zPath     = Join-Path $depsRoot "node-v23.11.0-win-x64.7z"
@@ -449,6 +462,139 @@ function Install_Agent_Dependencies {
     }
 }
 
+function Ensure-AnsibleExecutionEnvironment {
+    param(
+        [Parameter(Mandatory = $true)]
+        [string]$ProjectRoot,
+
+        [Parameter(Mandatory = $true)]
+        [string]$PythonBootstrapExe,
+
+        [string]$RequirementsPath,
+        [string]$ExpectedVersion = '1.0.0',
+        [string]$LogName = 'Install.log'
+    )
+
+    if (-not (Test-Path $PythonBootstrapExe -PathType Leaf)) {
+        Write-AgentLog -FileName $LogName -Message "[AnsibleEE] Bundled python executable missing at $PythonBootstrapExe"
+        throw "Bundled python executable not found for Ansible execution environment provisioning."
+    }
+
+    $eeRoot = Join-Path $ProjectRoot 'Agent\Ansible_EE'
+    $metadataPath = Join-Path $eeRoot 'metadata.json'
+    $versionTxtPath = Join-Path $eeRoot 'version.txt'
+
+    $requirementsHash = ''
+    if ($RequirementsPath -and (Test-Path $RequirementsPath -PathType Leaf)) {
+        try {
+            $requirementsHash = (Get-FileHash -Path $RequirementsPath -Algorithm SHA256).Hash
+        } catch {
+            $requirementsHash = ''
+        }
+    }
+
+    $currentVersion = ''
+    $currentHash = ''
+    if (Test-Path $metadataPath -PathType Leaf) {
+        try {
+            $metaRaw = Get-Content -Path $metadataPath -Raw -ErrorAction Stop
+            if ($metaRaw) {
+                $meta = $metaRaw | ConvertFrom-Json -ErrorAction Stop
+                if ($meta.version) {
+                    $currentVersion = ($meta.version).ToString().Trim()
+                }
+                if ($meta.requirements_hash) {
+                    $currentHash = ($meta.requirements_hash).ToString().Trim()
+                } elseif ($meta.requirements_sha256) {
+                    $currentHash = ($meta.requirements_sha256).ToString().Trim()
+                }
+            }
+        } catch {
+            $currentVersion = ''
+            $currentHash = ''
+        }
+    }
+
+    $pythonCandidates = @(
+        Join-Path $eeRoot 'Scripts\python.exe',
+        Join-Path $eeRoot 'Scripts\python3.exe',
+        Join-Path $eeRoot 'bin\python3',
+        Join-Path $eeRoot 'bin\python'
+    )
+
+    $existingPython = $pythonCandidates | Where-Object { Test-Path $_ -PathType Leaf } | Select-Object -First 1
+
+    $expectedVersionNorm = ($ExpectedVersion ?? '1.0.0').Trim()
+    $isUpToDate = $false
+    if ($existingPython -and $currentVersion -and ($currentVersion -eq $expectedVersionNorm)) {
+        if (-not $requirementsHash -or ($currentHash -and $currentHash -eq $requirementsHash)) {
+            $isUpToDate = $true
+        }
+    }
+
+    if ($isUpToDate) {
