diff --git a/litellm/proxy/guardrails/guardrail_hooks/litellm_content_filter/categories/prompt_injection_sql.yaml b/litellm/proxy/guardrails/guardrail_hooks/litellm_content_filter/categories/prompt_injection_sql.yaml
index 1af2cddef59..9519b8e4beb 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/litellm_content_filter/categories/prompt_injection_sql.yaml
+++ b/litellm/proxy/guardrails/guardrail_hooks/litellm_content_filter/categories/prompt_injection_sql.yaml
@@ -1,5 +1,7 @@
 # SQL Injection Detection - Detects SQL injection attempts in prompts
 # Uses conditional logic: BLOCK if an identifier word + block word appear in same sentence
+# NOTE: avoid regex-special characters like ( ) [ ] in keywords,
+# because the content filter matches keywords via regex internally.
 category_name: "prompt_injection_sql"
 description: "Detects SQL injection attempts embedded in prompts"
 default_action: "BLOCK"
@@ -19,32 +21,39 @@ identifier_words:
   - "TRUNCATE"
   - "GRANT"
   - "REVOKE"
+  - "UNION"
+  - "SHUTDOWN"
 
 # ADDITIONAL BLOCK WORDS - Injection-specific patterns
 additional_block_words:
-  - "UNION"
   - "1=1"
   - "OR true"
   - "OR 1"
   - "--"
-  - "/*"
   - "xp_cmdshell"
   - "information_schema"
   - "sys.tables"
+  - "sysobjects"
+  - "pg_catalog"
+  - "pg_tables"
   - "INTO OUTFILE"
+  - "INTO DUMPFILE"
   - "LOAD_FILE"
   - "BENCHMARK"
-  - "SLEEP("
   - "WAITFOR"
   - "HAVING 1=1"
-  - "GROUP BY"
   - "ORDER BY 1"
-  - "INTO DUMPFILE"
-  - "hex("
-  - "char("
-  - "concat("
-  - "@@version"
   - "schema_name"
+  - "@@version"
+  - "drop table"
+  - "drop database"
+  - "drop schema"
+  - "truncate table"
+  - "delete from"
+  - "alter table"
+  - "union select"
+  - "union all select"
+  - "grant all"
 
 # ALWAYS BLOCK - Explicit SQL injection patterns (blocked regardless of context)
 always_block_keywords:
@@ -56,6 +65,8 @@ always_block_keywords:
     severity: "high"
   - keyword: "' OR 1=1--"
     severity: "high"
+  - keyword: "' OR 1=1 --"
+    severity: "high"
   - keyword: "UNION SELECT * FROM"
     severity: "high"
   - keyword: "UNION ALL SELECT"
@@ -66,22 +77,18 @@ always_block_keywords:
     severity: "high"
   - keyword: "' UNION SELECT NULL"
     severity: "high"
-  - keyword: "SELECT * FROM users"
-    severity: "medium"
+  - keyword: "' UNION SELECT"
+    severity: "high"
+  - keyword: "UNION SELECT NULL"
+    severity: "high"
   - keyword: "SELECT password FROM"
     severity: "high"
-  - keyword: "INSERT INTO users"
-    severity: "medium"
-  - keyword: "UPDATE users SET"
-    severity: "medium"
   - keyword: "DELETE FROM users"
     severity: "high"
   - keyword: "DROP DATABASE"
     severity: "high"
   - keyword: "DROP TABLE users"
     severity: "high"
-  - keyword: "ALTER TABLE users"
-    severity: "medium"
   - keyword: "' OR ''='"
     severity: "high"
   - keyword: "admin'--"
@@ -92,29 +99,55 @@ always_block_keywords:
     severity: "high"
   - keyword: "INFORMATION_SCHEMA.COLUMNS"
     severity: "high"
-  - keyword: "LOAD DATA INFILE"
-    severity: "high"
   - keyword: "INTO OUTFILE"
     severity: "high"
-  - keyword: "BENCHMARK(10000000"
+  - keyword: "INTO DUMPFILE"
+    severity: "high"
+  - keyword: "LOAD_FILE"
     severity: "high"
   - keyword: "WAITFOR DELAY"
     severity: "high"
-  - keyword: "SLEEP(5)"
-    severity: "medium"
+  - keyword: "'; SHUTDOWN --"
+    severity: "high"
+  - keyword: "'; EXEC sp_"
+    severity: "high"
+  - keyword: "xp_cmdshell"
+    severity: "high"
+  - keyword: "sp_addlogin"
+    severity: "high"
+  - keyword: "sp_addsrvrolemember"
+    severity: "high"
+  - keyword: "ORDER BY 1--"
+    severity: "high"
+  - keyword: "GROUP BY 1--"
+    severity: "high"
+  - keyword: "HAVING 1=1"
+    severity: "high"
 
 # Exception patterns (legitimate uses)
 exceptions:
   - "SQL tutorial"
   - "learn SQL"
   - "explain SQL"
+  - "what is SQL injection"
   - "SQL syntax"
   - "SQL documentation"
   - "database design"
   - "SQL best practices"
   - "SQL injection prevention"
   - "protect against SQL injection"
+  - "how to prevent"
+  - "how to protect"
+  - "how to defend"
   - "parameterized query"
+  - "parameterized queries"
   - "prepared statement"
+  - "prepared statements"
   - "SQL training"
   - "database course"
+  - "how to sanitize"
+  - "how to validate"
+  - "research on"
+  - "security research"
+  - "security audit"
+  - "penetration testing"