diff --git a/src/fabledassistant/services/tools.py b/src/fabledassistant/services/tools.py
index 8f06c78..3733e4d 100644
--- a/src/fabledassistant/services/tools.py
+++ b/src/fabledassistant/services/tools.py
@@ -2,7 +2,9 @@
 
 import asyncio
 import logging
+import re
 from datetime import date, datetime
+from difflib import SequenceMatcher
 
 from fabledassistant.services.caldav import (
     create_event,
@@ -67,6 +69,10 @@ _CORE_TOOLS = [
                         "type": "string",
                         "description": "Optional milestone title within the project to assign this task to",
                     },
+                    "confirmed": {
+                        "type": "boolean",
+                        "description": "Set to true only when the user has explicitly confirmed creation after being warned about a similar existing task.",
+                    },
                 },
                 "required": ["title"],
             },
@@ -97,6 +103,10 @@ _CORE_TOOLS = [
                         "type": "string",
                         "description": "Optional project name to assign this note to",
                     },
+                    "confirmed": {
+                        "type": "boolean",
+                        "description": "Set to true only when the user has explicitly confirmed creation after being warned about a similar existing note.",
+                    },
                 },
                 "required": ["title"],
             },
@@ -338,15 +348,16 @@ _CORE_TOOLS = [
         "type": "function",
         "function": {
             "name": "create_project",
-            "description": "Create a new project. Use when the user asks to create a project, initiative, or campaign to organize related tasks and notes.",
+            "description": "Create a new project. IMPORTANT: You MUST ask the user to confirm the project name and intent before calling this tool. Only call with confirmed=true after the user has explicitly approved creation.",
             "parameters": {
                 "type": "object",
                 "properties": {
                     "title": {"type": "string", "description": "Project title"},
                     "description": {"type": "string", "description": "Brief description"},
                     "goal": {"type": "string", "description": "The goal or desired outcome"},
+                    "confirmed": {"type": "boolean", "description": "Must be true — only set after the user has explicitly confirmed they want this project created."},
                 },
-                "required": ["title"],
+                "required": ["title", "confirmed"],
             },
         },
     },
@@ -402,15 +413,16 @@ _CORE_TOOLS = [
         "type": "function",
         "function": {
             "name": "create_milestone",
-            "description": "Create a new milestone inside a project for grouping and tracking related tasks.",
+            "description": "Create a new milestone inside a project. IMPORTANT: You MUST ask the user to confirm the milestone name and which project it belongs to before calling this tool. Only call with confirmed=true after the user has explicitly approved creation.",
             "parameters": {
                 "type": "object",
                 "properties": {
-                    "project": {"type": "string", "description": "Project title (will be created if not found)"},
+                    "project": {"type": "string", "description": "Project title"},
                     "title": {"type": "string", "description": "Milestone title"},
                     "description": {"type": "string", "description": "Optional description"},
+                    "confirmed": {"type": "boolean", "description": "Must be true — only set after the user has explicitly confirmed they want this milestone created."},
                 },
-                "required": ["project", "title"],
+                "required": ["project", "title", "confirmed"],
             },
         },
     },
@@ -710,6 +722,27 @@ def _parse_due_date(value: str | None) -> date | None:
         return None
 
 
+_PUNCT_RE = re.compile(r"[^\w\s]")
+
+
+def _fuzzy_title_match(title: str, candidates, threshold: float = 0.82):
+    """Return (best_match, ratio) if any candidate's title is similar enough to *title*.
+
+    Uses SequenceMatcher ratio, which handles insertions/deletions/substitutions.
+    A threshold of 0.82 catches near-duplicates like "Game Premise" / "Game Premise Notes"
+    while leaving clearly different titles alone.
+    Returns (None, 0.0) when no candidate meets the threshold.
+    """
+    needle = title.lower().strip()
+    best, best_r = None, 0.0
+    for c in candidates:
+        r = SequenceMatcher(None, needle, c.title.lower().strip()).ratio()
+        if r >= threshold and r > best_r:
+            best, best_r = c, r
+    return best, best_r
+
+
+
 async def execute_tool(user_id: int, tool_name: str, arguments: dict) -> dict:
     """Execute a tool call and return the result."""
     try:
@@ -742,6 +775,27 @@ async def execute_tool(user_id: int, tool_name: str, arguments: dict) -> dict:
                         return {"success": False, "error": f"Milestone '{milestone_name}' not found in project '{proj.title}'. Use list_milestones to see available milestones."}
                     pre_fields["milestone_id"] = ms.id
 
