diff --git a/cheddahbot/scheduler.py b/cheddahbot/scheduler.py
index 4e4ce7b..47ecfd6 100644
--- a/cheddahbot/scheduler.py
+++ b/cheddahbot/scheduler.py
@@ -1,12 +1,14 @@
-"""Task scheduler with heartbeat and ClickUp polling support."""
+"""Task scheduler with heartbeat, ClickUp polling, and folder watch support."""
 
 from __future__ import annotations
 
 import json
 import logging
 import re
+import shutil
 import threading
 from datetime import UTC, datetime
+from pathlib import Path
 from typing import TYPE_CHECKING
 
 from croniter import croniter
@@ -31,6 +33,9 @@ def _extract_docx_paths(result: str) -> list[str]:
 
 
 class Scheduler:
+    # Tasks due within this window are eligible for execution
+    DUE_DATE_WINDOW_WEEKS = 3
+
     def __init__(
         self,
         config: Config,
@@ -46,7 +51,9 @@ class Scheduler:
         self._thread: threading.Thread | None = None
         self._heartbeat_thread: threading.Thread | None = None
         self._clickup_thread: threading.Thread | None = None
+        self._folder_watch_thread: threading.Thread | None = None
         self._clickup_client = None
+        self._field_filter_cache: dict | None = None
 
     def start(self):
         """Start the scheduler, heartbeat, and ClickUp threads."""
@@ -70,6 +77,21 @@ class Scheduler:
         else:
             log.info("ClickUp integration disabled (no API token)")
 
+        # Start folder watcher if configured
+        watch_folder = self.config.link_building.watch_folder
+        if watch_folder:
+            self._folder_watch_thread = threading.Thread(
+                target=self._folder_watch_loop, daemon=True, name="folder-watch"
+            )
+            self._folder_watch_thread.start()
+            log.info(
+                "Folder watcher started (folder=%s, interval=%dm)",
+                watch_folder,
+                self.config.link_building.watch_interval_minutes,
+            )
+        else:
+            log.info("Folder watcher disabled (no watch_folder configured)")
+
         log.info(
             "Scheduler started (poll=%ds, heartbeat=%dm)",
             self.config.scheduler.poll_interval_seconds,
@@ -175,165 +197,159 @@ class Scheduler:
         # Wait before first poll to let other systems initialize
         self._stop_event.wait(30)
 
-        # On startup, recover orphaned executing tasks
-        self._recover_orphaned_tasks()
-
         while not self._stop_event.is_set():
             try:
                 self._poll_clickup()
-                self._execute_approved_tasks()
             except Exception as e:
                 log.error("ClickUp poll error: %s", e)
             self._stop_event.wait(interval)
 
-    def _recover_orphaned_tasks(self):
-        """Reset tasks stuck in 'executing' state (from crash/restart) to 'approved'."""
-        pairs = self.db.kv_scan("clickup:task:")
-        for key, value in pairs:
-            if not key.endswith(":state"):
-                continue
-            try:
-                state = json.loads(value)
-                if state.get("state") == "executing":
-                    task_id = state["clickup_task_id"]
-                    log.warning("Recovering orphaned executing task: %s", task_id)
-                    state["state"] = "approved"
-                    state["error"] = None
-                    self.db.kv_set(key, json.dumps(state))
-            except (json.JSONDecodeError, KeyError):
-                pass
+    def _discover_field_filter(self, client):
+        """Discover and cache the Work Category field UUID + option map."""
+        space_id = self.config.clickup.space_id
+        list_ids = client.get_list_ids_from_space(space_id)
+        if not list_ids:
+            log.warning("No lists found in space %s — cannot discover field filter", space_id)
+            return None
+
+        # Use the first list to discover field metadata
+        first_list = next(iter(list_ids))
+        field_name = self.config.clickup.task_type_field_name
+        result = client.discover_field_filter(first_list, field_name)
+        if result:
+            log.info(
+                "Discovered field filter for '%s': field_id=%s, options=%s",
+                field_name,
+                result["field_id"],
+                list(result["options"].keys()),
+            )
+        else:
+            log.warning(
+                "Field '%s' not found in list %s — falling back to client-side filtering",
+                field_name,
+                first_list,
+            )
+        return result
 
     def _poll_clickup(self):
-        """Discover new tasks from ClickUp and process them."""
+        """Poll ClickUp for eligible tasks and execute them immediately."""
         client = self._get_clickup_client()
         space_id = self.config.clickup.space_id
         if not space_id:
             log.warning("ClickUp space_id not configured, skipping poll")
             return
 
