diff --git a/cogs/sentiment/__init__.py b/cogs/sentiment/__init__.py
index 48cb030..558068e 100644
--- a/cogs/sentiment/__init__.py
+++ b/cogs/sentiment/__init__.py
@@ -13,6 +13,7 @@ from cogs.sentiment.coherence import handle_coherence_alert
 from cogs.sentiment.log_utils import log_analysis
 from cogs.sentiment.state import flush_dirty_states
 from cogs.sentiment.topic_drift import handle_topic_drift
+from cogs.sentiment.unblock_nag import handle_unblock_nag, matches_unblock_nag
 
 logger = logging.getLogger("bcs.sentiment")
 
@@ -153,6 +154,12 @@ class SentimentCog(commands.Cog):
         if not message.content or not message.content.strip():
             return
 
+        # Check for unblock nagging (keyword-based, no LLM needed for detection)
+        if matches_unblock_nag(message.content):
+            asyncio.create_task(handle_unblock_nag(
+                self.bot, message, self._dirty_users,
+            ))
+
         # Buffer the message and start/reset debounce timer (per-channel)
         channel_id = message.channel.id
         if channel_id not in self._message_buffer:
diff --git a/cogs/sentiment/unblock_nag.py b/cogs/sentiment/unblock_nag.py
new file mode 100644
index 0000000..c3319b9
--- /dev/null
+++ b/cogs/sentiment/unblock_nag.py
@@ -0,0 +1,161 @@
+import asyncio
+import logging
+import random
+import re
+from collections import deque
+from pathlib import Path
+
+import discord
+
+from cogs.sentiment.log_utils import log_action
+from cogs.sentiment.state import save_user_state
+
+logger = logging.getLogger("bcs.sentiment")
+
+_PROMPTS_DIR = Path(__file__).resolve().parent.parent.parent / "prompts"
+_UNBLOCK_REDIRECT_PROMPT = (_PROMPTS_DIR / "unblock_redirect.txt").read_text(encoding="utf-8")
+
+# Regex: matches "unblock" as a whole word, case-insensitive
+UNBLOCK_PATTERN = re.compile(r"\bunblock(?:ed|ing|s)?\b", re.IGNORECASE)
+
+DEFAULT_UNBLOCK_REMINDS = [
+    "{username}, begging to be unblocked in chat is not the move. Take it up with an admin. 🙄",
+    "{username}, nobody's getting unblocked because you asked nicely in a gaming channel.",
+    "Hey {username}, the unblock button isn't in this chat. Just saying.",
+    "{username}, I admire the persistence but this isn't the unblock hotline.",
+    "{username}, that's between you and whoever blocked you. Chat isn't the appeals court.",
+]
+
+DEFAULT_UNBLOCK_NUDGES = [
+    "{username}, we've been over this. No amount of asking here is going to change anything. 🙄",
+    "{username}, I'm starting to think you enjoy being told no. Still not getting unblocked via chat.",
+    "{username}, at this point I could set a reminder for your next unblock request. Take it to an admin.",
+    "Babe. {username}. We've had this conversation {count} times. It's not happening here. 😭",
+    "{username}, I'm keeping a tally and you're at {count}. The answer is still the same.",
+]
+
+# Per-channel deque of recent LLM-generated messages (for variety)
+_recent_redirects: dict[int, deque] = {}
+
+
+def _get_recent_redirects(channel_id: int) -> list[str]:
+    if channel_id in _recent_redirects:
+        return list(_recent_redirects[channel_id])
+    return []
+
+
+def _record_redirect(channel_id: int, text: str):
+    if channel_id not in _recent_redirects:
+        _recent_redirects[channel_id] = deque(maxlen=5)
+    _recent_redirects[channel_id].append(text)
+
+
+def _strip_brackets(text: str) -> str:
+    """Strip leaked LLM metadata brackets."""
+    segments = re.split(r"^\s*\[[^\]]*\]\s*$", text, flags=re.MULTILINE)
+    segments = [s.strip() for s in segments if s.strip()]
+    return segments[-1] if segments else ""
+
+
+def matches_unblock_nag(content: str) -> bool:
+    """Check if a message contains unblock-related nagging."""
+    return bool(UNBLOCK_PATTERN.search(content))
+
+
+async def _generate_llm_redirect(
+    bot, message: discord.Message, count: int,
+) -> str | None:
+    """Ask the LLM chat model to generate an unblock-nag redirect."""
+    recent = _get_recent_redirects(message.channel.id)
+
+    user_prompt = (
+        f"Username: {message.author.display_name}\n"
+        f"Channel: #{getattr(message.channel, 'name', 'unknown')}\n"
+        f"Unblock nag count: {count}\n"
+        f"What they said: {message.content[:300]}"
+    )
+
+    messages = [{"role": "user", "content": user_prompt}]
+
+    effective_prompt = _UNBLOCK_REDIRECT_PROMPT
+    if recent:
+        avoid_block = "\n".join(f"- {r}" for r in recent)
+        effective_prompt += (
+            "\n\nIMPORTANT — you recently sent these redirects in the same channel. "
+            "Do NOT repeat any of these. Be completely different.\n"
+            + avoid_block
+        )
+
+    try:
+        response = await bot.llm_chat.chat(messages, effective_prompt)
+    except Exception:
+        logger.exception("LLM unblock redirect generation failed")
+        return None
+
+    if response:
+        response = _strip_brackets(response)
+
+    return response if response else None
+
+
+def _static_fallback(message: discord.Message, count: int) -> str:
+    """Pick a static template message as fallback."""
+    if count >= 2:
+        pool = DEFAULT_UNBLOCK_NUDGES
+    else:
+        pool = DEFAULT_UNBLOCK_REMINDS
+    return random.choice(pool).format(
+        username=message.author.display_name, count=count,
+    )
+
+
+async def handle_unblock_nag(
+    bot, message: discord.Message, dirty_users: set[int],
+):
+    """Handle a detected unblock-nagging message."""
+    config = bot.config.get("unblock_nag", {})
+    if not config.get("enabled", True):
+        return
+
+    dry_run = bot.config.get("monitoring", {}).get("dry_run", False)
+    if dry_run:
+        return
+
+    tracker = bot.drama_tracker
+    user_id = message.author.id
+    cooldown = config.get("remind_cooldown_minutes", 30)
+
+    if not tracker.can_unblock_remind(user_id, cooldown):
+        return
+
+    count = tracker.record_unblock_nag(user_id)
+    action_type = "unblock_nudge" if count >= 2 else "unblock_remind"
+
+    # Generate the redirect message
+    use_llm = config.get("use_llm", True)
+    redirect_text = None
+    if use_llm:
+        redirect_text = await _generate_llm_redirect(bot, message, count)
+
+    if redirect_text:
+        _record_redirect(message.channel.id, redirect_text)
+    else:
+        redirect_text = _static_fallback(message, count)
+
+    await message.channel.send(redirect_text)
+
+    await log_action(
+        message.guild,
+        f"**UNBLOCK {'NUDGE' if count >= 2 else 'REMIND'}** | {message.author.mention} | "
+        f"Nag count: {count}",
+    )
+
+    logger.info("Unblock %s for %s (count %d)", action_type.replace("unblock_", ""), message.author, count)
+
+    asyncio.create_task(bot.db.save_action(
+        guild_id=message.guild.id, user_id=user_id,
+        username=message.author.display_name,
+        action_type=action_type, message_id=None,
+        details=f"unblock_nag_count={count}",
+    ))
+    save_user_state(bot, dirty_users, user_id)
diff --git a/config.yaml b/config.yaml
index e410376..b74843c 100644
--- a/config.yaml
+++ b/config.yaml
@@ -36,6 +36,11 @@ topic_drift:
   escalation_count: 3  # After this many reminds, DM the server owner
   reset_minutes: 60  # Reset off-topic count after this much on-topic behavior
 