+        Write-AgentLog -FileName $LogName -Message "[AnsibleEE] Existing execution environment is up-to-date (version $currentVersion)."
+        return
+    }
+
+    Write-AgentLog -FileName $LogName -Message "[AnsibleEE] Provisioning execution environment version $expectedVersionNorm."
+
+    if (Test-Path $eeRoot) {
+        try { Remove-Item -Path $eeRoot -Recurse -Force -ErrorAction Stop } catch {}
+    }
+    New-Item -ItemType Directory -Force -Path $eeRoot | Out-Null
+
+    & $PythonBootstrapExe -m venv $eeRoot | Out-Null
+    if ($LASTEXITCODE -ne 0) {
+        Write-AgentLog -FileName $LogName -Message "[AnsibleEE] python -m venv failed with exit code $LASTEXITCODE"
+        throw "Failed to create Ansible execution environment virtual environment."
+    }
+
+    $pythonExe = $pythonCandidates | Where-Object { Test-Path $_ -PathType Leaf } | Select-Object -First 1
+    if (-not $pythonExe) {
+        Write-AgentLog -FileName $LogName -Message "[AnsibleEE] Unable to locate python executable inside execution environment."
+        throw "Ansible execution environment python executable missing after provisioning."
+    }
+
+    & $pythonExe -m pip install --upgrade pip setuptools wheel --disable-pip-version-check | Out-Null
+    if ($LASTEXITCODE -ne 0) {
+        Write-AgentLog -FileName $LogName -Message "[AnsibleEE] pip bootstrap failed with exit code $LASTEXITCODE"
+        throw "Failed to bootstrap pip inside the Ansible execution environment."
+    }
+
+    if ($RequirementsPath -and (Test-Path $RequirementsPath -PathType Leaf)) {
+        & $pythonExe -m pip install --disable-pip-version-check -r $RequirementsPath | Out-Null
+        if ($LASTEXITCODE -ne 0) {
+            Write-AgentLog -FileName $LogName -Message "[AnsibleEE] pip install -r requirements failed with exit code $LASTEXITCODE"
+            throw "Failed to install Ansible execution environment requirements."
+        }
+    } else {
+        Write-AgentLog -FileName $LogName -Message "[AnsibleEE] Requirements file not found; skipping dependency installation."
+    }
+
+    $metadata = [ordered]@{
+        version = $expectedVersionNorm
+        created_utc = (Get-Date).ToUniversalTime().ToString('o')
+        python = $pythonExe
+    }
+    if ($requirementsHash) {
+        $metadata['requirements_hash'] = $requirementsHash
+    }
+
+    try {
+        $metadata | ConvertTo-Json -Depth 5 | Set-Content -Path $metadataPath -Encoding UTF8
+    } 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
+    } catch {}
+
+    Write-AgentLog -FileName $LogName -Message "[AnsibleEE] Execution environment ready at $eeRoot"
+}
+
 function Ensure-AgentTasks {
     param([string]$ScriptRoot)
     $pyw         = Join-Path $ScriptRoot 'Agent\Scripts\pythonw.exe'
@@ -569,6 +715,15 @@ function InstallOrUpdate-BorealisAgent {
         }
     }
 
