diff --git a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/Equals.java b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/Equals.java
index 32e15deb07b4e..614d9aa3ec920 100644
--- a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/Equals.java
+++ b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/Equals.java
@@ -35,6 +35,7 @@ public class Equals extends EsqlBinaryComparison implements Negatable<EsqlBinary
         Map.entry(DataType.LONG, EqualsLongsEvaluator.Factory::new),
         Map.entry(DataType.UNSIGNED_LONG, EqualsLongsEvaluator.Factory::new),
         Map.entry(DataType.DATETIME, EqualsLongsEvaluator.Factory::new),
+        Map.entry(DataType.DATE_NANOS, EqualsLongsEvaluator.Factory::new),
         Map.entry(DataType.GEO_POINT, EqualsGeometriesEvaluator.Factory::new),
         Map.entry(DataType.CARTESIAN_POINT, EqualsGeometriesEvaluator.Factory::new),
         Map.entry(DataType.GEO_SHAPE, EqualsGeometriesEvaluator.Factory::new),
diff --git a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThan.java b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThan.java
index 33981a3337737..6aef5c76f7385 100644
--- a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThan.java
+++ b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThan.java
@@ -34,6 +34,7 @@ public class GreaterThan extends EsqlBinaryComparison implements Negatable<EsqlB
         Map.entry(DataType.LONG, GreaterThanLongsEvaluator.Factory::new),
         Map.entry(DataType.UNSIGNED_LONG, GreaterThanLongsEvaluator.Factory::new),
         Map.entry(DataType.DATETIME, GreaterThanLongsEvaluator.Factory::new),
+        Map.entry(DataType.DATE_NANOS, GreaterThanLongsEvaluator.Factory::new),
         Map.entry(DataType.KEYWORD, GreaterThanKeywordsEvaluator.Factory::new),
         Map.entry(DataType.TEXT, GreaterThanKeywordsEvaluator.Factory::new),
         Map.entry(DataType.VERSION, GreaterThanKeywordsEvaluator.Factory::new),
diff --git a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanOrEqual.java b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanOrEqual.java
index ffcd99558c6ad..1b1d301428d73 100644
--- a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanOrEqual.java
+++ b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanOrEqual.java
@@ -34,6 +34,7 @@ public class GreaterThanOrEqual extends EsqlBinaryComparison implements Negatabl
         Map.entry(DataType.LONG, GreaterThanOrEqualLongsEvaluator.Factory::new),
         Map.entry(DataType.UNSIGNED_LONG, GreaterThanOrEqualLongsEvaluator.Factory::new),
         Map.entry(DataType.DATETIME, GreaterThanOrEqualLongsEvaluator.Factory::new),
+        Map.entry(DataType.DATE_NANOS, GreaterThanOrEqualLongsEvaluator.Factory::new),
         Map.entry(DataType.KEYWORD, GreaterThanOrEqualKeywordsEvaluator.Factory::new),
         Map.entry(DataType.TEXT, GreaterThanOrEqualKeywordsEvaluator.Factory::new),
         Map.entry(DataType.VERSION, GreaterThanOrEqualKeywordsEvaluator.Factory::new),
diff --git a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThan.java b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThan.java
index a9a1f774f4ebb..333b18e21ab1b 100644
--- a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThan.java
+++ b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThan.java
@@ -34,6 +34,7 @@ public class LessThan extends EsqlBinaryComparison implements Negatable<EsqlBina
