diff --git a/core/src/main/java/org/opensearch/sql/ast/dsl/AstDSL.java b/core/src/main/java/org/opensearch/sql/ast/dsl/AstDSL.java
index 93ad06011c0..bf54d2ffd89 100644
--- a/core/src/main/java/org/opensearch/sql/ast/dsl/AstDSL.java
+++ b/core/src/main/java/org/opensearch/sql/ast/dsl/AstDSL.java
@@ -113,7 +113,7 @@ public UnresolvedPlan describe(String tableName) {
   }
 
   public static UnresolvedPlan search(UnresolvedPlan input, String queryString) {
-    return new Search(input, queryString);
+    return new Search(input, queryString, null);
   }
 
   public UnresolvedPlan subqueryAlias(UnresolvedPlan child, String alias) {
diff --git a/core/src/main/java/org/opensearch/sql/ast/expression/SearchAnd.java b/core/src/main/java/org/opensearch/sql/ast/expression/SearchAnd.java
index fe7be0db13e..bdfbd9fda39 100644
--- a/core/src/main/java/org/opensearch/sql/ast/expression/SearchAnd.java
+++ b/core/src/main/java/org/opensearch/sql/ast/expression/SearchAnd.java
@@ -27,6 +27,11 @@ public String toQueryString() {
     return left.toQueryString() + " AND " + right.toQueryString();
   }
 
+  @Override
+  public String toAnonymizedString() {
+    return left.toAnonymizedString() + " AND " + right.toAnonymizedString();
+  }
+
   @Override
   public List<? extends UnresolvedExpression> getChild() {
     return Arrays.asList(left, right);
diff --git a/core/src/main/java/org/opensearch/sql/ast/expression/SearchComparison.java b/core/src/main/java/org/opensearch/sql/ast/expression/SearchComparison.java
index be099059546..c429e6f66cc 100644
--- a/core/src/main/java/org/opensearch/sql/ast/expression/SearchComparison.java
+++ b/core/src/main/java/org/opensearch/sql/ast/expression/SearchComparison.java
@@ -5,6 +5,8 @@
 
 package org.opensearch.sql.ast.expression;
 
+import static org.opensearch.sql.utils.QueryStringUtils.maskField;
+
 import java.util.Arrays;
 import java.util.List;
 import lombok.EqualsAndHashCode;
@@ -63,6 +65,12 @@ public String toQueryString() {
     }
   }
 
+  @Override
+  public String toAnonymizedString() {
+    String fieldName = QueryStringUtils.escapeFieldName(field.getField().toString());
+    return maskField(fieldName) + " " + operator.symbol + " ***";
+  }
+
   @Override
   public List<? extends UnresolvedExpression> getChild() {
     return Arrays.asList(field, value);
diff --git a/core/src/main/java/org/opensearch/sql/ast/expression/SearchExpression.java b/core/src/main/java/org/opensearch/sql/ast/expression/SearchExpression.java
index 23bf806d230..b705909445f 100644
--- a/core/src/main/java/org/opensearch/sql/ast/expression/SearchExpression.java
+++ b/core/src/main/java/org/opensearch/sql/ast/expression/SearchExpression.java
@@ -17,6 +17,13 @@ public abstract class SearchExpression extends UnresolvedExpression {
    */
   public abstract String toQueryString();
 
+  /**
+   * Convert the search expression to anonymized string
+   *
+   * @return the anonymized string
+   */
+  public abstract String toAnonymizedString();
+
   @Override
   public <R, C> R accept(AbstractNodeVisitor<R, C> nodeVisitor, C context) {
     return nodeVisitor.visitChildren(this, context);
diff --git a/core/src/main/java/org/opensearch/sql/ast/expression/SearchGroup.java b/core/src/main/java/org/opensearch/sql/ast/expression/SearchGroup.java
index 41b85f408ca..09197202dc0 100644
--- a/core/src/main/java/org/opensearch/sql/ast/expression/SearchGroup.java
+++ b/core/src/main/java/org/opensearch/sql/ast/expression/SearchGroup.java
@@ -26,6 +26,14 @@ public String toQueryString() {
     return "(" + expression.toQueryString() + ")";
   }
 
