diff --git a/api/src/test/java/org/opensearch/sql/api/UnifiedQueryPlannerTest.java b/api/src/test/java/org/opensearch/sql/api/UnifiedQueryPlannerTest.java
index f8cc834dee8..00bceba9fe2 100644
--- a/api/src/test/java/org/opensearch/sql/api/UnifiedQueryPlannerTest.java
+++ b/api/src/test/java/org/opensearch/sql/api/UnifiedQueryPlannerTest.java
@@ -171,7 +171,8 @@ public void unsupportedWindowFunctionIsRethrownAsSemanticCheckException() {
     givenInvalidQuery("source = catalog.employees | eventstats percent_rank()")
         .assertErrorType(SemanticCheckException.class)
         .assertCauseType(CalciteUnsupportedException.class)
-        .assertErrorMessageContains("Unexpected window function: percent_rank");
+        .assertErrorMessageContains(
+            "Window function 'percent_rank' is not supported in eventstats/streamstats");
   }
 
   @Test
diff --git a/core/src/main/java/org/opensearch/sql/calcite/CalciteRexNodeVisitor.java b/core/src/main/java/org/opensearch/sql/calcite/CalciteRexNodeVisitor.java
index b6500dd8087..b554cb82227 100644
--- a/core/src/main/java/org/opensearch/sql/calcite/CalciteRexNodeVisitor.java
+++ b/core/src/main/java/org/opensearch/sql/calcite/CalciteRexNodeVisitor.java
@@ -808,7 +808,14 @@ public RexNode visitWindowFunction(WindowFunction node, CalcitePlanContext conte
                       node.getWindowFrame());
             })
         .orElseThrow(
-            () -> new CalciteUnsupportedException("Unexpected window function: " + funcName));
+            () ->
+                new CalciteUnsupportedException(
+                    "Window function '"
+                        + funcName
+                        + "' is not supported in eventstats/streamstats."
+                        + " Supported functions: avg, count, dc, distinct_count, earliest,"
+                        + " latest, max, min, row_number, stddev_pop, stddev_samp, sum,"
+                        + " var_pop, var_samp."));
   }
 
   private List<RexNode> translateOrderKeys(
diff --git a/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalcitePPLEventstatsIT.java b/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalcitePPLEventstatsIT.java
index a2d1e4af086..9c0bd5422c5 100644
--- a/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalcitePPLEventstatsIT.java
+++ b/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalcitePPLEventstatsIT.java
@@ -12,6 +12,7 @@
 import java.util.List;
 import org.json.JSONObject;
 import org.junit.jupiter.api.Test;
+import org.opensearch.sql.common.antlr.SyntaxCheckException;
 import org.opensearch.sql.ppl.PPLIntegTestCase;
 
 public class CalcitePPLEventstatsIT extends PPLIntegTestCase {
@@ -329,7 +330,23 @@ public void testUnsupportedWindowFunctions() {
                   executeQuery(
                       String.format(
                           "source=%s | eventstats %s(age)", TEST_INDEX_STATE_COUNTRY, u)));
-      verifyErrorMessageContains(e, "Unexpected window function: " + u);
+      verifyErrorMessageContains(e, "is not supported in eventstats/streamstats");
+    }
+  }
+
+  @Test
+  public void testRankingWindowFunctionsUnsupportedInEventstats() {
+    // rank/dense_rank aren't in eventstats/streamstats' windowFunctionName grammar rule, so this
+    // is now a parse-time rejection rather than a semantic one.
+    for (String func : List.of("rank", "dense_rank")) {
+      Throwable e =
+          assertThrowsWithReplace(
+              SyntaxCheckException.class,
+              () ->
+                  executeQuery(
+                      String.format(
+                          "source=%s | eventstats %s() by state", TEST_INDEX_STATE_COUNTRY, func)));
+      verifyErrorMessageContains(e, "is not a valid term at this part of the query");
     }
   }
 
diff --git a/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalciteStreamstatsCommandIT.java b/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalciteStreamstatsCommandIT.java
index e70812e3c3b..81c653b0742 100644
--- a/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalciteStreamstatsCommandIT.java
+++ b/integ-test/src/test/java/org/opensearch/sql/calcite/remote/CalciteStreamstatsCommandIT.java
@@ -16,6 +16,7 @@
 import org.json.JSONObject;
 import org.junit.jupiter.api.Test;
 import org.opensearch.client.Request;
+import org.opensearch.sql.common.antlr.SyntaxCheckException;
 import org.opensearch.sql.ppl.PPLIntegTestCase;
 import org.opensearch.sql.util.RequiresCapability;
 
@@ -846,7 +847,24 @@ public void testUnsupportedWindowFunctions() {
                   executeQuery(
                       String.format(
                           "source=%s | streamstats %s(age)", TEST_INDEX_STATE_COUNTRY, u)));
-      verifyErrorMessageContains(e, "Unexpected window function: " + u);
+      verifyErrorMessageContains(e, "is not supported in eventstats/streamstats");
+    }
+  }
+
+  @Test
+  public void testRankingWindowFunctionsUnsupportedInStreamstats() {
+    // rank/dense_rank aren't in eventstats/streamstats' windowFunctionName grammar rule, so this
+    // is now a parse-time rejection rather than a semantic one.
+    for (String func : List.of("rank", "dense_rank")) {
+      Throwable e =
+          assertThrowsWithReplace(
+              SyntaxCheckException.class,
+              () ->
+                  executeQuery(
+                      String.format(
+                          "source=%s | streamstats %s() by state",
+                          TEST_INDEX_STATE_COUNTRY, func)));
+      verifyErrorMessageContains(e, "is not a valid term at this part of the query");
     }
   }
 
diff --git a/ppl/src/main/antlr/OpenSearchPPLParser.g4 b/ppl/src/main/antlr/OpenSearchPPLParser.g4
index ce949f8534b..b8280043aeb 100644
--- a/ppl/src/main/antlr/OpenSearchPPLParser.g4
+++ b/ppl/src/main/antlr/OpenSearchPPLParser.g4
@@ -930,8 +930,6 @@ windowFunctionName
 
 scalarWindowFunctionName
    : ROW_NUMBER
-   | RANK
-   | DENSE_RANK
    | PERCENT_RANK
    | CUME_DIST
    | FIRST