         Map.entry(DataType.LONG, LessThanLongsEvaluator.Factory::new),
         Map.entry(DataType.UNSIGNED_LONG, LessThanLongsEvaluator.Factory::new),
         Map.entry(DataType.DATETIME, LessThanLongsEvaluator.Factory::new),
+        Map.entry(DataType.DATE_NANOS, LessThanLongsEvaluator.Factory::new),
         Map.entry(DataType.KEYWORD, LessThanKeywordsEvaluator.Factory::new),
         Map.entry(DataType.TEXT, LessThanKeywordsEvaluator.Factory::new),
         Map.entry(DataType.VERSION, LessThanKeywordsEvaluator.Factory::new),
diff --git a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanOrEqual.java b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanOrEqual.java
index 5623750ea0f91..94c3911a02f64 100644
--- a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanOrEqual.java
+++ b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanOrEqual.java
@@ -34,6 +34,7 @@ public class LessThanOrEqual extends EsqlBinaryComparison implements Negatable<E
         Map.entry(DataType.LONG, LessThanOrEqualLongsEvaluator.Factory::new),
         Map.entry(DataType.UNSIGNED_LONG, LessThanOrEqualLongsEvaluator.Factory::new),
         Map.entry(DataType.DATETIME, LessThanOrEqualLongsEvaluator.Factory::new),
+        Map.entry(DataType.DATE_NANOS, LessThanOrEqualLongsEvaluator.Factory::new),
         Map.entry(DataType.KEYWORD, LessThanOrEqualKeywordsEvaluator.Factory::new),
         Map.entry(DataType.TEXT, LessThanOrEqualKeywordsEvaluator.Factory::new),
         Map.entry(DataType.VERSION, LessThanOrEqualKeywordsEvaluator.Factory::new),
diff --git a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/NotEquals.java b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/NotEquals.java
index d61953587f79b..abca00212b848 100644
--- a/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/NotEquals.java
+++ b/x-pack/plugin/esql/src/main/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/NotEquals.java
@@ -35,6 +35,7 @@ public class NotEquals extends EsqlBinaryComparison implements Negatable<EsqlBin
         Map.entry(DataType.LONG, NotEqualsLongsEvaluator.Factory::new),
         Map.entry(DataType.UNSIGNED_LONG, NotEqualsLongsEvaluator.Factory::new),
         Map.entry(DataType.DATETIME, NotEqualsLongsEvaluator.Factory::new),
+        Map.entry(DataType.DATE_NANOS, NotEqualsLongsEvaluator.Factory::new),
         Map.entry(DataType.GEO_POINT, NotEqualsGeometriesEvaluator.Factory::new),
         Map.entry(DataType.CARTESIAN_POINT, NotEqualsGeometriesEvaluator.Factory::new),
         Map.entry(DataType.GEO_SHAPE, NotEqualsGeometriesEvaluator.Factory::new),
diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/EqualsTests.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/EqualsTests.java
index 609f879d88372..66edd56e32f20 100644
--- a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/EqualsTests.java
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/EqualsTests.java
@@ -116,7 +116,6 @@ public static Iterable<Object[]> parameters() {
             )
         );
         // Datetime
-        // TODO: I'm surprised this passes. Shouldn't there be a cast from DateTime to Long?
         suppliers.addAll(
             TestCaseSupplier.forBinaryNotCasting(
                 "EqualsLongsEvaluator",
@@ -131,6 +130,20 @@ public static Iterable<Object[]> parameters() {
             )
         );
 
