diff --git a/cheddahbot/agent.py b/cheddahbot/agent.py
index 04ee48f..38904fa 100644
--- a/cheddahbot/agent.py
+++ b/cheddahbot/agent.py
@@ -369,6 +369,7 @@ class Agent:
         system_context: str = "",
         tools: str = "",
         model: str = "",
+        skip_permissions: bool = False,
     ) -> str:
         """Execute a task using the execution brain (Claude Code CLI).
 
@@ -378,6 +379,7 @@ class Agent:
         Args:
             tools: Override Claude Code tool list (e.g. "Bash,Read,WebSearch").
             model: Override the CLI model (e.g. "claude-sonnet-4.5").
+            skip_permissions: If True, run CLI with --dangerously-skip-permissions.
         """
         log.info("Execution brain task: %s", prompt[:100])
         kwargs: dict = {"system_prompt": system_context}
@@ -385,6 +387,8 @@ class Agent:
             kwargs["tools"] = tools
         if model:
             kwargs["model"] = model
+        if skip_permissions:
+            kwargs["skip_permissions"] = True
         result = self.llm.execute(prompt, **kwargs)
 
         # Log to daily memory
diff --git a/cheddahbot/config.py b/cheddahbot/config.py
index 647aec4..a04840a 100644
--- a/cheddahbot/config.py
+++ b/cheddahbot/config.py
@@ -95,6 +95,15 @@ class ApiBudgetConfig:
     alert_threshold: float = 0.8  # alert at 80% of limit
 
 
+@dataclass
+class ContentConfig:
+    cora_inbox: str = ""  # e.g. "Z:/content-cora-inbox"
+    outline_dir: str = ""  # e.g. "Z:/content-outlines"
+    company_capabilities_default: str = (
+        "All certifications and licenses need to be verified on the company's website."
+    )
+
+
 @dataclass
 class AgentConfig:
     """Per-agent configuration for multi-agent support."""
@@ -126,6 +135,7 @@ class Config:
     link_building: LinkBuildingConfig = field(default_factory=LinkBuildingConfig)
     autocora: AutoCoraConfig = field(default_factory=AutoCoraConfig)
     api_budget: ApiBudgetConfig = field(default_factory=ApiBudgetConfig)
+    content: ContentConfig = field(default_factory=ContentConfig)
     agents: list[AgentConfig] = field(default_factory=lambda: [AgentConfig()])
 
     # Derived paths
@@ -185,6 +195,10 @@ def load_config() -> Config:
             for k, v in data["api_budget"].items():
                 if hasattr(cfg.api_budget, k):
                     setattr(cfg.api_budget, k, v)
+        if "content" in data and isinstance(data["content"], dict):
+            for k, v in data["content"].items():
+                if hasattr(cfg.content, k):
+                    setattr(cfg.content, k, v)
 
         # Multi-agent configs
         if "agents" in data and isinstance(data["agents"], list):
diff --git a/cheddahbot/llm.py b/cheddahbot/llm.py
index 046e271..747a4f0 100644
--- a/cheddahbot/llm.py
+++ b/cheddahbot/llm.py
@@ -156,6 +156,7 @@ class LLMAdapter:
         working_dir: str | None = None,
         tools: str = "Bash,Read,Edit,Write,Glob,Grep",
         model: str | None = None,
+        skip_permissions: bool = False,
     ) -> str:
         """Execution brain: calls Claude Code CLI with full tool access.
 
@@ -165,6 +166,8 @@ class LLMAdapter:
         Args:
             tools: Comma-separated Claude Code tool names (default: standard set).
             model: Override the CLI model (e.g. "claude-sonnet-4.5").
+            skip_permissions: If True, append --dangerously-skip-permissions to
+                the CLI invocation (used for automated pipelines).
         """
         claude_bin = shutil.which("claude")
         if not claude_bin:
@@ -188,6 +191,8 @@ class LLMAdapter:
             cmd.extend(["--model", model])
         if system_prompt:
             cmd.extend(["--system-prompt", system_prompt])
+        if skip_permissions:
+            cmd.append("--dangerously-skip-permissions")
 
         log.debug("Execution brain cmd: %s", " ".join(cmd[:6]) + "...")
 
@@ -355,9 +360,14 @@ class LLMAdapter:
 
             except Exception as e:
                 if not has_yielded and attempt < max_retries and _is_retryable_error(e):
-                    wait = 2 ** attempt
-                    log.warning("Retryable LLM error (attempt %d/%d), retrying in %ds: %s",
-                                attempt + 1, max_retries + 1, wait, e)
+                    wait = 2**attempt
+                    log.warning(
+                        "Retryable LLM error (attempt %d/%d), retrying in %ds: %s",
+                        attempt + 1,
+                        max_retries + 1,
+                        wait,
+                        e,
+                    )
                     time.sleep(wait)
                     continue
                 yield {"type": "text", "content": _friendly_error(e, self.provider)}
diff --git a/cheddahbot/tools/content_creation.py b/cheddahbot/tools/content_creation.py
new file mode 100644
index 0000000..ba0a27c
--- /dev/null
+++ b/cheddahbot/tools/content_creation.py
@@ -0,0 +1,620 @@
+"""Two-phase content creation pipeline tool.
+
+Phase 1: Research competitors + generate outline → save → stop for human review.
+Phase 2: Human approves/edits outline → tool picks it up → writes full content.
+
+The content-researcher skill in the execution brain is triggered by keywords like
+"service page", "content optimization", "SEO content", etc.