+        skill_map = self.config.clickup.skill_map
+        if not skill_map:
+            log.debug("No skill_map configured, skipping ClickUp poll")
+            return
+
+        # Discover field filter on first poll
+        if self._field_filter_cache is None:
+            self._field_filter_cache = self._discover_field_filter(client) or {}
+
+        # Build API filters
+        now_ms = int(datetime.now(UTC).timestamp() * 1000)
+        due_date_lt = now_ms + (self.DUE_DATE_WINDOW_WEEKS * 7 * 24 * 60 * 60 * 1000)
+
+        custom_fields_filter = None
+        if self._field_filter_cache and self._field_filter_cache.get("options"):
+            field_id = self._field_filter_cache["field_id"]
+            options = self._field_filter_cache["options"]
+            # Only include options that map to skills we have
+            matching_opt_ids = [
+                options[name] for name in skill_map if name in options
+            ]
+            if matching_opt_ids:
+                import json as _json
+
+                custom_fields_filter = _json.dumps(
+                    [{"field_id": field_id, "operator": "ANY", "value": matching_opt_ids}]
+                )
+
         tasks = client.get_tasks_from_space(
             space_id,
             statuses=self.config.clickup.poll_statuses,
+            due_date_lt=due_date_lt,
+            custom_fields=custom_fields_filter,
         )
 
-        # Load active task IDs to avoid re-processing
-        active_raw = self.db.kv_get("clickup:active_task_ids")
-        active_ids: set[str] = set(json.loads(active_raw)) if active_raw else set()
-
         for task in tasks:
-            if task.id in active_ids:
-                continue  # Already tracked
-            self._process_clickup_task(task, active_ids)
+            # Skip tasks already processed in kv_store
+            raw = self.db.kv_get(f"clickup:task:{task.id}:state")
+            if raw:
+                try:
+                    existing = json.loads(raw)
+                    if existing.get("state") in ("executing", "completed", "failed"):
+                        continue
+                except json.JSONDecodeError:
+                    pass
 
-        # Save updated active IDs
-        self.db.kv_set("clickup:active_task_ids", json.dumps(list(active_ids)))
+            # Client-side verify: Work Category must be in skill_map
+            if task.task_type not in skill_map:
+                continue
 
-    def _process_clickup_task(self, task, active_ids: set[str]):
-        """Discover a new ClickUp task, map to skill, decide action."""
+            # Client-side verify: due_date must exist and be within window
+            if not task.due_date:
+                continue
+            try:
+                task_due_ms = int(task.due_date)
+                if task_due_ms > due_date_lt:
+                    continue
+            except (ValueError, TypeError):
+                continue
 
-        now = datetime.now(UTC).isoformat()
+            self._execute_task(task)
+
+    def _execute_task(self, task):
+        """Execute a single ClickUp task immediately."""
         skill_map = self.config.clickup.skill_map
+        mapping = skill_map.get(task.task_type, {})
+        tool_name = mapping.get("tool", "")
+        if not tool_name:
+            log.warning("No tool in skill_map for type '%s'", task.task_type)
+            return
 
-        # Build state object
+        task_id = task.id
+        kv_key = f"clickup:task:{task_id}:state"
+        now = datetime.now(UTC).isoformat()
+        client = self._get_clickup_client()
+
+        # Build state object — starts at "executing"
         state = {
-            "state": "discovered",
-            "clickup_task_id": task.id,
+            "state": "executing",
+            "clickup_task_id": task_id,
             "clickup_task_name": task.name,
             "task_type": task.task_type,
-            "skill_name": None,
+            "skill_name": tool_name,
             "discovered_at": now,
-            "started_at": None,
+            "started_at": now,
             "completed_at": None,
             "error": None,
             "deliverable_paths": [],
             "custom_fields": task.custom_fields,
         }
 