+        suppliers.addAll(
+            TestCaseSupplier.forBinaryNotCasting(
+                "EqualsLongsEvaluator",
+                "lhs",
+                "rhs",
+                Object::equals,
+                DataType.BOOLEAN,
+                TestCaseSupplier.dateNanosCases(),
+                TestCaseSupplier.dateNanosCases(),
+                List.of(),
+                false
+            )
+        );
+
         suppliers.addAll(
             TestCaseSupplier.stringCases(
                 Object::equals,
@@ -204,7 +217,7 @@ public static Iterable<Object[]> parameters() {
     }
 
     private static String typeErrorString =
-        "boolean, cartesian_point, cartesian_shape, datetime, double, geo_point, geo_shape, integer, ip, keyword, long, text, "
+        "boolean, cartesian_point, cartesian_shape, datetime, date_nanos, double, geo_point, geo_shape, integer, ip, keyword, long, text, "
             + "unsigned_long or version";
 
     @Override
diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanOrEqualTests.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanOrEqualTests.java
index 5435a7f629d43..a4d1bf69796e0 100644
--- a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanOrEqualTests.java
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanOrEqualTests.java
@@ -106,7 +106,6 @@ public static Iterable<Object[]> parameters() {
             )
         );
         // Datetime
-        // TODO: I'm surprised this passes. Shouldn't there be a cast from DateTime to Long?
         suppliers.addAll(
             TestCaseSupplier.forBinaryNotCasting(
                 "GreaterThanOrEqualLongsEvaluator",
@@ -121,6 +120,20 @@ public static Iterable<Object[]> parameters() {
             )
         );
 
+        suppliers.addAll(
+            TestCaseSupplier.forBinaryNotCasting(
+                "GreaterThanOrEqualLongsEvaluator",
+                "lhs",
+                "rhs",
+                (l, r) -> ((Number) l).longValue() >= ((Number) r).longValue(),
+                DataType.BOOLEAN,
+                TestCaseSupplier.dateNanosCases(),
+                TestCaseSupplier.dateNanosCases(),
+                List.of(),
+                false
+            )
+        );
+
         suppliers.addAll(
             TestCaseSupplier.stringCases(
                 (l, r) -> ((BytesRef) l).compareTo((BytesRef) r) >= 0,
@@ -137,7 +150,7 @@ public static Iterable<Object[]> parameters() {
                     o,
                     v,
                     t,
-                    (l, p) -> "datetime, double, integer, ip, keyword, long, text, unsigned_long or version"
+                    (l, p) -> "date_nanos, datetime, double, integer, ip, keyword, long, text, unsigned_long or version"
                 )
             )
         );
diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanTests.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanTests.java
index 75c22c34623b9..d3fede5c2e2ce 100644
--- a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanTests.java
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/GreaterThanTests.java
@@ -106,7 +106,6 @@ public static Iterable<Object[]> parameters() {
             )
         );
         // Datetime
-        // TODO: I'm surprised this passes. Shouldn't there be a cast from DateTime to Long?
         suppliers.addAll(
             TestCaseSupplier.forBinaryNotCasting(
                 "GreaterThanLongsEvaluator",
@@ -121,6 +120,20 @@ public static Iterable<Object[]> parameters() {
             )
         );
 
+        suppliers.addAll(
+            TestCaseSupplier.forBinaryNotCasting(
+                "GreaterThanLongsEvaluator",
+                "lhs",
+                "rhs",
+                (l, r) -> ((Number) l).longValue() > ((Number) r).longValue(),
+                DataType.BOOLEAN,
+                TestCaseSupplier.dateNanosCases(),
+                TestCaseSupplier.dateNanosCases(),
+                List.of(),
+                false
+            )
+        );
+
         suppliers.addAll(
             TestCaseSupplier.stringCases(
                 (l, r) -> ((BytesRef) l).compareTo((BytesRef) r) > 0,
@@ -137,7 +150,7 @@ public static Iterable<Object[]> parameters() {
                     o,
                     v,
                     t,
-                    (l, p) -> "datetime, double, integer, ip, keyword, long, text, unsigned_long or version"
+                    (l, p) -> "date_nanos, datetime, double, integer, ip, keyword, long, text, unsigned_long or version"
                 )
             )
         );
diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanOrEqualTests.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanOrEqualTests.java
index b65c6a753e14d..3b8270c1576fd 100644
--- a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanOrEqualTests.java
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanOrEqualTests.java
@@ -106,7 +106,6 @@ public static Iterable<Object[]> parameters() {
             )
         );
         // Datetime
-        // TODO: I'm surprised this passes. Shouldn't there be a cast from DateTime to Long?
         suppliers.addAll(
             TestCaseSupplier.forBinaryNotCasting(
                 "LessThanOrEqualLongsEvaluator",
@@ -121,6 +120,20 @@ public static Iterable<Object[]> parameters() {
             )
         );
 