+"""
+
+from __future__ import annotations
+
+import json
+import logging
+import re
+from datetime import UTC, datetime
+from pathlib import Path
+
+from . import tool
+
+log = logging.getLogger(__name__)
+
+_ROOT_DIR = Path(__file__).resolve().parent.parent.parent
+_DATA_DIR = _ROOT_DIR / "data"
+_LOCAL_CONTENT_DIR = _DATA_DIR / "generated" / "content"
+
+EXEC_TOOLS = "Bash,Read,Edit,Write,Glob,Grep,WebSearch,WebFetch"
+
+
+# ---------------------------------------------------------------------------
+# ClickUp helpers
+# ---------------------------------------------------------------------------
+
+
+def _get_clickup_client(ctx: dict | None):
+    """Create a ClickUpClient from tool context, or None if unavailable."""
+    if not ctx or not ctx.get("config") or not ctx["config"].clickup.enabled:
+        return None
+    try:
+        from ..clickup import ClickUpClient
+
+        config = ctx["config"]
+        return ClickUpClient(
+            api_token=config.clickup.api_token,
+            workspace_id=config.clickup.workspace_id,
+            task_type_field_name=config.clickup.task_type_field_name,
+        )
+    except Exception as e:
+        log.warning("Could not create ClickUp client: %s", e)
+        return None
+
+
+def _sync_clickup_start(ctx: dict | None, task_id: str) -> None:
+    """Move ClickUp task to 'automation underway'."""
+    if not task_id or not ctx:
+        return
+    client = _get_clickup_client(ctx)
+    if not client:
+        return
+    try:
+        config = ctx["config"]
+        client.update_task_status(task_id, config.clickup.automation_status)
+    except Exception as e:
+        log.warning("Failed to set ClickUp start status for %s: %s", task_id, e)
+    finally:
+        client.close()
+
+
+def _sync_clickup_outline_ready(ctx: dict | None, task_id: str, outline_path: str) -> None:
+    """Post outline comment and move ClickUp task to 'outline review'."""
+    if not task_id or not ctx:
+        return
+    client = _get_clickup_client(ctx)
+    if not client:
+        return
+    try:
+        client.add_comment(
+            task_id,
+            f"📝 CheddahBot generated a content outline.\n\n"
+            f"Outline saved to: `{outline_path}`\n\n"
+            f"Please review and edit the outline, then move this task to "
+            f"**outline approved** to trigger the full content write.",
+        )
+        client.update_task_status(task_id, "outline review")
+    except Exception as e:
+        log.warning("Failed to sync outline-ready for %s: %s", task_id, e)
+    finally:
+        client.close()
+
+
+def _sync_clickup_complete(ctx: dict | None, task_id: str, content_path: str) -> None:
+    """Post completion comment and move ClickUp task to 'internal review'."""
+    if not task_id or not ctx:
+        return
+    client = _get_clickup_client(ctx)
+    if not client:
+        return
+    try:
+        config = ctx["config"]
+        client.add_comment(
+            task_id,
+            f"✅ CheddahBot completed the content.\n\n"
+            f"Final content saved to: `{content_path}`\n\n"
+            f"Ready for internal review.",
+        )
+        client.update_task_status(task_id, config.clickup.review_status)
+    except Exception as e:
+        log.warning("Failed to sync completion for %s: %s", task_id, e)
+    finally:
+        client.close()
+
+
+def _sync_clickup_fail(ctx: dict | None, task_id: str, error: str) -> None:
+    """Post error comment and move ClickUp task to 'error'."""
+    if not task_id or not ctx:
+        return
+    client = _get_clickup_client(ctx)
+    if not client:
+        return
+    try:
+        config = ctx["config"]
+        client.add_comment(
+            task_id,
+            f"❌ CheddahBot failed during content creation.\n\nError: {error[:2000]}",
+        )
+        client.update_task_status(task_id, config.clickup.error_status)
+    except Exception as e:
+        log.warning("Failed to sync failure for %s: %s", task_id, e)
+    finally:
+        client.close()
+
+
+# ---------------------------------------------------------------------------
+# Helpers
+# ---------------------------------------------------------------------------
+
+
+def _slugify(text: str) -> str:
+    """Turn text into a filesystem-safe slug."""
+    text = text.lower().strip()
+    text = re.sub(r"[^\w\s-]", "", text)
+    text = re.sub(r"[\s_]+", "-", text)
+    return text[:80].strip("-")
+
+
+def _find_cora_report(keyword: str, cora_inbox: str) -> str:
+    """Fuzzy-match a Cora .xlsx report by keyword.
+
+    Match priority: exact filename match > substring > word overlap.
+    Skips Office temp files (~$...).
+    Returns the path string, or "" if not found.
+    """
+    if not cora_inbox or not keyword:
+        return ""
+    inbox = Path(cora_inbox)
+    if not inbox.exists():
+        return ""
+
+    xlsx_files = [f for f in inbox.glob("*.xlsx") if not f.name.startswith("~$")]
+    if not xlsx_files:
+        return ""
+
+    keyword_lower = keyword.lower().strip()
+    keyword_words = set(keyword_lower.split())
+
+    # Pass 1: exact stem match
+    for f in xlsx_files:
+        if f.stem.lower().strip() == keyword_lower:
+            return str(f)
+
+    # Pass 2: keyword is substring of filename (or vice versa)
+    for f in xlsx_files:
+        stem = f.stem.lower().strip()
+        if keyword_lower in stem or stem in keyword_lower:
+            return str(f)
+
+    # Pass 3: word overlap (at least half the keyword words)
+    best_match = ""
+    best_overlap = 0
+    for f in xlsx_files:
+        stem_words = set(f.stem.lower().replace("-", " ").replace("_", " ").split())
+        overlap = len(keyword_words & stem_words)
+        if overlap > best_overlap and overlap >= max(1, len(keyword_words) // 2):
+            best_overlap = overlap
+            best_match = str(f)
+
+    return best_match
+
+
+def _save_content(content: str, keyword: str, filename: str, config) -> str:
+    """Save content to the outline directory (network path with local fallback).