+  @Override
+  public String toAnonymizedString() {
+    if (expression instanceof SearchGroup) {
+      return expression.toAnonymizedString();
+    }
+    return "(" + expression.toAnonymizedString() + ")";
+  }
+
   @Override
   public List<? extends UnresolvedExpression> getChild() {
     return Collections.singletonList(expression);
diff --git a/core/src/main/java/org/opensearch/sql/ast/expression/SearchIn.java b/core/src/main/java/org/opensearch/sql/ast/expression/SearchIn.java
index bdbdb712a9c..8291d130dff 100644
--- a/core/src/main/java/org/opensearch/sql/ast/expression/SearchIn.java
+++ b/core/src/main/java/org/opensearch/sql/ast/expression/SearchIn.java
@@ -33,6 +33,11 @@ public String toQueryString() {
     return fieldName + ":( " + valueList + " )";
   }
 
+  @Override
+  public String toAnonymizedString() {
+    return "identifier IN ***";
+  }
+
   @Override
   public List<? extends UnresolvedExpression> getChild() {
     List<UnresolvedExpression> children = new ArrayList<>();
diff --git a/core/src/main/java/org/opensearch/sql/ast/expression/SearchLiteral.java b/core/src/main/java/org/opensearch/sql/ast/expression/SearchLiteral.java
index f27dad34bab..460615afa64 100644
--- a/core/src/main/java/org/opensearch/sql/ast/expression/SearchLiteral.java
+++ b/core/src/main/java/org/opensearch/sql/ast/expression/SearchLiteral.java
@@ -55,6 +55,11 @@ public String toQueryString() {
     return QueryStringUtils.escapeLuceneSpecialCharacters(text);
   }
 
+  @Override
+  public String toAnonymizedString() {
+    return "***";
+  }
+
   @Override
   public List<? extends UnresolvedExpression> getChild() {
     return Collections.singletonList(literal);
diff --git a/core/src/main/java/org/opensearch/sql/ast/expression/SearchNot.java b/core/src/main/java/org/opensearch/sql/ast/expression/SearchNot.java
index 3e5083b7678..b9ea7b416b4 100644
--- a/core/src/main/java/org/opensearch/sql/ast/expression/SearchNot.java
+++ b/core/src/main/java/org/opensearch/sql/ast/expression/SearchNot.java
@@ -26,6 +26,11 @@ public String toQueryString() {
     return "NOT(" + expression.toQueryString() + ")";
   }
 
+  @Override
+  public String toAnonymizedString() {
+    return "NOT(" + expression.toAnonymizedString() + ")";
+  }
+
   @Override
   public List<? extends UnresolvedExpression> getChild() {
     return Collections.singletonList(expression);
diff --git a/core/src/main/java/org/opensearch/sql/ast/expression/SearchOr.java b/core/src/main/java/org/opensearch/sql/ast/expression/SearchOr.java
index b5aa72807bd..1a9e95e89a2 100644
--- a/core/src/main/java/org/opensearch/sql/ast/expression/SearchOr.java
+++ b/core/src/main/java/org/opensearch/sql/ast/expression/SearchOr.java
@@ -27,6 +27,11 @@ public String toQueryString() {
     return left.toQueryString() + " OR " + right.toQueryString();
   }
 
+  @Override
+  public String toAnonymizedString() {
+    return left.toAnonymizedString() + " OR " + right.toAnonymizedString();
+  }
+
   @Override
   public List<? extends UnresolvedExpression> getChild() {
     return Arrays.asList(left, right);
diff --git a/core/src/main/java/org/opensearch/sql/ast/tree/Search.java b/core/src/main/java/org/opensearch/sql/ast/tree/Search.java
index ebc74192987..0a705f95c41 100644
--- a/core/src/main/java/org/opensearch/sql/ast/tree/Search.java
+++ b/core/src/main/java/org/opensearch/sql/ast/tree/Search.java
@@ -7,11 +7,13 @@
 
 import com.google.common.collect.ImmutableList;
 import java.util.List;
+import javax.annotation.Nullable;
 import lombok.EqualsAndHashCode;
 import lombok.Getter;
 import lombok.RequiredArgsConstructor;
 import lombok.ToString;
 import org.opensearch.sql.ast.AbstractNodeVisitor;
+import org.opensearch.sql.ast.expression.SearchExpression;
 
