diff --git a/litellm/proxy/guardrails/guardrail_endpoints.py b/litellm/proxy/guardrails/guardrail_endpoints.py
index d7b37f8a3fe..e64fbe9084e 100644
--- a/litellm/proxy/guardrails/guardrail_endpoints.py
+++ b/litellm/proxy/guardrails/guardrail_endpoints.py
@@ -564,8 +564,7 @@ async def patch_guardrail(guardrail_id: str, request: PatchGuardrailRequest):
         guardrail_name = result.get("guardrail_name", "Unknown")
 
         try:
-            IN_MEMORY_GUARDRAIL_HANDLER.update_in_memory_guardrail(
-                guardrail_id=guardrail_id,
+            IN_MEMORY_GUARDRAIL_HANDLER.sync_guardrail_from_db(
                 guardrail=guardrail,
             )
             verbose_proxy_logger.info(
diff --git a/litellm/proxy/guardrails/guardrail_registry.py b/litellm/proxy/guardrails/guardrail_registry.py
index b5ae8437d86..8aa8ba0570b 100644
--- a/litellm/proxy/guardrails/guardrail_registry.py
+++ b/litellm/proxy/guardrails/guardrail_registry.py
@@ -2,12 +2,12 @@
 
 import importlib
 import os
-from litellm._uuid import uuid
 from datetime import datetime, timezone
 from typing import Dict, List, Optional, Type, cast
 
 import litellm
 from litellm._logging import verbose_proxy_logger
+from litellm._uuid import uuid
 from litellm.integrations.custom_guardrail import CustomGuardrail
 from litellm.litellm_core_utils.safe_json_dumps import safe_dumps
 from litellm.proxy.utils import PrismaClient
@@ -525,9 +525,19 @@ class InMemoryGuardrailHandler:
 
     def delete_in_memory_guardrail(self, guardrail_id: str) -> None:
         """
-        Delete a guardrail in memory
+        Delete a guardrail in memory and remove from litellm callbacks.
         """
+        # Remove from in-memory storage
         self.IN_MEMORY_GUARDRAILS.pop(guardrail_id, None)
+        
+        # Remove the callback from litellm.callbacks
+        custom_guardrail_callback = self.guardrail_id_to_custom_guardrail.pop(guardrail_id, None)
+        if custom_guardrail_callback:
+            litellm.logging_callback_manager.remove_callback_from_list_by_object(
+                callback_list=litellm.callbacks,
+                obj=custom_guardrail_callback,
+                require_self=False
+            )
 
     def list_in_memory_guardrails(self) -> List[Guardrail]:
         """
@@ -541,6 +551,99 @@ class InMemoryGuardrailHandler:
         """
         return self.IN_MEMORY_GUARDRAILS.get(guardrail_id)
 