+
+    Returns the actual path used.
+    """
+    slug = _slugify(keyword)
+    if not slug:
+        slug = "unknown"
+
+    # Try primary (network) path
+    if config.content.outline_dir:
+        primary = Path(config.content.outline_dir) / slug
+        try:
+            primary.mkdir(parents=True, exist_ok=True)
+            out_path = primary / filename
+            out_path.write_text(content, encoding="utf-8")
+            return str(out_path)
+        except OSError as e:
+            log.warning("Network path unavailable (%s), falling back to local: %s", primary, e)
+
+    # Fallback to local
+    local = _LOCAL_CONTENT_DIR / slug
+    local.mkdir(parents=True, exist_ok=True)
+    out_path = local / filename
+    out_path.write_text(content, encoding="utf-8")
+    return str(out_path)
+
+
+# ---------------------------------------------------------------------------
+# Prompt builders
+# ---------------------------------------------------------------------------
+
+
+def _build_phase1_prompt(
+    url: str,
+    keyword: str,
+    content_type: str,
+    cora_path: str,
+    capabilities_default: str,
+) -> str:
+    """Build the Phase 1 prompt that triggers the content-researcher skill."""
+    parts = [
+        f"Research, outline, and draft an optimized {content_type} for {url} "
+        f"targeting keyword '{keyword}'. This is an SEO content optimization project.",
+    ]
+    if cora_path:
+        parts.append(
+            f"\nA Cora SEO report is available at: {cora_path}\n"
+            f"Read this report to extract keyword targets, entity requirements, "
+            f"and competitive analysis data."
+        )
+    if capabilities_default:
+        parts.append(
+            f'\nWhen asked about company capabilities, respond with: "{capabilities_default}"'
+        )
+    parts.append(
+        "\nDeliver the outline as a complete markdown document with sections, "
+        "headings, entity targets, and keyword placement notes."
+    )
+    return "\n".join(parts)
+
+
+def _build_phase2_prompt(
+    url: str,
+    keyword: str,
+    outline_text: str,
+    cora_path: str,
+) -> str:
+    """Build the Phase 2 prompt for writing full content from an approved outline."""
+    parts = [
+        f"Write full SEO-optimized content based on this approved outline for {url} "
+        f"targeting '{keyword}'. This is the content writing phase of a "
+        f"content optimization project.",
+        f"\n## Approved Outline\n\n{outline_text}",
+    ]
+    if cora_path:
+        parts.append(
+            f"\nThe Cora SEO report is at: {cora_path}\n"
+            f"Use it for keyword density targets and entity optimization."
+        )
+    parts.append(
+        "\nWrite publication-ready content following the outline structure. "
+        "Include all entity targets and keyword placements as noted in the outline."
+    )
+    return "\n".join(parts)
+
+
+# ---------------------------------------------------------------------------
+# Main tool
+# ---------------------------------------------------------------------------
+
+
+@tool(
+    "create_content",
+    "Two-phase SEO content creation: Phase 1 researches + outlines, Phase 2 writes "
+    "full content from the approved outline. Auto-detects phase from kv_store state.",
+    category="content",
+)
+def create_content(
+    url: str,
+    keyword: str,
+    content_type: str = "service page",
+    ctx: dict | None = None,
+) -> str:
+    """Create SEO content in two phases with human review between them.
+
+    Args:
+        url: Target page URL (e.g. "https://example.com/services/plumbing").
+        keyword: Primary target keyword (e.g. "plumbing services").
+        content_type: Type of content — "service page", "blog post", etc.
+    """
+    if not url or not keyword:
+        return "Error: Both 'url' and 'keyword' are required."
+    if not ctx or "agent" not in ctx:
+        return "Error: Tool context with agent is required."