 /**
  * Logical plan node for Search operation. Represents search expressions that get converted to
@@ -19,12 +21,19 @@
  */
 @Getter
 @ToString
-@EqualsAndHashCode(callSuper = false)
+@EqualsAndHashCode(onlyExplicitlyIncluded = true, callSuper = false)
 @RequiredArgsConstructor
 public class Search extends UnresolvedPlan {
 
-  private final UnresolvedPlan child;
-  private final String queryString;
+  @EqualsAndHashCode.Include private final UnresolvedPlan child;
+  @EqualsAndHashCode.Include private final String queryString;
+
+  // Currently it's only for anonymizer
+  private final @Nullable SearchExpression originalExpression;
+
+  public Search(UnresolvedPlan child, String queryString) {
+    this(child, queryString, null);
+  }
 
   @Override
   public List<UnresolvedPlan> getChild() {
@@ -38,6 +47,6 @@ public <T, C> T accept(AbstractNodeVisitor<T, C> nodeVisitor, C context) {
 
   @Override
   public UnresolvedPlan attach(UnresolvedPlan child) {
-    return new Search(child, queryString);
+    return new Search(child, queryString, originalExpression);
   }
 }
diff --git a/core/src/main/java/org/opensearch/sql/utils/QueryStringUtils.java b/core/src/main/java/org/opensearch/sql/utils/QueryStringUtils.java
index fd9c4b7d2e3..94c1bd9db05 100644
--- a/core/src/main/java/org/opensearch/sql/utils/QueryStringUtils.java
+++ b/core/src/main/java/org/opensearch/sql/utils/QueryStringUtils.java
@@ -8,6 +8,26 @@
 /** Utility class for query_string syntax operations. */
 public class QueryStringUtils {
 