+            existing = await get_note_by_title(user_id, task_title)
+            if existing is not None:
+                item_type = "task" if existing.status is not None else "note"
+                return {"success": False, "error": f"A {item_type} titled '{task_title}' already exists (id: {existing.id}). Use update_note to modify it instead of creating a duplicate."}
+
+            clean_q = _PUNCT_RE.sub(" ", task_title).strip()
+            candidates, _ = await list_notes(user_id=user_id, q=clean_q, limit=20)
+            near, ratio = _fuzzy_title_match(task_title, candidates)
+            if near is not None:
+                item_type = "task" if near.status is not None else "note"
+                return {"success": False, "error": f"A {item_type} with a very similar title '{near.title}' already exists (id: {near.id}, similarity: {ratio:.0%}). Use update_note to modify it instead of creating a duplicate."}
+
+            if not arguments.get("confirmed"):
+                from fabledassistant.services.embeddings import semantic_search_notes as _ssn
+                sem_query = f"{task_title}\n{task_body}".strip()
+                sem_hits = await _ssn(user_id, sem_query, limit=3, threshold=0.87)
+                if sem_hits:
+                    best_score, best_note = sem_hits[0]
+                    item_type = "task" if best_note.status is not None else "note"
+                    return {"success": False, "requires_confirmation": True, "error": f"A {item_type} with very similar content exists: '{best_note.title}' (id: {best_note.id}, semantic similarity: {best_score:.0%}). Ask the user: 'An existing {item_type} covers very similar ground. Shall I still create a separate task titled \"{task_title}\"?' Then retry with confirmed=true if they agree."}
+
             note = await create_note(
                 user_id=user_id,
                 title=task_title,
@@ -799,6 +853,27 @@ async def execute_tool(user_id: int, tool_name: str, arguments: dict) -> dict:
                     return {"success": False, "error": f"Project '{project_name}' not found. Use list_projects to see available projects or create_project to create one."}
                 project_id = proj.id
 