+        suppliers.addAll(
+            TestCaseSupplier.forBinaryNotCasting(
+                "LessThanOrEqualLongsEvaluator",
+                "lhs",
+                "rhs",
+                (l, r) -> ((Number) l).longValue() <= ((Number) r).longValue(),
+                DataType.BOOLEAN,
+                TestCaseSupplier.dateNanosCases(),
+                TestCaseSupplier.dateNanosCases(),
+                List.of(),
+                false
+            )
+        );
+
         suppliers.addAll(
             TestCaseSupplier.stringCases(
                 (l, r) -> ((BytesRef) l).compareTo((BytesRef) r) <= 0,
@@ -137,7 +150,7 @@ public static Iterable<Object[]> parameters() {
                     o,
                     v,
                     t,
-                    (l, p) -> "datetime, double, integer, ip, keyword, long, text, unsigned_long or version"
+                    (l, p) -> "date_nanos, datetime, double, integer, ip, keyword, long, text, unsigned_long or version"
                 )
             )
         );
diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanTests.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanTests.java
index 88c79d506e0c7..647988fe35326 100644
--- a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanTests.java
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/LessThanTests.java
@@ -106,7 +106,20 @@ public static Iterable<Object[]> parameters() {
             )
         );
         // Datetime
-        // TODO: I'm surprised this passes. Shouldn't there be a cast from DateTime to Long?
+        suppliers.addAll(
+            TestCaseSupplier.forBinaryNotCasting(
+                "LessThanLongsEvaluator",
+                "lhs",
+                "rhs",
+                (l, r) -> ((Number) l).longValue() < ((Number) r).longValue(),
+                DataType.BOOLEAN,
+                TestCaseSupplier.dateCases(),
+                TestCaseSupplier.dateCases(),
+                List.of(),
+                false
+            )
+        );
+
         suppliers.addAll(
             TestCaseSupplier.forBinaryNotCasting(
                 "LessThanLongsEvaluator",
@@ -137,7 +150,7 @@ public static Iterable<Object[]> parameters() {
                     o,
                     v,
                     t,
-                    (l, p) -> "datetime, double, integer, ip, keyword, long, text, unsigned_long or version"
+                    (l, p) -> "date_nanos, datetime, double, integer, ip, keyword, long, text, unsigned_long or version"
                 )
             )
         );
diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/NotEqualsTests.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/NotEqualsTests.java
index 06585f7c1a49d..53676a43b16a0 100644
--- a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/NotEqualsTests.java
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/comparison/NotEqualsTests.java
@@ -115,7 +115,6 @@ public static Iterable<Object[]> parameters() {
             )
         );
         // Datetime
-        // TODO: I'm surprised this passes. Shouldn't there be a cast from DateTime to Long?
         suppliers.addAll(
             TestCaseSupplier.forBinaryNotCasting(
                 "NotEqualsLongsEvaluator",
@@ -129,6 +128,20 @@ public static Iterable<Object[]> parameters() {
                 false
             )
         );
+        // Datetime
+        suppliers.addAll(
+            TestCaseSupplier.forBinaryNotCasting(
+                "NotEqualsLongsEvaluator",
+                "lhs",
+                "rhs",
+                (l, r) -> false == l.equals(r),
+                DataType.BOOLEAN,
+                TestCaseSupplier.dateNanosCases(),
+                TestCaseSupplier.dateNanosCases(),
+                List.of(),
+                false
+            )
+        );
         suppliers.addAll(
             TestCaseSupplier.stringCases(
                 (l, r) -> false == l.equals(r),
@@ -198,7 +211,7 @@ public static Iterable<Object[]> parameters() {
     }
 
     private static String typeErrorString =
-        "boolean, cartesian_point, cartesian_shape, datetime, double, geo_point, geo_shape, integer, ip, keyword, long, text, "
+        "boolean, cartesian_point, cartesian_shape, datetime, date_nanos, double, geo_point, geo_shape, integer, ip, keyword, long, text, "
             + "unsigned_long or version";
 
     @Override