diff --git a/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py b/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py
index 0dd39dc..5d141b4 100644
--- a/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py
+++ b/Data/Agent/Roles/role_PlaybookExec_SYSTEM.py
@@ -20,12 +20,27 @@ def _project_root():
         return os.path.abspath(os.path.join(os.path.dirname(__file__), '..'))
 
 
+def _agent_root():
+    # Resolve Agent root at runtime.
+    # Typical runtime: <ProjectRoot>/Agent/Borealis/Roles/<this_file>
+    try:
+        here = os.path.abspath(os.path.dirname(__file__))
+        # Agent/Borealis/Roles -> Agent
+        return os.path.abspath(os.path.join(here, '..', '..', '..'))
+    except Exception:
+        return os.path.abspath(os.path.join(_project_root(), 'Agent'))
+
+
 def _scripts_bin():
-    # Return the venv Scripts (Windows) or bin (POSIX) path
-    base = os.path.join(_project_root(), 'Agent', 'Scripts')
-    if os.path.isdir(base):
-        return base
-    # Fallback to PATH
+    # Return the venv Scripts (Windows) or bin (POSIX) path adjacent to Borealis
+    agent_root = _agent_root()
+    candidates = [
+        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
     return None
 
 
@@ -38,12 +53,50 @@ def _ansible_playbook_cmd():
             return cand
     return exe
 
+def _ansible_galaxy_cmd():
+    exe = 'ansible-galaxy.exe' if os.name == 'nt' else 'ansible-galaxy'
+    sdir = _scripts_bin()
+    if sdir:
+        cand = os.path.join(sdir, exe)
+        if os.path.isfile(cand):
+            return cand
+    return exe
+
+def _collections_dir():
+    base = os.path.join(_project_root(), 'Agent', 'Borealis', 'AnsibleCollections')
+    try:
+        os.makedirs(base, exist_ok=True)
+    except Exception:
+        pass
+    return base
+
+def _venv_python():
+    try:
+        sdir = _scripts_bin()
+        if not sdir:
+            return None
+        cand = os.path.join(sdir, 'python.exe' if os.name == 'nt' else 'python3')
+        return cand if os.path.isfile(cand) else None
+    except Exception:
+        return None
+
 
 class Role:
     def __init__(self, ctx):
         self.ctx = ctx
         self._runs = {}  # run_id -> { proc, task, cancel }
 
+    def _log_local(self, msg: str, error: bool = False):
+        try:
+            base = os.path.join(_project_root(), 'Logs', 'Agent')
+            os.makedirs(base, exist_ok=True)
+            fn = 'agent.error.log' if error else 'agent.log'
+            ts = time.strftime('%Y-%m-%d %H:%M:%S')
+            with open(os.path.join(base, fn), 'a', encoding='utf-8') as fh:
+                fh.write(f'[{ts}] [PlaybookExec] {msg}\n')
+        except Exception:
+            pass
+
     def _server_base(self) -> str:
         try:
             fn = (self.ctx.hooks or {}).get('get_server_url')
@@ -62,8 +115,9 @@ class Role:
                 async with sess.post(url, json=payload) as resp:
                     # best-effort; ignore body
                     await resp.read()
+            self._log_local(f"Posted recap: run_id={payload.get('run_id')} status={payload.get('status')} bytes={len((payload.get('recap_text') or '').encode('utf-8'))}")
         except Exception:
-            pass
+            self._log_local(f"Failed to post recap for run_id={payload.get('run_id')}", error=True)
 