+    Run-Step "Provision Ansible Execution Environment" {
+        Ensure-AnsibleExecutionEnvironment \
+            -ProjectRoot $scriptDir \
+            -PythonBootstrapExe $pythonExe \
+            -RequirementsPath $ansibleEeRequirementsPath \
+            -ExpectedVersion $script:AnsibleExecutionEnvironmentVersion \
+            -LogName 'Install.log'
+    }
+
     Run-Step "Configure Agent Settings" {
         $settingsDir = Join-Path $scriptDir 'Agent\Borealis\Settings'
         $oldSettingsDir = Join-Path $scriptDir 'Agent\Settings'
diff --git a/Data/Agent/Roles/role_DeviceAudit.py b/Data/Agent/Roles/role_DeviceAudit.py
index d78b3fd..c5e646d 100644
--- a/Data/Agent/Roles/role_DeviceAudit.py
+++ b/Data/Agent/Roles/role_DeviceAudit.py
@@ -229,18 +229,55 @@ def detect_agent_os():
         return "Unknown"
 
 
+def _ansible_ee_version():
+    try:
+        root = _project_root()
+        meta_path = os.path.join(root, 'Ansible_EE', 'metadata.json')
+        if os.path.isfile(meta_path):
+            try:
+                with open(meta_path, 'r', encoding='utf-8') as fh:
+                    data = json.load(fh)
+                if isinstance(data, dict):
+                    for key in ('version', 'ansible_ee_ver', 'ansible_ee_version'):
+                        value = data.get(key)
+                        if isinstance(value, (str, int, float)):
+                            text = str(value).strip()
+                            if text:
+                                return text
+            except Exception:
+                pass
+        version_txt = os.path.join(root, 'Ansible_EE', 'version.txt')
+        if os.path.isfile(version_txt):
+            try:
+                raw = Path(version_txt).read_text(encoding='utf-8')
+                if raw:
+                    text = raw.splitlines()[0].strip()
+                    if text:
+                        return text
+            except Exception:
+                pass
+    except Exception:
+        pass
+    return ''
+
+
 def collect_summary(CONFIG):
     try:
         hostname = socket.gethostname()
-        return {
+        summary = {
             'hostname': hostname,
             'os': detect_agent_os(),
             'username': os.environ.get('USERNAME') or os.environ.get('USER') or '',
             'domain': os.environ.get('USERDOMAIN') or '',
             'uptime_sec': int(time.time() - psutil.boot_time()) if psutil else None,
         }
+        summary['ansible_ee_ver'] = _ansible_ee_version()
+        return summary
     except Exception:
-        return {'hostname': socket.gethostname()}
+        return {
+            'hostname': socket.gethostname(),
+            'ansible_ee_ver': _ansible_ee_version(),
+        }
 
 
 def _project_root():
diff --git a/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py b/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py
index 2c05cca..f27ec29 100644
--- a/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py
+++ b/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py
@@ -8,6 +8,7 @@ import json
 import socket
 import subprocess
 import base64
+from pathlib import Path
 from typing import Optional
 
 try:
@@ -53,6 +54,62 @@ def _project_root():
         return os.path.abspath(os.path.join(os.path.dirname(__file__), '..'))
 
 
+def _ansible_ee_root():
+    candidates = []
+    try:
+        candidates.append(os.path.join(_project_root(), 'Agent', 'Ansible_EE'))
+    except Exception:
+        pass
+    try:
+        candidates.append(os.path.join(_agent_root(), 'Ansible_EE'))
+    except Exception:
+        pass
+    for path in candidates:
+        if path and os.path.isdir(path):
+            return path
+    return None
+
+
+def _ansible_ee_metadata():
+    root = _ansible_ee_root()
+    if not root:
+        return {}
+    meta_path = os.path.join(root, 'metadata.json')
+    if not os.path.isfile(meta_path):
+        return {}
+    try:
+        with open(meta_path, 'r', encoding='utf-8') as fh:
+            data = json.load(fh)
+        if isinstance(data, dict):
+            return data
+    except Exception:
+        return {}
+    return {}
+
+
+def _ansible_ee_version():
+    meta = _ansible_ee_metadata()
+    for key in ('version', 'ansible_ee_ver', 'ansible_ee_version'):
+        value = meta.get(key) if isinstance(meta, dict) else None
+        if isinstance(value, (str, int, float)):
+            text = str(value).strip()
+            if text:
+                return text
+    root = _ansible_ee_root()
+    if root:
+        txt_path = os.path.join(root, 'version.txt')
+        if os.path.isfile(txt_path):
+            try:
+                raw = Path(txt_path).read_text(encoding='utf-8')
+                if raw:
+                    text = raw.splitlines()[0].strip()
+                    if text:
+                        return text
+            except Exception:
+                pass
+    return ''
+
+
 def _decode_base64_text(value):
     if not isinstance(value, str):
         return None
@@ -99,11 +156,22 @@ def _agent_root():
 
 def _scripts_bin():
     # Return the venv Scripts (Windows) or bin (POSIX) path adjacent to Borealis
+    candidates = []
+    ee_root = _ansible_ee_root()
+    if ee_root:
+        candidates.extend(
+            [
+                os.path.join(ee_root, 'Scripts'),
+                os.path.join(ee_root, 'bin'),
+            ]
+        )
     agent_root = _agent_root()
-    candidates = [
-        os.path.join(agent_root, 'Scripts'),  # Windows venv
-        os.path.join(agent_root, 'bin'),      # POSIX venv
-    ]
+    candidates.extend(
+        [
+            os.path.join(agent_root, 'Scripts'),  # Windows venv
+            os.path.join(agent_root, 'bin'),      # POSIX venv
+        ]
+    )
     for base in candidates:
         if os.path.isdir(base):
             return base
@@ -137,10 +205,19 @@ def _collections_dir():
     return base
 