+
+    agent = ctx["agent"]
+    config = ctx.get("config")
+    db = ctx.get("db")
+    task_id = ctx.get("clickup_task_id", "")
+    kv_key = f"clickup:task:{task_id}:state" if task_id else ""
+
+    # Determine phase from kv_store state
+    phase = 1
+    existing_state = {}
+    if kv_key and db:
+        raw = db.kv_get(kv_key)
+        if raw:
+            try:
+                existing_state = json.loads(raw)
+                if existing_state.get("state") == "outline_review":
+                    phase = 2
+            except json.JSONDecodeError:
+                pass
+
+    # Find Cora report
+    cora_inbox = config.content.cora_inbox if config else ""
+    cora_path = _find_cora_report(keyword, cora_inbox)
+    if cora_path:
+        log.info("Found Cora report for '%s': %s", keyword, cora_path)
+
+    capabilities_default = config.content.company_capabilities_default if config else ""
+
+    if phase == 1:
+        return _run_phase1(
+            agent=agent,
+            config=config,
+            db=db,
+            ctx=ctx,
+            task_id=task_id,
+            kv_key=kv_key,
+            url=url,
+            keyword=keyword,
+            content_type=content_type,
+            cora_path=cora_path,
+            capabilities_default=capabilities_default,
+        )
+    else:
+        return _run_phase2(
+            agent=agent,
+            config=config,
+            db=db,
+            ctx=ctx,
+            task_id=task_id,
+            kv_key=kv_key,
+            url=url,
+            keyword=keyword,
+            cora_path=cora_path,
+            existing_state=existing_state,
+        )
+
+
+# ---------------------------------------------------------------------------
+# Phase 1: Research + Outline
+# ---------------------------------------------------------------------------
+
+
+def _run_phase1(
+    *,
+    agent,
+    config,
+    db,
+    ctx,
+    task_id: str,
+    kv_key: str,
+    url: str,
+    keyword: str,
+    content_type: str,
+    cora_path: str,
+    capabilities_default: str,
+) -> str:
+    now = datetime.now(UTC).isoformat()
+
+    # ClickUp: move to automation underway
+    if task_id:
+        _sync_clickup_start(ctx, task_id)
+
+    prompt = _build_phase1_prompt(url, keyword, content_type, cora_path, capabilities_default)
+
+    log.info("Phase 1 — researching + outlining for '%s' (%s)", keyword, url)
+    try:
+        result = agent.execute_task(
+            prompt,
+            tools=EXEC_TOOLS,
+            skip_permissions=True,
+        )
+    except Exception as e:
+        error_msg = f"Phase 1 execution failed: {e}"
+        log.error(error_msg)
+        if task_id:
+            _update_kv_state(db, kv_key, "failed", error=str(e))
+            _sync_clickup_fail(ctx, task_id, str(e))
+        return f"Error: {error_msg}"
+
+    if result.startswith("Error:"):
+        if task_id:
+            _update_kv_state(db, kv_key, "failed", error=result)
+            _sync_clickup_fail(ctx, task_id, result)
+        return result
+
+    # Save the outline
+    outline_path = _save_content(result, keyword, "outline.md", config)
+    log.info("Outline saved to: %s", outline_path)
+
+    # Update kv_store
+    if kv_key and db:
+        state = {
+            "state": "outline_review",
+            "clickup_task_id": task_id,
+            "url": url,
+            "keyword": keyword,
+            "content_type": content_type,
+            "cora_path": cora_path,
+            "outline_path": outline_path,
+            "phase1_completed_at": now,
+            "completed_at": None,
+            "error": None,
+        }
+        db.kv_set(kv_key, json.dumps(state))
+
+    # ClickUp: move to outline review
+    if task_id:
+        _sync_clickup_outline_ready(ctx, task_id, outline_path)
+
+    return (
+        f"## Phase 1 Complete — Outline Ready for Review\n\n"
+        f"**Keyword:** {keyword}\n"
+        f"**URL:** {url}\n"
+        f"**Outline saved to:** `{outline_path}`\n\n"
+        f"Please review and edit the outline. When ready, move the ClickUp task "
+        f"to **outline approved** to trigger Phase 2 (full content writing).\n\n"
+        f"---\n\n{result}\n\n"
+        f"## ClickUp Sync\nPhase 1 complete. Status: outline review."
+    )
+
+
+# ---------------------------------------------------------------------------
+# Phase 2: Write Full Content
+# ---------------------------------------------------------------------------
+
+
+def _run_phase2(
+    *,
+    agent,
+    config,
+    db,
+    ctx,
+    task_id: str,
+    kv_key: str,
+    url: str,
+    keyword: str,
+    cora_path: str,
+    existing_state: dict,
+) -> str:
+    # Read the (possibly edited) outline
+    outline_path = existing_state.get("outline_path", "")
+    outline_text = ""
+    if outline_path:
+        try:
+            outline_text = Path(outline_path).read_text(encoding="utf-8")
+        except OSError as e:
+            log.warning("Could not read outline at %s: %s", outline_path, e)
+
+    if not outline_text:
+        return (
+            "Error: Could not read the outline file. "
+            f"Expected at: {outline_path or '(no path saved)'}"
+        )
+
+    # Use saved cora_path from state if we don't have one now
+    if not cora_path:
+        cora_path = existing_state.get("cora_path", "")
+
+    # ClickUp: move to automation underway
+    if task_id:
+        _sync_clickup_start(ctx, task_id)
+
+    prompt = _build_phase2_prompt(url, keyword, outline_text, cora_path)
+
+    log.info("Phase 2 — writing full content for '%s' (%s)", keyword, url)
+    try:
+        result = agent.execute_task(
+            prompt,
+            tools=EXEC_TOOLS,
+            skip_permissions=True,
+        )
+    except Exception as e:
+        error_msg = f"Phase 2 execution failed: {e}"
+        log.error(error_msg)
+        if task_id:
+            _update_kv_state(db, kv_key, "failed", error=str(e))
+            _sync_clickup_fail(ctx, task_id, str(e))
+        return f"Error: {error_msg}"
+
+    if result.startswith("Error:"):
+        if task_id:
+            _update_kv_state(db, kv_key, "failed", error=result)
+            _sync_clickup_fail(ctx, task_id, result)
+        return result
+
+    # Save final content
+    content_path = _save_content(result, keyword, "final-content.md", config)
+    log.info("Final content saved to: %s", content_path)
+
+    # Update kv_store
+    if kv_key and db:
+        now = datetime.now(UTC).isoformat()
+        state = existing_state.copy()
+        state["state"] = "completed"
+        state["content_path"] = content_path
+        state["completed_at"] = now
+        state["error"] = None
+        db.kv_set(kv_key, json.dumps(state))
+
+    # ClickUp: move to internal review
+    if task_id:
+        _sync_clickup_complete(ctx, task_id, content_path)
+
+    return (
+        f"## Phase 2 Complete — Content Written\n\n"
+        f"**Keyword:** {keyword}\n"
+        f"**URL:** {url}\n"
+        f"**Content saved to:** `{content_path}`\n\n"
+        f"---\n\n{result}\n\n"
+        f"## ClickUp Sync\nPhase 2 complete. Status: internal review."