+    def _has_guardrail_params_changed(
+        self, guardrail_id: str, new_guardrail: Guardrail
+    ) -> bool:
+        """
+        Check if guardrail params or name have changed compared to in-memory version.
+        Returns True if params/name changed or guardrail doesn't exist in memory.
+        """
+        existing = self.IN_MEMORY_GUARDRAILS.get(guardrail_id)
+        if existing is None:
+            return True
+        
+        # Compare guardrail_name
+        if existing.get("guardrail_name") != new_guardrail.get("guardrail_name"):
+            return True
+        
+        # Compare litellm_params
+        existing_params = existing.get("litellm_params")
+        new_params = new_guardrail.get("litellm_params")
+        
+        # Convert to dicts for comparison
+        existing_dict = (
+            existing_params.model_dump() 
+            if isinstance(existing_params, LitellmParams) 
+            else existing_params
+        )
+        new_dict = (
+            new_params.model_dump() 
+            if isinstance(new_params, LitellmParams) 
+            else new_params
+        )
+        
+        # Compare and identify specific differences
+        changed_fields = {}
+        all_keys = set(existing_dict.keys()) | set(new_dict.keys())
+        for key in all_keys:
+            old_val = existing_dict.get(key)
+            new_val = new_dict.get(key)
+            if old_val != new_val:
+                changed_fields[key] = {"old": old_val, "new": new_val}
+        
+        # Log differences if any found
+        if changed_fields:
+            verbose_proxy_logger.debug(
+                f"Guardrail params changed. Differences: {changed_fields}"
+            )
+        
+        # Return True if any fields changed
+        return len(changed_fields) > 0
+
+    def reinitialize_guardrail(
+        self, guardrail: Guardrail, config_file_path: Optional[str] = None
+    ) -> Optional[Guardrail]:
+        """
+        Force re-initialization of a guardrail even if it exists in memory.
+        Removes old callback from litellm.callbacks and creates fresh instance.
+        """
+        guardrail_id = guardrail.get("guardrail_id")
+        if not guardrail_id:
+            verbose_proxy_logger.error("Cannot reinitialize guardrail without guardrail_id")
+            return None
+        
+        # Remove from memory if exists (also removes from callbacks)
+        if guardrail_id in self.IN_MEMORY_GUARDRAILS:
+            self.delete_in_memory_guardrail(guardrail_id)
+        
+        # Initialize fresh (will add new callback to litellm.callbacks)
+        return self.initialize_guardrail(
+            guardrail=guardrail, config_file_path=config_file_path
+        )
+
+    def sync_guardrail_from_db(
+        self, guardrail: Guardrail, config_file_path: Optional[str] = None
+    ) -> Optional[Guardrail]:
+        """
+        Sync a guardrail from DB - initializes if new, re-initializes if changed.
+        This is the method to call during DB polling.
+        """
+        guardrail_id = guardrail.get("guardrail_id")
+        if not guardrail_id:
+            verbose_proxy_logger.error("Cannot sync guardrail without guardrail_id")
+            return None
+        
+        if self._has_guardrail_params_changed(guardrail_id, guardrail):
+            guardrail_name = guardrail.get("guardrail_name", "Unknown")
+            verbose_proxy_logger.info(
+                f"Guardrail '{guardrail_name}' (ID: {guardrail_id}) params changed, re-initializing..."
+            )
+            return self.reinitialize_guardrail(
+                guardrail=guardrail, config_file_path=config_file_path
+            )
+        
+        return self.IN_MEMORY_GUARDRAILS.get(guardrail_id)
+
 
 ########################################################
 # In Memory Guardrail Handler for LiteLLM Proxy
diff --git a/litellm/proxy/proxy_server.py b/litellm/proxy/proxy_server.py
index 1fc8bc377e7..e57820e1248 100644
--- a/litellm/proxy/proxy_server.py
+++ b/litellm/proxy/proxy_server.py
@@ -3595,7 +3595,7 @@ class ProxyConfig:
                 "guardrails from the DB %s", str(guardrails_in_db)
             )
             for guardrail in guardrails_in_db:
-                IN_MEMORY_GUARDRAIL_HANDLER.initialize_guardrail(
+                IN_MEMORY_GUARDRAIL_HANDLER.sync_guardrail_from_db(
                     guardrail=cast(Guardrail, guardrail),
                 )
         except Exception as e:
diff --git a/ui/litellm-dashboard/src/components/guardrails/content_filter/ContentFilterManager.test.tsx b/ui/litellm-dashboard/src/components/guardrails/content_filter/ContentFilterManager.test.tsx
new file mode 100644
index 00000000000..6d879e1c544
--- /dev/null
+++ b/ui/litellm-dashboard/src/components/guardrails/content_filter/ContentFilterManager.test.tsx
@@ -0,0 +1,77 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import { render, screen, waitFor } from "@testing-library/react";
+import ContentFilterManager from "./ContentFilterManager";
+import React from "react";
+
+vi.mock("./ContentFilterConfiguration", () => ({
+  default: () => <div data-testid="content-filter-config">Mock Content Filter Configuration</div>
+}));
+
+vi.mock("./ContentFilterDisplay", () => ({
+  default: () => <div data-testid="content-filter-display">Mock Content Filter Display</div>
+}));
+
+vi.mock("antd", () => ({
+  Divider: ({ children }: { children: React.ReactNode }) => <div>{children}</div>
+}));
+
+describe("ContentFilterManager - Unsaved Changes Detection", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+  });
+
+  it("should call onUnsavedChanges with false when component initializes with matching data", async () => {
+    /**
+     * Tests that the ContentFilterManager correctly initializes the unsaved changes
+     * detection and calls onUnsavedChanges(false) when the current state matches
+     * the original loaded state (no changes yet).
+     */
+    const mockOnUnsavedChanges = vi.fn();
+    const mockOnDataChange = vi.fn();
+
+    const guardrailData = {
+      litellm_params: {
+        guardrail: "litellm_content_filter",
+        patterns: [
+          { pattern_type: "prebuilt", pattern_name: "email", action: "BLOCK" }
+        ],
+        blocked_words: [
+          { keyword: "test", action: "BLOCK", description: null }
+        ]
+      }
+    };
+
+    const guardrailSettings = {
+      content_filter_settings: {
+        prebuilt_patterns: [],
+        pattern_categories: ["PII"],
+        supported_actions: ["BLOCK", "MASK"]
+      }
+    };
+
+    render(
+      <ContentFilterManager
+        guardrailData={guardrailData}
+        guardrailSettings={guardrailSettings}
+        isEditing={true}
+        accessToken="test-token"
+        onDataChange={mockOnDataChange}
+        onUnsavedChanges={mockOnUnsavedChanges}
+      />
+    );
+
+    // Wait for component to render in edit mode
+    await waitFor(() => {
+      expect(screen.getByTestId("content-filter-config")).toBeInTheDocument();
+    });
+
+    // Verify onUnsavedChanges was called with false (no changes initially)
+    await waitFor(() => {
+      expect(mockOnUnsavedChanges).toHaveBeenCalledWith(false);
+    });
+
+    // Verify onDataChange was called with initial data
+    expect(mockOnDataChange).toHaveBeenCalled();
+  });
+});
+
diff --git a/ui/litellm-dashboard/src/components/guardrails/content_filter/ContentFilterManager.tsx b/ui/litellm-dashboard/src/components/guardrails/content_filter/ContentFilterManager.tsx
index 65a27388a22..f81aa478b93 100644
--- a/ui/litellm-dashboard/src/components/guardrails/content_filter/ContentFilterManager.tsx
+++ b/ui/litellm-dashboard/src/components/guardrails/content_filter/ContentFilterManager.tsx
@@ -38,6 +38,7 @@ interface ContentFilterManagerProps {
   isEditing: boolean;
   accessToken: string | null;
   onDataChange?: (patterns: Pattern[], blockedWords: BlockedWord[]) => void;
+  onUnsavedChanges?: (hasChanges: boolean) => void;
 }
 