-        # Try to map task type to a skill
-        mapping = skill_map.get(task.task_type)
-        if not mapping:
-            state["state"] = "unmapped"
-            self.db.kv_set(f"clickup:task:{task.id}:state", json.dumps(state))
-            active_ids.add(task.id)
-            self._notify(
-                f"New ClickUp task discovered but no skill mapping found.\n"
-                f"Task: **{task.name}** (Type: {task.task_type or 'none'})\n"
-                f"Configure a skill_map entry in config.yaml to handle this task type."
-            )
-            log.info("Unmapped ClickUp task: %s (type=%s)", task.name, task.task_type)
-            return
-
-        tool_name = mapping.get("tool", "")
-        auto_execute = mapping.get("auto_execute", self.config.clickup.default_auto_execute)
-        state["skill_name"] = tool_name
-
-        if auto_execute:
-            state["state"] = "approved"
-            self.db.kv_set(f"clickup:task:{task.id}:state", json.dumps(state))
-            active_ids.add(task.id)
-            self._notify(
-                f"New ClickUp task auto-approved for execution.\n"
-                f"Task: **{task.name}** → Skill: `{tool_name}`"
-            )
-            log.info("Auto-approved ClickUp task: %s → %s", task.name, tool_name)
-        else:
-            state["state"] = "awaiting_approval"
-            self.db.kv_set(f"clickup:task:{task.id}:state", json.dumps(state))
-            active_ids.add(task.id)
-            self._notify(
-                f"New ClickUp task needs your approval.\n"
-                f"Task: **{task.name}** → Skill: `{tool_name}`\n"
-                f'Use `clickup_approve_task("{task.id}")` to approve or '
-                f'`clickup_decline_task("{task.id}")` to decline.'
-            )
-            log.info("ClickUp task awaiting approval: %s → %s", task.name, tool_name)
-
-    def _execute_approved_tasks(self):
-        """Scan for approved tasks and execute them."""
-        pairs = self.db.kv_scan("clickup:task:")
-        for key, value in pairs:
-            if not key.endswith(":state"):
-                continue
-            try:
-                state = json.loads(value)
-            except json.JSONDecodeError:
-                continue
-
-            if state.get("state") != "approved":
-                continue
-
-            self._execute_clickup_task(state, key)
-
-    def _execute_clickup_task(self, state: dict, kv_key: str):
-        """Execute a single approved ClickUp task."""
-        task_id = state["clickup_task_id"]
-        task_name = state["clickup_task_name"]
-        skill_name = state["skill_name"]
-        now = datetime.now(UTC).isoformat()
-
-        log.info("Executing ClickUp task: %s → %s", task_name, skill_name)
-
-        # Update state to executing
-        state["state"] = "executing"
-        state["started_at"] = now
+        # Move to "in progress" on ClickUp immediately
+        client.update_task_status(task_id, self.config.clickup.in_progress_status)
         self.db.kv_set(kv_key, json.dumps(state))
 
-        client = self._get_clickup_client()
+        log.info("Executing ClickUp task: %s → %s", task.name, tool_name)
+        self._notify(
+            f"Executing ClickUp task: **{task.name}** → Skill: `{tool_name}`"
+        )
 
         try:
             # Build tool arguments from field mapping
             args = self._build_tool_args(state)
-
-            # Pass clickup_task_id so the tool can handle its own ClickUp sync
-            # (status updates, comments, attachments) if it supports it.
             args["clickup_task_id"] = task_id
 
             # Execute the skill via the tool registry
             if hasattr(self.agent, "_tools") and self.agent._tools:
-                result = self.agent._tools.execute(skill_name, args)
+                result = self.agent._tools.execute(tool_name, args)
             else:
                 result = self.agent.execute_task(
-                    f"Execute the '{skill_name}' tool for ClickUp task '{task_name}'. "
+                    f"Execute the '{tool_name}' tool for ClickUp task '{task.name}'. "
                     f"Task description: {state.get('custom_fields', {})}"
                 )
 
@@ -341,17 +357,11 @@ class Scheduler:
             tool_handled_sync = "## ClickUp Sync" in result
 
             if tool_handled_sync:
-                # Tool did its own status updates, comments, and attachments.
-                # Just update the kv_store state.
                 state["state"] = "completed"
                 state["completed_at"] = datetime.now(UTC).isoformat()
                 self.db.kv_set(kv_key, json.dumps(state))
             else:
-                # Tool doesn't handle sync — scheduler does it (fallback path).
-                # Set status to "in progress" (tool didn't do it)
-                client.update_task_status(task_id, self.config.clickup.in_progress_status)
-
-                # Extract and upload any docx deliverables
+                # Scheduler handles sync (fallback path)
                 docx_paths = _extract_docx_paths(result)
                 state["deliverable_paths"] = docx_paths
                 uploaded_count = 0
@@ -361,46 +371,45 @@ class Scheduler:
                     else:
                         log.warning("Failed to upload %s for task %s", path, task_id)
 
-                # Success
                 state["state"] = "completed"
                 state["completed_at"] = datetime.now(UTC).isoformat()
                 self.db.kv_set(kv_key, json.dumps(state))
 