+  private static final String INTERNAL_TIMESTAMP = "@timestamp";
+
+  public static final String MASK_LITERAL = "***";
+
+  public static final String MASK_COLUMN = "identifier";
+
+  public static final String MASK_TIMESTAMP_COLUMN = "time_identifier";
+
+  public static final String MASK_METADATA_COLUMN = "meta_identifier";
+
+  public static String maskField(String fieldName) {
+    if (fieldName.equals(INTERNAL_TIMESTAMP)) {
+      return MASK_TIMESTAMP_COLUMN;
+    }
+    if (fieldName.startsWith("_")) {
+      return MASK_METADATA_COLUMN;
+    }
+    return MASK_COLUMN;
+  }
+
   // For field names, we typically don't escape dots as they're used for nested fields
   // But we escape other special characters
   public static final String LUCENE_SPECIAL_CHARS = "+-&|!(){}[]^\"~:/";
diff --git a/integ-test/src/test/resources/expectedOutput/calcite/explain_search_with_match_pushdown.json b/integ-test/src/test/resources/expectedOutput/calcite/explain_search_with_match_pushdown.json
new file mode 100644
index 00000000000..fb6ef8e36ff
--- /dev/null
+++ b/integ-test/src/test/resources/expectedOutput/calcite/explain_search_with_match_pushdown.json
@@ -0,0 +1,6 @@
+{
+  "calcite":{
+    "logical":"LogicalSystemLimit(fetch=[10000], type=[QUERY_SIZE_LIMIT])\n  LogicalProject(account_number=[$0], firstname=[$1], address=[$2], birthdate=[$3], gender=[$4], city=[$5], lastname=[$6], balance=[$7], employer=[$8], state=[$9], age=[$10], email=[$11], male=[$12])\n    LogicalFilter(condition=[match(MAP('field_name', $3), MAP('value', '\"2016\\-12\\-08 00\\:00\\:00.000000000\"':VARCHAR))])\n      CalciteLogicalIndexScan(table=[[OpenSearch, opensearch-sql_test_index_bank]])\n",
+    "physical":"CalciteEnumerableIndexScan(table=[[OpenSearch, opensearch-sql_test_index_bank]], PushDownContext=[[PROJECT->[account_number, firstname, address, birthdate, gender, city, lastname, balance, employer, state, age, email, male], FILTER->match(MAP('field_name', $3), MAP('value', '\"2016\\-12\\-08 00\\:00\\:00.000000000\"':VARCHAR)), LIMIT->10000], OpenSearchRequestBuilder(sourceBuilder={\"from\":0,\"size\":10000,\"timeout\":\"1m\",\"query\":{\"match\":{\"birthdate\":{\"query\":\"\\\"2016\\\\-12\\\\-08 00\\\\:00\\\\:00.000000000\\\"\",\"operator\":\"OR\",\"prefix_length\":0,\"max_expansions\":50,\"fuzzy_transpositions\":true,\"lenient\":false,\"zero_terms_query\":\"NONE\",\"auto_generate_synonyms_phrase_query\":true,\"boost\":1.0}}},\"_source\":{\"includes\":[\"account_number\",\"firstname\",\"address\",\"birthdate\",\"gender\",\"city\",\"lastname\",\"balance\",\"employer\",\"state\",\"age\",\"email\",\"male\"],\"excludes\":[]}}, requestedTotalSize=10000, pageSize=null, startFrom=0)])\n"
+  }
+}
\ No newline at end of file
diff --git a/ppl/src/main/java/org/opensearch/sql/ppl/parser/AstBuilder.java b/ppl/src/main/java/org/opensearch/sql/ppl/parser/AstBuilder.java
index ed66682a981..9eedaeed2d8 100644
--- a/ppl/src/main/java/org/opensearch/sql/ppl/parser/AstBuilder.java
+++ b/ppl/src/main/java/org/opensearch/sql/ppl/parser/AstBuilder.java
@@ -214,7 +214,7 @@ public UnresolvedPlan visitSearchFrom(SearchFromContext ctx) {
 
       // Create Search node with relation and query string
       Relation relation = (Relation) visitFromClause(ctx.fromClause());
-      return new Search(relation, queryString);
+      return new Search(relation, queryString, combined);
     }
   }
 
diff --git a/ppl/src/main/java/org/opensearch/sql/ppl/utils/PPLQueryDataAnonymizer.java b/ppl/src/main/java/org/opensearch/sql/ppl/utils/PPLQueryDataAnonymizer.java
index 7e8dc16f4dd..e277dfacbc1 100644
--- a/ppl/src/main/java/org/opensearch/sql/ppl/utils/PPLQueryDataAnonymizer.java
+++ b/ppl/src/main/java/org/opensearch/sql/ppl/utils/PPLQueryDataAnonymizer.java
@@ -7,6 +7,9 @@
 
 import static org.opensearch.sql.calcite.utils.PlanUtils.getRelation;
 import static org.opensearch.sql.calcite.utils.PlanUtils.transformPlanToAttachChild;
+import static org.opensearch.sql.utils.QueryStringUtils.MASK_COLUMN;
+import static org.opensearch.sql.utils.QueryStringUtils.MASK_LITERAL;
+import static org.opensearch.sql.utils.QueryStringUtils.maskField;
 
 import com.google.common.base.Strings;
 import com.google.common.collect.ImmutableList;
@@ -108,11 +111,7 @@
 /** Utility class to mask sensitive information in incoming PPL queries. */
 public class PPLQueryDataAnonymizer extends AbstractNodeVisitor<String, String> {
 