+            existing = await get_note_by_title(user_id, note_title)
+            if existing is not None:
+                item_type = "task" if existing.status is not None else "note"
+                return {"success": False, "error": f"A {item_type} titled '{note_title}' already exists (id: {existing.id}). Use update_note to modify it instead of creating a duplicate."}
+
+            clean_q = _PUNCT_RE.sub(" ", note_title).strip()
+            candidates, _ = await list_notes(user_id=user_id, q=clean_q, limit=20)
+            near, ratio = _fuzzy_title_match(note_title, candidates)
+            if near is not None:
+                item_type = "task" if near.status is not None else "note"
+                return {"success": False, "error": f"A {item_type} with a very similar title '{near.title}' already exists (id: {near.id}, similarity: {ratio:.0%}). Use update_note to modify it instead of creating a duplicate."}
+
+            if not arguments.get("confirmed"):
+                from fabledassistant.services.embeddings import semantic_search_notes as _ssn
+                sem_query = f"{note_title}\n{note_body}".strip()
+                sem_hits = await _ssn(user_id, sem_query, limit=3, threshold=0.87)
+                if sem_hits:
+                    best_score, best_note = sem_hits[0]
+                    item_type = "task" if best_note.status is not None else "note"
+                    return {"success": False, "requires_confirmation": True, "error": f"A {item_type} with very similar content exists: '{best_note.title}' (id: {best_note.id}, semantic similarity: {best_score:.0%}). Ask the user: 'An existing {item_type} covers very similar ground. Shall I still create a separate note titled \"{note_title}\"?' Then retry with confirmed=true if they agree."}
+
             note = await create_note(
                 user_id=user_id,
                 title=note_title,
@@ -1191,8 +1266,11 @@ async def execute_tool(user_id: int, tool_name: str, arguments: dict) -> dict:
             from fabledassistant.services.projects import get_project_by_title as _gpbt, list_projects as _lp
             from fabledassistant.services.milestones import create_milestone as _cm, get_project_milestone_summary
             project_name = arguments.get("project", "")
+            ms_title_pre = arguments.get("title", "Untitled Milestone")
             if not project_name:
                 return {"success": False, "error": "project is required"}
+            if not arguments.get("confirmed"):
+                return {"success": False, "requires_confirmation": True, "error": f"Milestone creation requires explicit user confirmation. Ask the user: 'Shall I create a milestone titled \"{ms_title_pre}\" in project \"{project_name}\"?' Then retry with confirmed=true if they agree."}
             proj = await _gpbt(user_id, project_name)
             if proj is None:
                 all_p = await _lp(user_id)
@@ -1200,10 +1278,19 @@ async def execute_tool(user_id: int, tool_name: str, arguments: dict) -> dict:
                 proj = matches[0] if matches else None
             if proj is None:
                 return {"success": False, "error": f"Project '{project_name}' not found. Use list_projects to see available projects or create_project to create one."}
+            ms_title = ms_title_pre
+            from fabledassistant.services.milestones import get_milestone_by_title as _gmbt2, list_milestones as _lms
+            existing_ms = await _gmbt2(user_id, proj.id, ms_title)
+            if existing_ms is not None:
+                return {"success": False, "error": f"A milestone titled '{existing_ms.title}' already exists in '{proj.title}' (id: {existing_ms.id}). Use update_milestone to modify it instead."}
+            all_ms = await _lms(user_id, proj.id)
+            near_ms, ratio = _fuzzy_title_match(ms_title, all_ms)
+            if near_ms is not None:
+                return {"success": False, "error": f"A milestone with a very similar title '{near_ms.title}' already exists in '{proj.title}' (id: {near_ms.id}, similarity: {ratio:.0%}). Use update_milestone to modify it instead."}
             ms = await _cm(
                 user_id,
                 proj.id,
-                title=arguments.get("title", "Untitled Milestone"),
+                title=ms_title,
                 description=arguments.get("description"),
             )
             return {"success": True, "type": "milestone", "data": ms.to_dict()}
@@ -1253,10 +1340,20 @@ async def execute_tool(user_id: int, tool_name: str, arguments: dict) -> dict:
             }
 
         elif tool_name == "create_project":
-            from fabledassistant.services.projects import create_project as _create_project
+            from fabledassistant.services.projects import create_project as _create_project, get_project_by_title as _gpbt, list_projects as _lp
+            proj_title = arguments.get("title", "New Project")
+            if not arguments.get("confirmed"):
+                return {"success": False, "requires_confirmation": True, "error": f"Project creation requires explicit user confirmation. Ask the user: 'Shall I create a new project titled \"{proj_title}\"?' Then retry with confirmed=true if they agree."}
+            existing_proj = await _gpbt(user_id, proj_title)
+            if existing_proj is not None:
+                return {"success": False, "error": f"A project titled '{existing_proj.title}' already exists (id: {existing_proj.id}). Use update_project to modify it instead of creating a duplicate."}
+            all_projects = await _lp(user_id)
+            near_proj, ratio = _fuzzy_title_match(proj_title, all_projects)
+            if near_proj is not None:
+                return {"success": False, "error": f"A project with a very similar title '{near_proj.title}' already exists (id: {near_proj.id}, similarity: {ratio:.0%}). Use update_project to modify it instead of creating a duplicate."}
             project = await _create_project(
                 user_id,
-                title=arguments.get("title", "New Project"),
+                title=proj_title,
                 description=arguments.get("description", ""),
                 goal=arguments.get("goal", ""),
             )
diff --git a/summary.md b/summary.md
index 1f81c63..c2dde61 100644
--- a/summary.md
+++ b/summary.md
@@ -12,7 +12,7 @@
 >    Include file-level details in the commit body when the change is non-trivial.
 