-                # Update ClickUp
                 client.update_task_status(task_id, self.config.clickup.review_status)
                 attach_note = (
                     f"\n📎 {uploaded_count} file(s) attached." if uploaded_count else ""
                 )
                 comment = (
                     f"✅ CheddahBot completed this task.\n\n"
-                    f"Skill: {skill_name}\n"
+                    f"Skill: {tool_name}\n"
                     f"Result:\n{result[:3000]}{attach_note}"
                 )
                 client.add_comment(task_id, comment)
 
             self._notify(
-                f"ClickUp task completed: **{task_name}**\n"
-                f"Skill: `{skill_name}` | Status set to '{self.config.clickup.review_status}'"
+                f"ClickUp task completed: **{task.name}**\n"
+                f"Skill: `{tool_name}` | Status set to '{self.config.clickup.review_status}'"
             )
-            log.info("ClickUp task completed: %s", task_name)
+            log.info("ClickUp task completed: %s", task.name)
 
         except Exception as e:
-            # Failure
+            # Failure — move back to "to do" on ClickUp
             state["state"] = "failed"
             state["error"] = str(e)
             state["completed_at"] = datetime.now(UTC).isoformat()
             self.db.kv_set(kv_key, json.dumps(state))
 
-            # Comment the error on ClickUp
             client.add_comment(
                 task_id, f"❌ CheddahBot failed to complete this task.\n\nError: {str(e)[:2000]}"
             )
+            # Move back to "to do" so it can be retried after reset
+            client.update_task_status(task_id, "to do")
 
             self._notify(
-                f"ClickUp task failed: **{task_name}**\n"
-                f"Skill: `{skill_name}` | Error: {str(e)[:200]}"
+                f"ClickUp task failed: **{task.name}**\n"
+                f"Skill: `{tool_name}` | Error: {str(e)[:200]}"
             )
-            log.error("ClickUp task failed: %s — %s", task_name, e)
+            log.error("ClickUp task failed: %s — %s", task.name, e)
 
     def _build_tool_args(self, state: dict) -> dict:
         """Build tool arguments from ClickUp task fields using the field mapping."""
@@ -420,3 +429,195 @@ class Scheduler:
                 args[tool_param] = state.get("custom_fields", {}).get(source, "")
 