+    )
+
+
+# ---------------------------------------------------------------------------
+# Continue content (chat-initiated Phase 2)
+# ---------------------------------------------------------------------------
+
+
+@tool(
+    "continue_content",
+    "Resume content creation for a keyword that has an approved outline. "
+    "Runs Phase 2 (full content writing) for a previously outlined keyword.",
+    category="content",
+)
+def continue_content(
+    keyword: str,
+    ctx: dict | None = None,
+) -> str:
+    """Resume content writing for a keyword with an approved outline.
+
+    Args:
+        keyword: The keyword to continue writing content for.
+    """
+    if not keyword:
+        return "Error: 'keyword' is required."
+    if not ctx or "agent" not in ctx or "db" not in ctx:
+        return "Error: Tool context with agent and db is required."
+
+    db = ctx["db"]
+    config = ctx.get("config")
+
+    # Scan kv_store for outline_review entries matching keyword
+    entries = db.kv_scan("clickup:task:")
+    keyword_lower = keyword.lower().strip()
+
+    for key, raw in entries:
+        try:
+            state = json.loads(raw)
+        except (json.JSONDecodeError, TypeError):
+            continue
+        if state.get("state") != "outline_review":
+            continue
+        if state.get("keyword", "").lower().strip() == keyword_lower:
+            # Found a matching entry — run Phase 2
+            task_id = state.get("clickup_task_id", "")
+            kv_key = key
+            url = state.get("url", "")
+            cora_path = state.get("cora_path", "")
+
+            return _run_phase2(
+                agent=ctx["agent"],
+                config=config,
+                db=db,
+                ctx=ctx,
+                task_id=task_id,
+                kv_key=kv_key,
+                url=url,
+                keyword=keyword,
+                cora_path=cora_path,
+                existing_state=state,
+            )
+
+    return (
+        f"No outline awaiting review found for keyword '{keyword}'. "
+        f"Use create_content to start Phase 1 first."
+    )
+
+
+# ---------------------------------------------------------------------------
+# KV state helper
+# ---------------------------------------------------------------------------
+
+
+def _update_kv_state(db, kv_key: str, state_val: str, error: str = "") -> None:
+    """Update kv_store state without losing existing data."""
+    if not db or not kv_key:
+        return
+    raw = db.kv_get(kv_key)
+    try:
+        state = json.loads(raw) if raw else {}
+    except json.JSONDecodeError:
+        state = {}
+    state["state"] = state_val
+    if error:
+        state["error"] = error[:2000]
+    state["completed_at"] = datetime.now(UTC).isoformat()
+    db.kv_set(kv_key, json.dumps(state))
diff --git a/config.yaml b/config.yaml
index fe03887..4fd9749 100644
--- a/config.yaml
+++ b/config.yaml
@@ -42,7 +42,7 @@ email:
 # ClickUp integration
 clickup:
   poll_interval_minutes: 20       # 3x per hour
-  poll_statuses: ["to do"]
+  poll_statuses: ["to do", "outline approved"]
   review_status: "internal review"
   in_progress_status: "in progress"
   automation_status: "automation underway"
@@ -58,6 +58,18 @@ clickup:
         company_name: "Customer"
         target_url: "IMSURL"
         branded_url: "SocialURL"
+    "On Page Optimization":
+      tool: "create_content"
+      auto_execute: true
+      field_mapping:
+        url: "IMSURL"
+        keyword: "Keyword"
+    "Content Creation":
+      tool: "create_content"
+      auto_execute: true
+      field_mapping:
+        url: "IMSURL"
+        keyword: "Keyword"
     "Link Building":
       tool: "run_link_building"
       auto_execute: false
@@ -88,6 +100,11 @@ autocora:
   error_status: "error"
   enabled: true
 
+# Content creation settings
+content:
+  cora_inbox: "Z:/content-cora-inbox"
+  outline_dir: "Z:/content-outlines"
+
 # Multi-agent configuration
 # Each agent gets its own personality, tool whitelist, and memory scope.
 # The first agent is the default. Omit this section for single-agent mode.
@@ -122,6 +139,11 @@ agents:
     tools: [run_link_building, run_cora_backlinks, blm_ingest_cora, blm_generate_batch, scan_cora_folder, submit_autocora_jobs, poll_autocora_results, delegate_task, remember, search_memory]
     memory_scope: ""
 
+  - name: content_creator
+    display_name: Content Creator
+    tools: [create_content, continue_content, delegate_task, remember, search_memory, web_search, web_fetch]
+    memory_scope: ""
+
   - name: planner
     display_name: Planner
     model: "x-ai/grok-4.1-fast"
diff --git a/tests/test_content_creation.py b/tests/test_content_creation.py
new file mode 100644
index 0000000..22c3811
--- /dev/null
+++ b/tests/test_content_creation.py
@@ -0,0 +1,471 @@
+"""Tests for the content creation pipeline tool."""