     async def _run_playbook_runner(self, run_id: str, playbook_content: str, playbook_name: str = '', activity_job_id=None, connection: str = 'local'):
         try:
@@ -205,7 +259,16 @@ class Role:
         conn = (connection or 'local').strip().lower()
         if conn not in ('local', 'winrm', 'psrp'):
             conn = 'local'
+        # Best-effort: if playbook uses ansible.windows, prefer psrp when connection left as local
+        if conn == 'local':
+            try:
+                if 'ansible.windows' in (playbook_content or ''):
+                    conn = 'psrp'
+            except Exception:
+                pass
+
         cmd = [_ansible_playbook_cmd(), path, '-i', 'localhost,', '-c', conn]
+        self._log_local(f"Launching ansible-playbook: conn={conn} cmd={' '.join(cmd)}")
         # Ensure clean, plain output and correct interpreter for localhost
         env = os.environ.copy()
         env.setdefault('ANSIBLE_FORCE_COLOR', '0')
@@ -214,6 +277,11 @@ class Role:
         env.setdefault('ANSIBLE_STDOUT_CALLBACK', 'default')
         # Help Ansible pick the correct python for localhost
         env.setdefault('ANSIBLE_LOCALHOST_WARNING', '0')
+        # Ensure collections path is discoverable
+        env.setdefault('ANSIBLE_COLLECTIONS_PATHS', _collections_dir())
+        vp = _venv_python()
+        if vp:
+            env.setdefault('ANSIBLE_PYTHON_INTERPRETER', vp)
 
         creationflags = 0
         if os.name == 'nt':
@@ -222,6 +290,17 @@ class Role:
 
         proc = None
         try:
+            # Best-effort collection install for windows modules
+            try:
+                if 'ansible.windows' in (playbook_content or ''):
+                    galaxy = _ansible_galaxy_cmd()
+                    coll_dir = _collections_dir()
+                    creation = 0x08000000 if os.name == 'nt' else 0
+                    self._log_local("Ensuring ansible.windows collection is installed for this agent")
+                    subprocess.run([galaxy, 'collection', 'install', 'ansible.windows', '-p', coll_dir], timeout=120, creationflags=creation)
+            except Exception:
+                self._log_local("Collection install failed (continuing)")
+
             # Prefer ansible-runner when available and enabled
             try:
                 if os.environ.get('BOREALIS_USE_ANSIBLE_RUNNER', '0').lower() not in ('0', 'false', 'no'):
@@ -240,6 +319,7 @@ class Role:
                 creationflags=creationflags,
             )
         except Exception as e:
+            self._log_local(f"Failed to launch ansible-playbook: {e}", error=True)
             await self._post_recap({
                 'run_id': run_id,
                 'hostname': hostname,
@@ -310,6 +390,7 @@ class Role:
                 pass
 
         rc = proc.returncode if proc else -1
+        self._log_local(f"ansible-playbook finished rc={rc}")
         status = 'Success' if rc == 0 else ('Cancelled' if self._runs.get(run_id, {}).get('cancel') else 'Failed')
 
         # Final recap text
diff --git a/Data/Server/WebUI/src/Devices/Device_Details.jsx b/Data/Server/WebUI/src/Devices/Device_Details.jsx
index 7f557e4..47bcbe5 100644
--- a/Data/Server/WebUI/src/Devices/Device_Details.jsx
+++ b/Data/Server/WebUI/src/Devices/Device_Details.jsx
@@ -826,6 +826,24 @@ export default function DeviceDetails({ device, onBack }) {
               </TableCell>
               <TableCell>
                 <Box sx={{ display: "flex", gap: 1 }}>
+                  {(String(r.script_type || '').toLowerCase() === 'ansible' && String(r.status||'') === 'Running') ? (
+                    <Button size="small" sx={{ color: "#ff6666", textTransform: "none", minWidth: 0, p: 0 }}
+                      onClick={async () => {
+                        try {
+                          const resp = await fetch(`/api/ansible/run_for_activity/${encodeURIComponent(r.id)}`);
+                          const data = await resp.json();
+                          if (!resp.ok) throw new Error(data.error || `HTTP ${resp.status}`);
+                          const run_id = data.run_id;
+                          if (run_id) {
+                            try { const s = window.BorealisSocket; s && s.emit('ansible_playbook_cancel', { run_id }); } catch {}
+                          } else {
+                            alert('Unable to locate run id for this playbook run.');
+                          }
+                        } catch (e) {
+                          alert(String(e.message || e));
+                        }
+                      }}>Cancel</Button>
+                  ) : null}
                   {r.has_stdout ? (
                     <Button size="small" onClick={() => handleViewOutput(r, 'stdout')} sx={{ color: "#58a6ff", textTransform: "none", minWidth: 0, p: 0 }}>
                       StdOut
diff --git a/Data/Server/server.py b/Data/Server/server.py
index 0abd59a..179a2eb 100644
--- a/Data/Server/server.py
+++ b/Data/Server/server.py
@@ -2566,7 +2566,34 @@ def ansible_quick_run():
 