         return args
+
+    # ── Folder Watcher ──
+
+    def _folder_watch_loop(self):
+        """Poll the watch folder for new .xlsx files on a regular interval."""
+        interval = self.config.link_building.watch_interval_minutes * 60
+
+        # Wait before first scan to let other systems initialize
+        self._stop_event.wait(60)
+
+        while not self._stop_event.is_set():
+            try:
+                self._scan_watch_folder()
+            except Exception as e:
+                log.error("Folder watcher error: %s", e)
+            self._stop_event.wait(interval)
+
+    def _scan_watch_folder(self):
+        """Scan the watch folder for new .xlsx files and match to ClickUp tasks."""
+        watch_folder = Path(self.config.link_building.watch_folder)
+        if not watch_folder.exists():
+            log.warning("Watch folder does not exist: %s", watch_folder)
+            return
+
+        xlsx_files = sorted(watch_folder.glob("*.xlsx"))
+        if not xlsx_files:
+            log.debug("No .xlsx files in watch folder")
+            return
+
+        for xlsx_path in xlsx_files:
+            filename = xlsx_path.name
+            kv_key = f"linkbuilding:watched:{filename}"
+
+            # Skip already processed files
+            existing = self.db.kv_get(kv_key)
+            if existing:
+                try:
+                    state = json.loads(existing)
+                    if state.get("status") in ("completed", "processing", "failed"):
+                        continue
+                except json.JSONDecodeError:
+                    continue
+
+            log.info("Folder watcher: new .xlsx found: %s", filename)
+            self._process_watched_file(xlsx_path, kv_key)
+
+    def _process_watched_file(self, xlsx_path: Path, kv_key: str):
+        """Try to match a watched .xlsx file to a ClickUp task and run the pipeline."""
+        filename = xlsx_path.name
+        # Normalize filename stem for matching (e.g., "precision-cnc-machining" → "precision cnc machining")
+        stem = xlsx_path.stem.lower().replace("-", " ").replace("_", " ")
+        stem = re.sub(r"\s+", " ", stem).strip()
+
+        # Mark as processing
+        self.db.kv_set(kv_key, json.dumps({"status": "processing", "started_at": datetime.now(UTC).isoformat()}))
+
+        # Try to find matching ClickUp task
+        matched_task = None
+        if self.config.clickup.enabled:
+            matched_task = self._match_xlsx_to_clickup(stem)
+
+        if not matched_task:
+            log.warning("No ClickUp task match for '%s' — skipping", filename)
+            self.db.kv_set(kv_key, json.dumps({
+                "status": "unmatched",
+                "filename": filename,
+                "stem": stem,
+                "checked_at": datetime.now(UTC).isoformat(),
+            }))
+            self._notify(
+                f"Folder watcher: no ClickUp match for **{filename}**.\n"
+                f"Create a Link Building task with Keyword matching '{stem}' to enable auto-processing.",
+                category="linkbuilding",
+            )
+            return
+
+        # Extract tool args from matched task
+        task_id = matched_task.id
+        log.info("Matched '%s' to ClickUp task %s (%s)", filename, task_id, matched_task.name)
+        self._notify(
+            f"Folder watcher: matched **{filename}** to ClickUp task **{matched_task.name}**.\n"
+            f"Starting Cora Backlinks pipeline...",
+            category="linkbuilding",
+        )
+
+        # Build tool args from the matched task's custom fields
+        args = {
+            "xlsx_path": str(xlsx_path),
+            "project_name": matched_task.name,
+            "money_site_url": matched_task.custom_fields.get("IMSURL", ""),
+            "custom_anchors": matched_task.custom_fields.get("CustomAnchors", "") or "",
+            "cli_flags": matched_task.custom_fields.get("CLIFlags", "") or "",
+            "clickup_task_id": task_id,
+        }
+
+        # Parse branded_plus_ratio
+        bp_raw = matched_task.custom_fields.get("BrandedPlusRatio", "")
+        if bp_raw:
+            try:
+                args["branded_plus_ratio"] = float(bp_raw)
+            except (ValueError, TypeError):
+                pass
+
+        try:
+            # Execute via tool registry
+            if hasattr(self.agent, "_tools") and self.agent._tools:
+                result = self.agent._tools.execute("run_cora_backlinks", args)
+            else:
+                result = "Error: tool registry not available"
+
+            if "Error" in result and "## Step" not in result:
+                # Pipeline failed
+                self.db.kv_set(kv_key, json.dumps({
+                    "status": "failed",
+                    "filename": filename,
+                    "task_id": task_id,
+                    "error": result[:500],
+                    "failed_at": datetime.now(UTC).isoformat(),
+                }))
+                self._notify(
+                    f"Folder watcher: pipeline **failed** for **{filename}**.\n"
+                    f"Error: {result[:200]}",
+                    category="linkbuilding",
+                )
+            else:
+                # Success — move file to processed/
+                processed_dir = xlsx_path.parent / "processed"
+                processed_dir.mkdir(exist_ok=True)
+                dest = processed_dir / filename
+                try:
+                    shutil.move(str(xlsx_path), str(dest))
+                    log.info("Moved %s to %s", filename, dest)
+                except OSError as e:
+                    log.warning("Could not move %s to processed: %s", filename, e)
+
+                self.db.kv_set(kv_key, json.dumps({
+                    "status": "completed",
+                    "filename": filename,
+                    "task_id": task_id,
+                    "completed_at": datetime.now(UTC).isoformat(),
+                }))
+                self._notify(
+                    f"Folder watcher: pipeline **completed** for **{filename}**.\n"
+                    f"ClickUp task: {matched_task.name}",
+                    category="linkbuilding",
+                )
+
+        except Exception as e:
+            log.error("Folder watcher pipeline error for %s: %s", filename, e)
+            self.db.kv_set(kv_key, json.dumps({
+                "status": "failed",
+                "filename": filename,
+                "task_id": task_id,
+                "error": str(e)[:500],
+                "failed_at": datetime.now(UTC).isoformat(),
+            }))
+
+    def _match_xlsx_to_clickup(self, normalized_stem: str):
+        """Find a ClickUp Link Building task whose Keyword matches the file stem.
+
+        Returns the matched ClickUpTask or None.
+        """
+        from .tools.linkbuilding import _fuzzy_keyword_match, _normalize_for_match
+
+        client = self._get_clickup_client()
+        space_id = self.config.clickup.space_id
+        if not space_id:
+            return None
+
+        try:
+            tasks = client.get_tasks_from_space(space_id, statuses=["to do"])
+        except Exception as e:
+            log.warning("ClickUp query failed in _match_xlsx_to_clickup: %s", e)
+            return None
+
+        for task in tasks:
+            if task.task_type != "Link Building":
+                continue
+
+            lb_method = task.custom_fields.get("LB Method", "")
+            if lb_method and lb_method != "Cora Backlinks":
+                continue
+
+            keyword = task.custom_fields.get("Keyword", "")
+            if not keyword:
+                continue
+
+            keyword_norm = _normalize_for_match(str(keyword))
+            if _fuzzy_keyword_match(normalized_stem, keyword_norm):
+                return task
+
+        return None