 def _venv_python():
+    ee_root = _ansible_ee_root()
+    if ee_root:
+        ee_candidates = [
+            os.path.join(ee_root, 'Scripts', 'python.exe'),
+            os.path.join(ee_root, 'Scripts', 'python3.exe'),
+            os.path.join(ee_root, 'bin', 'python3'),
+            os.path.join(ee_root, 'bin', 'python'),
+        ]
+        for cand in ee_candidates:
+            if os.path.isfile(cand):
+                return cand
     try:
-        sdir = _scripts_bin()
-        if not sdir:
-            return None
+        sdir = os.path.join(_agent_root(), 'Scripts' if os.name == 'nt' else 'bin')
         cand = os.path.join(sdir, 'python.exe' if os.name == 'nt' else 'python3')
         return cand if os.path.isfile(cand) else None
     except Exception:
@@ -185,40 +262,55 @@ class Role:
 
     def _bootstrap_ansible_sync(self) -> bool:
         missing = self._detect_missing_modules()
-        if not missing:
-            return True
-        specs = sorted({spec for spec in missing.values() if spec})
-        python_exe = _venv_python() or sys.executable
-        if not python_exe:
-            self._ansible_log('[bootstrap] python executable not found for pip install', error=True)
+        if missing:
+            self._ansible_log(
+                f"[bootstrap] required agent modules missing: {', '.join(sorted(missing.keys()))}",
+                error=True,
+            )
             return False
-        cmd = [python_exe, '-m', 'pip', 'install', '--disable-pip-version-check'] + specs
-        self._ansible_log(f"[bootstrap] ensuring modules via pip: {', '.join(specs)}")
-        try:
-            result = subprocess.run(cmd, capture_output=True, text=True, timeout=900)
-        except Exception as exc:
-            self._ansible_log(f"[bootstrap] pip install exception: {exc}", error=True)
+        ee_root = _ansible_ee_root()
+        if not ee_root or not os.path.isdir(ee_root):
+            self._ansible_log('[bootstrap] execution environment folder Agent/Ansible_EE not found', error=True)
             return False
-        if result.returncode != 0:
-            err_tail = (result.stderr or '').strip()
-            if len(err_tail) > 500:
-                err_tail = err_tail[-500:]
-            self._ansible_log(f"[bootstrap] pip install failed rc={result.returncode} err={err_tail}", error=True)
+
+        scripts_dir = _scripts_bin()
+        exe_name = 'ansible-playbook.exe' if os.name == 'nt' else 'ansible-playbook'
+        playbook_path = None
+        if scripts_dir:
+            candidate = os.path.join(scripts_dir, exe_name)
+            if os.path.isfile(candidate):
+                playbook_path = candidate
+        if not playbook_path:
+            self._ansible_log('[bootstrap] ansible-playbook executable missing in execution environment', error=True)
             return False
-        remaining = self._detect_missing_modules()
-        if remaining:
-            self._ansible_log(f"[bootstrap] modules still missing after install: {', '.join(sorted(remaining.keys()))}", error=True)
+
+        python_exe = _venv_python()
+        if not python_exe or not os.path.isfile(python_exe):
+            self._ansible_log('[bootstrap] execution environment python not found', error=True)
             return False
-        try:
-            marker = self._bootstrap_marker_path()
-            payload = {
-                'timestamp': int(time.time()),
-                'modules': specs,
-            }
-            with open(marker, 'w', encoding='utf-8') as fh:
-                json.dump(payload, fh)
-        except Exception:
-            pass
+
+        env_path = os.environ.get('PATH') or ''
+        bin_dir = os.path.dirname(playbook_path)
+        if bin_dir:
+            segments = [seg for seg in env_path.split(os.pathsep) if seg]
+            if bin_dir not in segments:
+                os.environ['PATH'] = bin_dir + (os.pathsep + env_path if env_path else '')
+
+        collections_dir = os.path.join(ee_root, 'collections')
+        if os.path.isdir(collections_dir):
+            existing = os.environ.get('ANSIBLE_COLLECTIONS_PATHS') or ''
+            paths = [seg for seg in existing.split(os.pathsep) if seg]
+            if collections_dir not in paths:
+                os.environ['ANSIBLE_COLLECTIONS_PATHS'] = (
+                    collections_dir if not existing else collections_dir + os.pathsep + existing
+                )
+
+        os.environ['BOREALIS_ANSIBLE_EE_ROOT'] = ee_root
+        os.environ['BOREALIS_ANSIBLE_EE_PYTHON'] = python_exe
+
+        version = _ansible_ee_version()
+        if version:
+            self._ansible_log(f"[bootstrap] using execution environment version {version}")
         return True
 