 ## Last Updated
-2026-03-03 — Project/milestone association bug fixes (tasks route was silently dropping project_id/milestone_id); PATCH /api/notes endpoint; parent_title in task API response; milestone_id support in NoteEditorView + notes store; sub-tasks inherit milestone; list_notes OR query for project view; AppHeader redesigned (centered nav, gear dropdown for settings)
+2026-03-03 — Duplicate entry prevention in LLM tool pipeline: exact-title block, fuzzy-title block (SequenceMatcher ≥82%), semantic content check (≥87% cosine similarity via existing `semantic_search_notes`); `create_project`/`create_milestone` require explicit `confirmed:true`; `create_note`/`create_task` have optional `confirmed` for content-similarity soft-block; `create_project`/`create_milestone` also protected by exact+fuzzy title checks
 
 ## Project Overview
 Fabled Assistant is a self-hosted note-taking and task-tracking application with
@@ -612,7 +612,15 @@ When adding a new migration, follow these conventions:
   System prompt includes today's date for relative date resolution. Graceful degradation: models without
   tool support respond normally.
   Full tool suite:
-  - `create_task` / `create_note` — create new items
+  - `create_task` / `create_note` — create new items; protected by a three-layer duplicate guard:
+    1. **Exact title** (case-insensitive via `get_note_by_title`) → hard block, redirect to `update_note`
+    2. **Fuzzy title** (`SequenceMatcher` ≥82%; strips punctuation before word search for candidates) → hard block
+    3. **Semantic content** (`semantic_search_notes` threshold 0.87, graceful no-op if embedding model down) → soft block with `requires_confirmation:true`; model must ask user then retry with `confirmed:true`
+    Both tools have an optional `confirmed` parameter (not required by default — only needed when a content-similarity warning fires).
+  - `create_project` — always requires `confirmed:true` before creation (structural, must be intentional);
+    additionally guarded by exact + fuzzy title checks (≥82%) against existing projects
+  - `create_milestone` — always requires `confirmed:true`; additionally guarded by exact + fuzzy title
+    checks against existing milestones within the same project
   - `update_note` — edit note content (replace/append) AND update task fields: `status`, `priority`,
     `due_date`, `tags` (with `tag_mode`: replace/add/remove); finds by exact title first, falls back to fuzzy search
   - `delete_note` / `delete_task` — permanently delete (require user confirmation via confirm UI;
@@ -625,6 +633,7 @@ When adding a new migration, follow these conventions:
   - Full CalDAV suite: `create_event`, `list_events`, `search_events`, `update_event`, `delete_event`,
     `list_calendars`, `create_todo`, `list_todos`, `search_todos`, `update_todo`, `complete_todo`, `delete_todo`
     (`search_todos` keyword-filters the todo list — companion to `list_todos`)
+  - **Duplicate guard helpers** in `services/tools.py`: `_fuzzy_title_match(title, candidates, threshold=0.82)` uses `SequenceMatcher`; semantic check uses `semantic_search_notes` at threshold 0.87 (vs. 0.45 for RAG suggestions). `_PUNCT_RE` strips punctuation from title before word-search to avoid false-negative candidates (e.g. "Shackled - Game Premise" → "Shackled Game Premise" query).
 - **Streaming status transparency:** The backend emits `status` SSE events at each pipeline stage
   so the user always sees what's happening instead of a blank progress dot. Stages:
   (1) intent ack text streamed as a `chunk` event (tool responses — TTFT ~400ms) or