+unblock_nag:
+  enabled: true
+  use_llm: true  # Generate redirect messages via LLM instead of static templates
+  remind_cooldown_minutes: 30  # Don't remind same user more than once per this window
+
 mention_scan:
   enabled: true
   scan_messages: 30       # Messages to scan per mention trigger
diff --git a/prompts/unblock_redirect.txt b/prompts/unblock_redirect.txt
new file mode 100644
index 0000000..e40d345
--- /dev/null
+++ b/prompts/unblock_redirect.txt
@@ -0,0 +1,7 @@
+You're the hall monitor of "Skill Issue Support Group" (gaming Discord). Someone is asking to be unblocked — again.
+Write 1-2 sentences shutting it down. The message should make it clear that begging in chat won't help.
+
+- Snarky and playful, not cruel. Reference what they actually said — don't be vague.
+- Casual, like a friend telling them to knock it off. If nag count is 2+, escalate the sass.
+- The core message: block/unblock decisions are between them and the person who blocked them (or admins). Bringing it up in chat repeatedly is not going to change anything.
+- Max 1 emoji. No hashtags, brackets, metadata, or AI references.
\ No newline at end of file
diff --git a/utils/drama_tracker.py b/utils/drama_tracker.py
index 778cca8..c0dfada 100644
--- a/utils/drama_tracker.py
+++ b/utils/drama_tracker.py
@@ -29,6 +29,9 @@ class UserDrama:
     coherence_scores: list[float] = field(default_factory=list)
     baseline_coherence: float = 0.85
     last_coherence_alert_time: float = 0.0
+    # Unblock nagging tracking
+    unblock_nag_count: int = 0
+    last_unblock_nag_time: float = 0.0
     # Per-user LLM notes
     notes: str = ""
     # Known aliases/nicknames
@@ -256,6 +259,21 @@ class DramaTracker:
         """Return {user_id: [aliases]} for all users that have aliases set."""
         return {uid: user.aliases for uid, user in self._users.items() if user.aliases}
 
+    def record_unblock_nag(self, user_id: int) -> int:
+        user = self.get_user(user_id)
+        user.unblock_nag_count += 1
+        user.last_unblock_nag_time = time.time()
+        return user.unblock_nag_count
+
+    def can_unblock_remind(self, user_id: int, cooldown_minutes: int) -> bool:
+        user = self.get_user(user_id)
+        if user.last_unblock_nag_time == 0.0:
+            return True
+        return time.time() - user.last_unblock_nag_time > cooldown_minutes * 60
+
+    def get_unblock_nag_count(self, user_id: int) -> int:
+        return self.get_user(user_id).unblock_nag_count
+
     def reset_off_topic(self, user_id: int) -> None:
         user = self.get_user(user_id)
         user.off_topic_count = 0