 const ContentFilterManager: React.FC<ContentFilterManagerProps> = ({
@@ -46,9 +47,12 @@ const ContentFilterManager: React.FC<ContentFilterManagerProps> = ({
   isEditing,
   accessToken,
   onDataChange,
+  onUnsavedChanges,
 }) => {
   const [selectedPatterns, setSelectedPatterns] = useState<Pattern[]>([]);
   const [blockedWords, setBlockedWords] = useState<BlockedWord[]>([]);
+  const [originalPatterns, setOriginalPatterns] = useState<Pattern[]>([]);
+  const [originalBlockedWords, setOriginalBlockedWords] = useState<BlockedWord[]>([]);
 
   // Load data from guardrail on mount or when guardrailData changes
   useEffect(() => {
@@ -62,8 +66,10 @@ const ContentFilterManager: React.FC<ContentFilterManagerProps> = ({
         action: p.action || "BLOCK",
       }));
       setSelectedPatterns(patterns);
+      setOriginalPatterns(patterns);
     } else {
       setSelectedPatterns([]);
+      setOriginalPatterns([]);
     }
 
     if (guardrailData?.litellm_params?.blocked_words) {
@@ -74,8 +80,10 @@ const ContentFilterManager: React.FC<ContentFilterManagerProps> = ({
         description: w.description,
       }));
       setBlockedWords(words);
+      setOriginalBlockedWords(words);
     } else {
       setBlockedWords([]);
+      setOriginalBlockedWords([]);
     }
   }, [guardrailData]);
 
@@ -86,6 +94,19 @@ const ContentFilterManager: React.FC<ContentFilterManagerProps> = ({
     }
   }, [selectedPatterns, blockedWords, onDataChange]);
 