     async def _ensure_ansible_ready(self) -> bool:
diff --git a/Data/Agent/ansible-ee-requirements.txt b/Data/Agent/ansible-ee-requirements.txt
new file mode 100644
index 0000000..8bebb6b
--- /dev/null
+++ b/Data/Agent/ansible-ee-requirements.txt
@@ -0,0 +1,8 @@
+#////////// PROJECT FILE SEPARATION LINE ////////// CODE AFTER THIS LINE ARE FROM: <ProjectRoot>/Data/Agent/ansible-ee-requirements.txt
+# Ansible execution environment dependencies
+ansible-core==2.16.7
+ansible-runner==2.3.5
+pywinrm==0.4.3
+requests-credssp==2.0.0
+requests-ntlm==1.2.0
+pypsrp==0.8.1
diff --git a/Data/Agent/ansible-ee-version.txt b/Data/Agent/ansible-ee-version.txt
new file mode 100644
index 0000000..9980c20
--- /dev/null
+++ b/Data/Agent/ansible-ee-version.txt
@@ -0,0 +1,2 @@
+#////////// PROJECT FILE SEPARATION LINE ////////// CODE AFTER THIS LINE ARE FROM: <ProjectRoot>/Data/Agent/ansible-ee-version.txt
+1.0.0
diff --git a/Data/Server/server.py b/Data/Server/server.py
index 8b6d2ad..b111e9c 100644
--- a/Data/Server/server.py
+++ b/Data/Server/server.py
@@ -3514,6 +3514,7 @@ _DEVICE_TABLE_COLUMNS = [
     "operating_system",
     "uptime",
     "agent_id",
+    "ansible_ee_ver",
     "connection_type",
     "connection_endpoint",
 ]
@@ -3603,6 +3604,7 @@ def _assemble_device_snapshot(record: Dict[str, Any]) -> Dict[str, Any]:
         "created": _ts_to_human(created_ts),
         "connection_type": _clean_device_str(record.get("connection_type")) or "",
         "connection_endpoint": _clean_device_str(record.get("connection_endpoint")) or "",
+        "ansible_ee_ver": _clean_device_str(record.get("ansible_ee_ver")) or "",
     }
 
     details = {
@@ -3747,6 +3749,7 @@ def _extract_device_columns(details: Dict[str, Any]) -> Dict[str, Any]:
     )
     payload["uptime"] = _coerce_int(uptime_value)
     payload["agent_id"] = _clean_device_str(summary.get("agent_id"))
+    payload["ansible_ee_ver"] = _clean_device_str(summary.get("ansible_ee_ver"))
     payload["connection_type"] = _clean_device_str(
         summary.get("connection_type")
         or summary.get("remote_type")
@@ -3815,9 +3818,10 @@ def _device_upsert(
             operating_system,
             uptime,
             agent_id,
+            ansible_ee_ver,
             connection_type,
             connection_endpoint
-        ) VALUES (?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?)
+        ) VALUES (?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?)
         ON CONFLICT(hostname) DO UPDATE SET
             description=excluded.description,
             created_at=COALESCE({DEVICE_TABLE}.created_at, excluded.created_at),
@@ -3838,6 +3842,7 @@ def _device_upsert(
             operating_system=COALESCE(NULLIF(excluded.operating_system, ''), {DEVICE_TABLE}.operating_system),
             uptime=COALESCE(NULLIF(excluded.uptime, 0), {DEVICE_TABLE}.uptime),
             agent_id=COALESCE(NULLIF(excluded.agent_id, ''), {DEVICE_TABLE}.agent_id),
+            ansible_ee_ver=COALESCE(NULLIF(excluded.ansible_ee_ver, ''), {DEVICE_TABLE}.ansible_ee_ver),
             connection_type=COALESCE(NULLIF(excluded.connection_type, ''), {DEVICE_TABLE}.connection_type),
             connection_endpoint=COALESCE(NULLIF(excluded.connection_endpoint, ''), {DEVICE_TABLE}.connection_endpoint)
     """
@@ -3863,6 +3868,7 @@ def _device_upsert(
         column_values.get("operating_system"),
         column_values.get("uptime"),
         column_values.get("agent_id"),
+        column_values.get("ansible_ee_ver"),
         column_values.get("connection_type"),
         column_values.get("connection_endpoint"),
     ]
@@ -4160,7 +4166,10 @@ def init_db():
                     last_user TEXT,
                     operating_system TEXT,
                     uptime INTEGER,
-                    agent_id TEXT
+                    agent_id TEXT,
+                    ansible_ee_ver TEXT,
+                    connection_type TEXT,
+                    connection_endpoint TEXT
                 )
                 """
             )
@@ -4193,6 +4202,7 @@ def init_db():
     _ensure_column("operating_system", "TEXT")
     _ensure_column("uptime", "INTEGER")
     _ensure_column("agent_id", "TEXT")
+    _ensure_column("ansible_ee_ver", "TEXT")
     _ensure_column("connection_type", "TEXT")
     _ensure_column("connection_endpoint", "TEXT")
 