+
+from __future__ import annotations
+
+import json
+from pathlib import Path
+from unittest.mock import MagicMock, patch
+
+from cheddahbot.config import Config, ContentConfig
+from cheddahbot.tools.content_creation import (
+    _build_phase1_prompt,
+    _build_phase2_prompt,
+    _find_cora_report,
+    _save_content,
+    _slugify,
+    continue_content,
+    create_content,
+)
+
+# ---------------------------------------------------------------------------
+# _slugify
+# ---------------------------------------------------------------------------
+
+
+def test_slugify_basic():
+    assert _slugify("Plumbing Services") == "plumbing-services"
+
+
+def test_slugify_special_chars():
+    assert _slugify("AC Repair & Maintenance!") == "ac-repair-maintenance"
+
+
+def test_slugify_truncates():
+    long = "a" * 200
+    assert len(_slugify(long)) <= 80
+
+
+# ---------------------------------------------------------------------------
+# _build_phase1_prompt
+# ---------------------------------------------------------------------------
+
+
+class TestBuildPhase1Prompt:
+    def test_contains_trigger_keywords(self):
+        prompt = _build_phase1_prompt(
+            "https://example.com/plumbing",
+            "plumbing services",
+            "service page",
+            "",
+            "",
+        )
+        assert "SEO content optimization" in prompt
+        assert "plumbing services" in prompt
+        assert "service page" in prompt
+        assert "https://example.com/plumbing" in prompt
+
+    def test_includes_cora_path(self):
+        prompt = _build_phase1_prompt(
+            "https://example.com",
+            "keyword",
+            "blog post",
+            "Z:/cora/report.xlsx",
+            "",
+        )
+        assert "Z:/cora/report.xlsx" in prompt
+        assert "Cora SEO report" in prompt
+
+    def test_includes_capabilities_default(self):
+        default = "Verify on website."
+        prompt = _build_phase1_prompt(
+            "https://example.com",
+            "keyword",
+            "service page",
+            "",
+            default,
+        )
+        assert default in prompt
+        assert "company capabilities" in prompt
+
+    def test_no_cora_no_capabilities(self):
+        prompt = _build_phase1_prompt(
+            "https://example.com",
+            "keyword",
+            "service page",
+            "",
+            "",
+        )
+        assert "Cora SEO report" not in prompt
+        assert "company capabilities" not in prompt
+
+
+# ---------------------------------------------------------------------------
+# _build_phase2_prompt
+# ---------------------------------------------------------------------------
+
+
+class TestBuildPhase2Prompt:
+    def test_contains_outline(self):
+        outline = "## Section 1\nContent here."
+        prompt = _build_phase2_prompt(
+            "https://example.com",
+            "plumbing",
+            outline,
+            "",
+        )
+        assert outline in prompt
+        assert "content writing phase" in prompt
+        assert "plumbing" in prompt
+
+    def test_includes_cora_path(self):
+        prompt = _build_phase2_prompt(
+            "https://example.com",
+            "keyword",
+            "outline text",
+            "Z:/cora/report.xlsx",
+        )
+        assert "Z:/cora/report.xlsx" in prompt
+
+    def test_no_cora(self):
+        prompt = _build_phase2_prompt(
+            "https://example.com",
+            "keyword",
+            "outline text",
+            "",
+        )
+        assert "Cora SEO report" not in prompt
+
+
+# ---------------------------------------------------------------------------
+# _find_cora_report
+# ---------------------------------------------------------------------------
+
+
+class TestFindCoraReport:
+    def test_empty_inbox(self, tmp_path):
+        assert _find_cora_report("keyword", str(tmp_path)) == ""
+
+    def test_nonexistent_path(self):
+        assert _find_cora_report("keyword", "/nonexistent/path") == ""
+
+    def test_empty_keyword(self, tmp_path):
+        assert _find_cora_report("", str(tmp_path)) == ""
+
+    def test_exact_match(self, tmp_path):
+        report = tmp_path / "plumbing services.xlsx"
+        report.touch()
+        result = _find_cora_report("plumbing services", str(tmp_path))
+        assert result == str(report)
+
+    def test_substring_match(self, tmp_path):
+        report = tmp_path / "plumbing-services-city.xlsx"
+        report.touch()
+        result = _find_cora_report("plumbing services", str(tmp_path))
+        # "plumbing services" is a substring of "plumbing-services-city"
+        assert result == str(report)
+
+    def test_word_overlap(self, tmp_path):
+        report = tmp_path / "residential-plumbing-repair.xlsx"
+        report.touch()
+        result = _find_cora_report("plumbing repair", str(tmp_path))
+        assert result == str(report)
+
+    def test_skips_temp_files(self, tmp_path):
+        (tmp_path / "~$report.xlsx").touch()
+        (tmp_path / "actual-report.xlsx").touch()
+        result = _find_cora_report("actual report", str(tmp_path))
+        assert "~$" not in result
+        assert "actual-report" in result
+
+    def test_no_match(self, tmp_path):
+        (tmp_path / "completely-unrelated.xlsx").touch()
+        result = _find_cora_report("plumbing services", str(tmp_path))
+        assert result == ""
+
+
+# ---------------------------------------------------------------------------
+# _save_content
+# ---------------------------------------------------------------------------
+
+
+class TestSaveContent:
+    def _make_config(self, outline_dir: str = "") -> Config:
+        cfg = Config()
+        cfg.content = ContentConfig(outline_dir=outline_dir)
+        return cfg
+
+    def test_saves_to_primary_path(self, tmp_path):
+        cfg = self._make_config(str(tmp_path / "outlines"))
+        path = _save_content("# Outline", "plumbing services", "outline.md", cfg)
+        assert "outlines" in path
+        assert Path(path).read_text(encoding="utf-8") == "# Outline"
+
+    def test_falls_back_to_local(self, tmp_path):
+        # Point to an invalid network path
+        cfg = self._make_config("\\\\nonexistent\\share\\outlines")
+        with patch(
+            "cheddahbot.tools.content_creation._LOCAL_CONTENT_DIR",
+            tmp_path / "local",
+        ):
+            path = _save_content("# Outline", "plumbing", "outline.md", cfg)
+            assert str(tmp_path / "local") in path
+            assert Path(path).read_text(encoding="utf-8") == "# Outline"
+
+    def test_empty_outline_dir_uses_local(self, tmp_path):
+        cfg = self._make_config("")
+        with patch(
+            "cheddahbot.tools.content_creation._LOCAL_CONTENT_DIR",
+            tmp_path / "local",
+        ):
+            path = _save_content("content", "keyword", "outline.md", cfg)
+            assert str(tmp_path / "local") in path
+
+
+# ---------------------------------------------------------------------------
+# create_content — Phase 1
+# ---------------------------------------------------------------------------
+
+
+class TestCreateContentPhase1:
+    def _make_ctx(self, tmp_db, tmp_path):
+        cfg = Config()
+        cfg.content = ContentConfig(outline_dir=str(tmp_path / "outlines"))
+        agent = MagicMock()
+        agent.execute_task.return_value = "## Generated Outline\nSection 1..."