+  // Detect unsaved changes
+  const hasUnsavedChanges = React.useMemo(() => {
+    const hasPatternChanges = JSON.stringify(selectedPatterns) !== JSON.stringify(originalPatterns);
+    const hasWordChanges = JSON.stringify(blockedWords) !== JSON.stringify(originalBlockedWords);
+    return hasPatternChanges || hasWordChanges;
+  }, [selectedPatterns, blockedWords, originalPatterns, originalBlockedWords]);
+
+  useEffect(() => {
+    if (isEditing && onUnsavedChanges) {
+      onUnsavedChanges(hasUnsavedChanges);
+    }
+  }, [hasUnsavedChanges, isEditing, onUnsavedChanges]);
+
   // Check if this is a content filter guardrail
   if (guardrailData?.litellm_params?.guardrail !== "litellm_content_filter") {
     return null;
@@ -106,6 +127,13 @@ const ContentFilterManager: React.FC<ContentFilterManagerProps> = ({
   return (
     <>
       <Divider orientation="left">Content Filter Configuration</Divider>
+      {hasUnsavedChanges && (
+        <div className="mb-4 px-4 py-3 bg-yellow-50 border border-yellow-200 rounded-md">
+          <p className="text-sm text-yellow-800 font-medium">
+            ⚠️ You have unsaved changes to patterns or keywords. Remember to click "Save Changes" at the bottom.
+          </p>
+        </div>
+      )}
       <div className="mb-6">
         {guardrailSettings && guardrailSettings.content_filter_settings && (
           <ContentFilterConfiguration
diff --git a/ui/litellm-dashboard/src/components/guardrails/guardrail_info.tsx b/ui/litellm-dashboard/src/components/guardrails/guardrail_info.tsx
index 6a84e542dd7..a92343e8456 100644
--- a/ui/litellm-dashboard/src/components/guardrails/guardrail_info.tsx
+++ b/ui/litellm-dashboard/src/components/guardrails/guardrail_info.tsx
@@ -1,4 +1,4 @@
-import React, { useState, useEffect } from "react";
+import React, { useState, useEffect, useCallback } from "react";
 import {
   Card,
   Title,
@@ -82,12 +82,19 @@ const GuardrailInfoView: React.FC<GuardrailInfoProps> = ({ guardrailId, onClose,
     };
   } | null>(null);
   const [copiedStates, setCopiedStates] = useState<Record<string, boolean>>({});
+  const [hasUnsavedContentFilterChanges, setHasUnsavedContentFilterChanges] = useState(false);
   
   // Content Filter data ref (managed by ContentFilterManager)
   const contentFilterDataRef = React.useRef<{ patterns: any[]; blockedWords: any[] }>({
     patterns: [],
     blockedWords: [],
   });
+
+  // Memoize onDataChange callback to prevent unnecessary re-renders
+  const handleContentFilterDataChange = useCallback((patterns: any[], blockedWords: any[]) => {
+    contentFilterDataRef.current = { patterns, blockedWords };
+  }, []);
+
   const fetchGuardrailInfo = async () => {
     try {
       setLoading(true);
@@ -329,6 +336,7 @@ const GuardrailInfoView: React.FC<GuardrailInfoProps> = ({ guardrailId, onClose,
 
       await updateGuardrailCall(accessToken, guardrailId, updateData);
       NotificationsManager.success("Guardrail updated successfully");
+      setHasUnsavedContentFilterChanges(false);
       fetchGuardrailInfo();
       setIsEditing(false);
     } catch (error) {
@@ -561,9 +569,8 @@ const GuardrailInfoView: React.FC<GuardrailInfoProps> = ({ guardrailId, onClose,
                       guardrailSettings={guardrailSettings}
                       isEditing={true}
                       accessToken={accessToken}
-                      onDataChange={(patterns, blockedWords) => {
-                        contentFilterDataRef.current = { patterns, blockedWords };
-                      }}
+                      onDataChange={handleContentFilterDataChange}
+                      onUnsavedChanges={setHasUnsavedContentFilterChanges}
                     />
 
                     <Divider orientation="left">Provider Settings</Divider>
@@ -608,7 +615,10 @@ const GuardrailInfoView: React.FC<GuardrailInfoProps> = ({ guardrailId, onClose,
                     </Form.Item>
 
                     <div className="flex justify-end gap-2 mt-6">
-                      <Button onClick={() => setIsEditing(false)}>Cancel</Button>
+                      <Button onClick={() => {
+                        setIsEditing(false);
+                        setHasUnsavedContentFilterChanges(false);
+                      }}>Cancel</Button>
                       <TremorButton>Save Changes</TremorButton>
                     </div>
                   </Form>