@@ -4274,6 +4284,7 @@ def init_db():
                         operating_system TEXT,
                         uptime INTEGER,
                         agent_id TEXT,
+                        ansible_ee_ver TEXT,
                         connection_type TEXT,
                         connection_endpoint TEXT
                     )
diff --git a/Update.ps1 b/Update.ps1
index 212ac56..fdd631c 100644
--- a/Update.ps1
+++ b/Update.ps1
@@ -497,6 +497,8 @@ function Invoke-BorealisUpdate {
 
     $preservePath = Join-Path $scriptDir "Data\Server\Python_API_Endpoints\Tesseract-OCR"
     $preserveBackupPath = Join-Path $scriptDir "Update_Staging\Tesseract-OCR"
+    $ansibleEePath = Join-Path $scriptDir "Agent\Ansible_EE"
+    $ansibleEeBackupPath = Join-Path $scriptDir "Update_Staging\Ansible_EE"
 
     Run-Step "Updating: Move Tesseract-OCR Folder Somewhere Safe to Restore Later" {
         if (Test-Path $preservePath) {
@@ -506,6 +508,17 @@ function Invoke-BorealisUpdate {
         }
     }
 
+    Run-Step "Updating: Preserve Ansible Execution Environment" {
+        if (Test-Path $ansibleEePath) {
+            $stagingPath = Join-Path $scriptDir "Update_Staging"
+            if (-not (Test-Path $stagingPath)) { New-Item -ItemType Directory -Force -Path $stagingPath | Out-Null }
+            if (Test-Path $ansibleEeBackupPath) {
+                Remove-Item -Path $ansibleEeBackupPath -Recurse -Force -ErrorAction SilentlyContinue
+            }
+            Move-Item -Path $ansibleEePath -Destination $ansibleEeBackupPath -Force
+        }
+    }
+
     Run-Step "Updating: Clean Up Folders to Prepare for Update" {
         Remove-Item -Recurse -Force -ErrorAction SilentlyContinue `
             (Join-Path $scriptDir "Data"), `
@@ -575,6 +588,14 @@ function Invoke-BorealisUpdate {
         }
     }
 
+    Run-Step "Updating: Restore Ansible Execution Environment" {
+        $restorePath = Join-Path $scriptDir "Agent"
+        if (Test-Path $ansibleEeBackupPath) {
+            if (-not (Test-Path $restorePath)) { New-Item -ItemType Directory -Force -Path $restorePath | Out-Null }
+            Move-Item -Path $ansibleEeBackupPath -Destination $restorePath -Force
+        }
+    }
+
     Run-Step "Updating: Clean Up Update Staging Folder" {
         Remove-Item -Recurse -Force -ErrorAction SilentlyContinue $stagingPath
     }