+        return {
+            "agent": agent,
+            "config": cfg,
+            "db": tmp_db,
+            "clickup_task_id": "task123",
+        }
+
+    def test_requires_url_and_keyword(self, tmp_db):
+        ctx = {"agent": MagicMock(), "config": Config(), "db": tmp_db}
+        assert create_content(url="", keyword="test", ctx=ctx).startswith("Error:")
+        assert create_content(url="http://x", keyword="", ctx=ctx).startswith("Error:")
+
+    def test_requires_context(self):
+        assert create_content(url="http://x", keyword="kw", ctx=None).startswith("Error:")
+
+    def test_phase1_runs_without_prior_state(self, tmp_db, tmp_path):
+        ctx = self._make_ctx(tmp_db, tmp_path)
+        result = create_content(
+            url="https://example.com/services",
+            keyword="plumbing services",
+            ctx=ctx,
+        )
+        assert "Phase 1 Complete" in result
+        assert "outline" in result.lower()
+        ctx["agent"].execute_task.assert_called_once()
+        call_kwargs = ctx["agent"].execute_task.call_args
+        assert call_kwargs.kwargs.get("skip_permissions") is True
+
+    def test_phase1_saves_outline_file(self, tmp_db, tmp_path):
+        ctx = self._make_ctx(tmp_db, tmp_path)
+        create_content(
+            url="https://example.com",
+            keyword="plumbing services",
+            ctx=ctx,
+        )
+        # The outline should have been saved
+        outline_dir = tmp_path / "outlines" / "plumbing-services"
+        assert outline_dir.exists()
+        saved = (outline_dir / "outline.md").read_text(encoding="utf-8")
+        assert saved == "## Generated Outline\nSection 1..."
+
+    def test_phase1_sets_kv_state(self, tmp_db, tmp_path):
+        ctx = self._make_ctx(tmp_db, tmp_path)
+        create_content(
+            url="https://example.com",
+            keyword="plumbing services",
+            ctx=ctx,
+        )
+        raw = tmp_db.kv_get("clickup:task:task123:state")
+        assert raw is not None
+        state = json.loads(raw)
+        assert state["state"] == "outline_review"
+        assert state["keyword"] == "plumbing services"
+        assert state["url"] == "https://example.com"
+        assert "outline_path" in state
+
+    def test_phase1_includes_clickup_sync_marker(self, tmp_db, tmp_path):
+        ctx = self._make_ctx(tmp_db, tmp_path)
+        result = create_content(
+            url="https://example.com",
+            keyword="test keyword",
+            ctx=ctx,
+        )
+        assert "## ClickUp Sync" in result
+
+
+# ---------------------------------------------------------------------------
+# create_content — Phase 2
+# ---------------------------------------------------------------------------
+
+
+class TestCreateContentPhase2:
+    def _setup_phase2(self, tmp_db, tmp_path):
+        """Set up an outline_review state and outline file, return ctx."""
+        cfg = Config()
+        cfg.content = ContentConfig(outline_dir=str(tmp_path / "outlines"))
+
+        # Create the outline file
+        outline_dir = tmp_path / "outlines" / "plumbing-services"
+        outline_dir.mkdir(parents=True)
+        outline_file = outline_dir / "outline.md"
+        outline_file.write_text("## Approved Outline\nSection content here.", encoding="utf-8")
+
+        # Set kv_store to outline_review
+        state = {
+            "state": "outline_review",
+            "clickup_task_id": "task456",
+            "url": "https://example.com/plumbing",
+            "keyword": "plumbing services",
+            "content_type": "service page",
+            "cora_path": "",
+            "outline_path": str(outline_file),
+        }
+        tmp_db.kv_set("clickup:task:task456:state", json.dumps(state))
+
+        agent = MagicMock()
+        agent.execute_task.return_value = "# Full Content\nParagraph..."