-  private static final String MASK_LITERAL = "***";
-
-  private static final String MASK_COLUMN = "identifier";
-
-  private static final String MASK_TABLE = "table";
+  public static final String MASK_TABLE = "table";
 
   private final AnonymizerExpressionAnalyzer expressionAnalyzer;
   private final Settings settings;
@@ -252,9 +251,7 @@ public String visitTableFunction(TableFunction node, String context) {
   @Override
   public String visitSearch(Search node, String context) {
     String source = node.getChild().get(0).accept(this, context);
-    String queryString = node.getQueryString();
-    String anonymized = queryString.replaceAll(":\\S+", ":" + MASK_LITERAL);
-    return StringUtils.format("%s %s", source, anonymized);
+    return StringUtils.format("%s %s", source, node.getOriginalExpression().toAnonymizedString());
   }
 
   @Override
@@ -918,7 +915,8 @@ public String visitIn(In node, String context) {
 
     @Override
     public String visitField(Field node, String context) {
-      return MASK_COLUMN;
+      String fieldName = node.getField().toString();
+      return maskField(fieldName);
     }
 
     @Override
diff --git a/ppl/src/test/java/org/opensearch/sql/ppl/utils/PPLQueryDataAnonymizerTest.java b/ppl/src/test/java/org/opensearch/sql/ppl/utils/PPLQueryDataAnonymizerTest.java
index f205b9fe0cc..549fca03195 100644
--- a/ppl/src/test/java/org/opensearch/sql/ppl/utils/PPLQueryDataAnonymizerTest.java
+++ b/ppl/src/test/java/org/opensearch/sql/ppl/utils/PPLQueryDataAnonymizerTest.java
@@ -33,7 +33,7 @@ public class PPLQueryDataAnonymizerTest {
 
   @Test
   public void testSearchCommand() {
-    assertEquals("source=table a:***", anonymize("search source=t a=1"));
+    assertEquals("source=table identifier = ***", anonymize("search source=t a=1"));
   }
 
   @Test
@@ -255,8 +255,8 @@ public void testReverseCommand() {
   @Test
   public void testTimechartCommand() {
     assertEquals(
-        "source=table | timechart limit=*** useother=*** count() by span(identifier, *** m)"
-            + " identifier",
+        "source=table | timechart limit=*** useother=*** count() by span(time_identifier, ***"
+            + " m) identifier",
         anonymize("source=t | timechart count() by host"));
   }
 
@@ -388,6 +388,13 @@ public void testAndExpression() {
         anonymize("source=t | where a=1 and b=2"));
   }
 
+  @Test
+  public void testAndExpressionWithMetaData() {
+    assertEquals(
+        "source=table | where meta_identifier = *** and identifier = ***",
+        anonymize("source=t | where _id=1 and b=2"));
+  }
+
   @Test
   public void testOrExpression() {
     assertEquals(
@@ -879,10 +886,37 @@ private String anonymizeStatement(String query, boolean isExplain) {
   @Test
   public void testSearchWithAbsoluteTimeRange() {
     assertEquals(
-        "source=table (@timestamp:*** AND (@timestamp:***",
+        "source=table (time_identifier >= ***) AND (time_identifier <= ***)",
         anonymize("search source=t earliest='2012-12-10 15:00:00' latest=now"));
   }
 
+  @Test
+  public void testSearchWithIn() {
+    assertEquals("source=table identifier IN ***", anonymize("search source=t balance in (2000)"));
+  }
+
+  @Test
+  public void testSearchWithNot() {
+    assertEquals(
+        "source=table NOT(identifier = ***)", anonymize("search NOT balance=2000 source=t"));
+  }
+
+  @Test
+  public void testSearchWithGroup() {
+    assertEquals(
+        "source=table ((identifier = *** OR identifier = ***) AND identifier > ***)",
+        anonymize(
+            "search (severityText=\"ERROR\" OR severityText=\"WARN\") AND severityNumber>10"
+                + " source=t"));
+  }
+
+  @Test
+  public void testSearchWithOr() {
+    assertEquals(
+        "source=table (time_identifier >= *** OR time_identifier <= ***)",
+        anonymize("search source=t earliest='2012-12-10 15:00:00' or latest=now"));
+  }
+
   @Test
   public void testSpath() {
     assertEquals(