         results = []
         for host in hostnames:
-            run_id = None
+            # Create activity_history row so UI shows running state and can receive recap mirror
+            job_id = None
+            try:
+                conn2 = _db_conn()
+                cur2 = conn2.cursor()
+                now_ts = int(time.time())
+                cur2.execute(
+                    """
+                    INSERT INTO activity_history(hostname, script_path, script_name, script_type, ran_at, status, stdout, stderr)
+                    VALUES(?,?,?,?,?,?,?,?)
+                    """,
+                    (
+                        str(host),
+                        rel_path.replace(os.sep, "/"),
+                        os.path.basename(abs_path),
+                        "ansible",
+                        now_ts,
+                        "Running",
+                        "",
+                        "",
+                    ),
+                )
+                job_id = cur2.lastrowid
+                conn2.commit()
+                conn2.close()
+            except Exception:
+                job_id = None
+
             try:
                 import uuid as _uuid
                 run_id = _uuid.uuid4().hex
@@ -2578,12 +2605,13 @@ def ansible_quick_run():
                 "playbook_name": os.path.basename(abs_path),
                 "playbook_content": content,
                 "connection": "local",
+                "activity_job_id": job_id,
             }
             try:
                 socketio.emit("ansible_playbook_run", payload)
             except Exception:
                 pass
-            results.append({"hostname": host, "run_id": run_id, "status": "Queued"})
+            results.append({"hostname": host, "run_id": run_id, "status": "Queued", "activity_job_id": job_id})
         return jsonify({"results": results})
     except ValueError as ve:
         return jsonify({"error": str(ve)}), 400
@@ -2839,6 +2867,26 @@ def api_ansible_recap_report():
         except Exception:
             pass
 
+        # Reflect into scheduled_job_runs if linked
+        try:
+            if scheduled_job_id and scheduled_run_id:
+                st = (status or '').strip()
+                ts_now = now
+                # If Running, update status/started_ts if needed; otherwise mark finished + status
+                if st.lower() == 'running':
+                    cur.execute(
+                        "UPDATE scheduled_job_runs SET status='Running', updated_at=?, started_ts=COALESCE(started_ts, ?) WHERE id=? AND job_id=?",
+                        (ts_now, started_ts or ts_now, int(scheduled_run_id), int(scheduled_job_id))
+                    )
+                else:
+                    cur.execute(
+                        "UPDATE scheduled_job_runs SET status=?, finished_ts=COALESCE(?, finished_ts, ?), updated_at=? WHERE id=? AND job_id=?",
+                        (st or 'Success', finished_ts, ts_now, ts_now, int(scheduled_run_id), int(scheduled_job_id))
+                    )
+                conn.commit()
+        except Exception:
+            pass
+
         # Return the latest row
         cur.execute(
             "SELECT id, run_id, hostname, agent_id, playbook_path, playbook_name, scheduled_job_id, scheduled_run_id, activity_job_id, status, recap_text, recap_json, started_ts, finished_ts, created_at, updated_at FROM ansible_play_recaps WHERE id=?",
@@ -2980,6 +3028,31 @@ def api_ansible_recap_get(recap_id: int):
         return jsonify({"error": str(e)}), 500
 
 
+@app.route("/api/ansible/run_for_activity/<int:activity_id>", methods=["GET"])
+def api_ansible_run_for_activity(activity_id: int):
+    """Return the latest run_id/status for a recap row linked to an activity_history id."""
+    try:
+        conn = _db_conn()
+        cur = conn.cursor()
+        cur.execute(
+            """
+            SELECT run_id, status
+            FROM ansible_play_recaps
+            WHERE activity_job_id = ?
+            ORDER BY COALESCE(updated_at, created_at) DESC, id DESC
+            LIMIT 1
+            """,
+            (activity_id,)
+        )
+        row = cur.fetchone()
+        conn.close()
+        if not row:
+            return jsonify({"error": "Not found"}), 404
+        return jsonify({"run_id": row[0], "status": row[1] or ""})
+    except Exception as e:
+        return jsonify({"error": str(e)}), 500
+
+
 @socketio.on("collector_status")
 def handle_collector_status(data):
     """Collector agent reports activity and optional last_user.