+        return {
+            "agent": agent,
+            "config": cfg,
+            "db": tmp_db,
+            "clickup_task_id": "task456",
+        }
+
+    def test_phase2_detects_outline_review_state(self, tmp_db, tmp_path):
+        ctx = self._setup_phase2(tmp_db, tmp_path)
+        result = create_content(
+            url="https://example.com/plumbing",
+            keyword="plumbing services",
+            ctx=ctx,
+        )
+        assert "Phase 2 Complete" in result
+
+    def test_phase2_reads_outline(self, tmp_db, tmp_path):
+        ctx = self._setup_phase2(tmp_db, tmp_path)
+        create_content(
+            url="https://example.com/plumbing",
+            keyword="plumbing services",
+            ctx=ctx,
+        )
+        call_args = ctx["agent"].execute_task.call_args
+        prompt = call_args.args[0] if call_args.args else call_args.kwargs.get("prompt", "")
+        assert "Approved Outline" in prompt
+
+    def test_phase2_saves_content_file(self, tmp_db, tmp_path):
+        ctx = self._setup_phase2(tmp_db, tmp_path)
+        create_content(
+            url="https://example.com/plumbing",
+            keyword="plumbing services",
+            ctx=ctx,
+        )
+        content_file = tmp_path / "outlines" / "plumbing-services" / "final-content.md"
+        assert content_file.exists()
+        assert content_file.read_text(encoding="utf-8") == "# Full Content\nParagraph..."
+
+    def test_phase2_sets_completed_state(self, tmp_db, tmp_path):
+        ctx = self._setup_phase2(tmp_db, tmp_path)
+        create_content(
+            url="https://example.com/plumbing",
+            keyword="plumbing services",
+            ctx=ctx,
+        )
+        raw = tmp_db.kv_get("clickup:task:task456:state")
+        state = json.loads(raw)
+        assert state["state"] == "completed"
+        assert "content_path" in state
+
+    def test_phase2_includes_clickup_sync_marker(self, tmp_db, tmp_path):
+        ctx = self._setup_phase2(tmp_db, tmp_path)
+        result = create_content(
+            url="https://example.com/plumbing",
+            keyword="plumbing services",
+            ctx=ctx,
+        )
+        assert "## ClickUp Sync" in result
+
+
+# ---------------------------------------------------------------------------
+# continue_content
+# ---------------------------------------------------------------------------
+
+
+class TestContinueContent:
+    def test_requires_keyword(self, tmp_db):
+        ctx = {"agent": MagicMock(), "db": tmp_db, "config": Config()}
+        assert continue_content(keyword="", ctx=ctx).startswith("Error:")
+
+    def test_no_matching_entry(self, tmp_db):
+        ctx = {"agent": MagicMock(), "db": tmp_db, "config": Config()}
+        result = continue_content(keyword="nonexistent", ctx=ctx)
+        assert "No outline awaiting review" in result
+
+    def test_finds_and_runs_phase2(self, tmp_db, tmp_path):
+        cfg = Config()
+        cfg.content = ContentConfig(outline_dir=str(tmp_path / "outlines"))
+
+        # Create outline file
+        outline_dir = tmp_path / "outlines" / "plumbing-services"
+        outline_dir.mkdir(parents=True)
+        outline_file = outline_dir / "outline.md"
+        outline_file.write_text("## Outline", encoding="utf-8")
+
+        # Set kv state
+        state = {
+            "state": "outline_review",
+            "clickup_task_id": "task789",
+            "url": "https://example.com",
+            "keyword": "plumbing services",
+            "outline_path": str(outline_file),
+            "cora_path": "",
+        }
+        tmp_db.kv_set("clickup:task:task789:state", json.dumps(state))
+
+        agent = MagicMock()
+        agent.execute_task.return_value = "# Full content"
+        ctx = {"agent": agent, "db": tmp_db, "config": cfg}
+        result = continue_content(keyword="plumbing services", ctx=ctx)
+        assert "Phase 2 Complete" in result
+
+
+# ---------------------------------------------------------------------------
+# Error propagation
+# ---------------------------------------------------------------------------
+
+
+class TestErrorPropagation:
+    def test_phase1_execution_error_sets_failed_state(self, tmp_db, tmp_path):
+        cfg = Config()
+        cfg.content = ContentConfig(outline_dir=str(tmp_path / "outlines"))
+        agent = MagicMock()
+        agent.execute_task.side_effect = RuntimeError("CLI crashed")
+        ctx = {
+            "agent": agent,
+            "config": cfg,
+            "db": tmp_db,
+            "clickup_task_id": "task_err",
+        }
+        result = create_content(
+            url="https://example.com",
+            keyword="test",
+            ctx=ctx,
+        )
+        assert "Error:" in result
+        raw = tmp_db.kv_get("clickup:task:task_err:state")
+        state = json.loads(raw)
+        assert state["state"] == "failed"
+
+    def test_phase1_error_return_sets_failed(self, tmp_db, tmp_path):
+        cfg = Config()
+        cfg.content = ContentConfig(outline_dir=str(tmp_path / "outlines"))
+        agent = MagicMock()
+        agent.execute_task.return_value = "Error: something went wrong"
+        ctx = {
+            "agent": agent,
+            "config": cfg,
+            "db": tmp_db,
+            "clickup_task_id": "task_err2",
+        }
+        result = create_content(
+            url="https://example.com",
+            keyword="test",
+            ctx=ctx,
+        )
+        assert result.startswith("Error:")
+        raw = tmp_db.kv_get("clickup:task:task_err2:state")
+        state = json.loads(raw)
+        assert state["state"] == "failed"