diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/function/TestCaseSupplier.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/function/TestCaseSupplier.java
index 1413d1193acc3..7cfe950bb3144 100644
--- a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/function/TestCaseSupplier.java
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/function/TestCaseSupplier.java
@@ -427,6 +427,30 @@ public static List<TestCaseSupplier> forBinaryNotCasting(
         List<TypedDataSupplier> rhsSuppliers,
         List<String> warnings,
         boolean symmetric
+    ) {
+        return forBinaryNotCasting(
+            name,
+            lhsName,
+            rhsName,
+            expected,
+            expectedType,
+            lhsSuppliers,
+            rhsSuppliers,
+            (lhs, rhs) -> warnings,
+            symmetric
+        );
+    }
+
+    public static List<TestCaseSupplier> forBinaryNotCasting(
+        String name,
+        String lhsName,
+        String rhsName,
+        BinaryOperator<Object> expected,
+        DataType expectedType,
+        List<TypedDataSupplier> lhsSuppliers,
+        List<TypedDataSupplier> rhsSuppliers,
+        BiFunction<TypedData, TypedData, List<String>> warnings,
+        boolean symmetric
     ) {
         List<TestCaseSupplier> suppliers = new ArrayList<>();
         casesCrossProduct(
@@ -434,7 +458,7 @@ public static List<TestCaseSupplier> forBinaryNotCasting(
             lhsSuppliers,
             rhsSuppliers,
             (lhsType, rhsType) -> name + "[" + lhsName + "=Attribute[channel=0], " + rhsName + "=Attribute[channel=1]]",
-            (lhs, rhs) -> warnings,
+            warnings,
             suppliers,
             expectedType,
             symmetric
@@ -970,6 +994,12 @@ public static List<TypedDataSupplier> dateCases() {
                 // 2286-11-20T17:46:40Z - +292278994-08-17T07:12:55.807Z
                 () -> ESTestCase.randomLongBetween(10 * (long) 10e11, Long.MAX_VALUE),
                 DataTypes.DATETIME
+            ),
+            new TypedDataSupplier(
+                "<near the end of time>",
+                // very close to +292278994-08-17T07:12:55.807Z, the maximum supported millis since epoch
+                () -> ESTestCase.randomLongBetween(Long.MAX_VALUE / 100 * 99, Long.MAX_VALUE),
+                DataTypes.DATETIME
             )
         );
     }
diff --git a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/arithmetic/AddTests.java b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/arithmetic/AddTests.java
index 2596959c449db..2daf2688d6631 100644
--- a/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/arithmetic/AddTests.java
+++ b/x-pack/plugin/esql/src/test/java/org/elasticsearch/xpack/esql/expression/predicate/operator/arithmetic/AddTests.java
@@ -21,9 +21,12 @@
 import java.math.BigInteger;
 import java.time.Duration;
 import java.time.Period;
+import java.time.temporal.TemporalAmount;
 import java.util.ArrayList;
 import java.util.List;
 import java.util.Set;
+import java.util.function.BiFunction;
+import java.util.function.BinaryOperator;
 import java.util.function.Supplier;
 
 import static org.elasticsearch.xpack.esql.expression.predicate.operator.arithmetic.AbstractArithmeticTestCase.arithmeticExceptionOverflowCase;
@@ -116,29 +119,35 @@ public static Iterable<Object[]> parameters() {
             )
         );
 
+        BinaryOperator<Object> result = (lhs, rhs) -> {
+            try {
+                return addDatesAndTemporalAmount(lhs, rhs);
+            } catch (ArithmeticException e) {
+                return null;
+            }
+        };
+        BiFunction<TestCaseSupplier.TypedData, TestCaseSupplier.TypedData, List<String>> warnings = (lhs, rhs) -> {
+            try {
+                addDatesAndTemporalAmount(lhs.data(), rhs.data());
+                return List.of();
+            } catch (ArithmeticException e) {
+                return List.of(
+                    "Line -1:-1: evaluation of [] failed, treating result as null. Only first 20 failures recorded.",
+                    "Line -1:-1: java.lang.ArithmeticException: long overflow"
+                );
+            }
+        };
         suppliers.addAll(
             TestCaseSupplier.forBinaryNotCasting(
                 // TODO: There is an evaluator for Datetime + Period, so it should be tested. Similarly below.
                 "No evaluator, the tests only trigger the folding code since Period is not representable",
                 "lhs",
                 "rhs",
-                (lhs, rhs) -> {
-                    // this weird casting dance makes the expected value lambda symmetric
-                    Long date;
-                    Period period;
-                    if (lhs instanceof Long) {
-                        date = (Long) lhs;
-                        period = (Period) rhs;
-                    } else {
-                        date = (Long) rhs;
-                        period = (Period) lhs;
-                    }
-                    return asMillis(asDateTime(date).plus(period));
-                },
+                result,
                 DataTypes.DATETIME,
                 TestCaseSupplier.dateCases(),
                 TestCaseSupplier.datePeriodCases(),
-                List.of(),
+                warnings,
                 true
             )
         );
@@ -148,23 +157,11 @@ public static Iterable<Object[]> parameters() {
                 "No evaluator, the tests only trigger the folding code since Duration is not representable",
                 "lhs",
                 "rhs",
-                (lhs, rhs) -> {
-                    // this weird casting dance makes the expected value lambda symmetric
-                    Long date;
-                    Duration duration;
-                    if (lhs instanceof Long) {
-                        date = (Long) lhs;
-                        duration = (Duration) rhs;
-                    } else {
-                        date = (Long) rhs;
-                        duration = (Duration) lhs;
-                    }
-                    return asMillis(asDateTime(date).plus(duration));
-                },
+                result,
                 DataTypes.DATETIME,
                 TestCaseSupplier.dateCases(),
                 TestCaseSupplier.timeDurationCases(),
-                List.of(),
+                warnings,
                 true
             )
         );
@@ -269,6 +266,20 @@ private static String addErrorMessageString(boolean includeOrdinal, List<Set<Dat
         }
     }
 
+    private static Object addDatesAndTemporalAmount(Object lhs, Object rhs) {
+        // this weird casting dance makes the expected value lambda symmetric
+        Long date;
+        TemporalAmount period;
+        if (lhs instanceof Long) {
+            date = (Long) lhs;
+            period = (TemporalAmount) rhs;
+        } else {
+            date = (Long) rhs;
+            period = (TemporalAmount) lhs;
+        }
+        return asMillis(asDateTime(date).plus(period));
+    }
+
     @Override
     protected Expression build(Source source, List<Expression> args) {
         return new Add(source, args.get(0), args.get(1));