diff --git a/src/EFCore.Sqlite.Core/Query/Internal/SqliteMethodCallTranslatorProvider.cs b/src/EFCore.Sqlite.Core/Query/Internal/SqliteMethodCallTranslatorProvider.cs
index f35640cacc7..9f1660c5a0c 100644
--- a/src/EFCore.Sqlite.Core/Query/Internal/SqliteMethodCallTranslatorProvider.cs
+++ b/src/EFCore.Sqlite.Core/Query/Internal/SqliteMethodCallTranslatorProvider.cs
@@ -31,7 +31,7 @@ public SqliteMethodCallTranslatorProvider([NotNull] RelationalMethodCallTranslat
                     new SqliteByteArrayMethodTranslator(sqlExpressionFactory),
                     new SqliteDateTimeAddTranslator(sqlExpressionFactory),
                     new SqliteMathTranslator(sqlExpressionFactory),
-                    new SqliteRegexTranslator(sqlExpressionFactory),
+                    new SqliteRegexMethodTranslator(sqlExpressionFactory),
                     new SqliteStringMethodTranslator(sqlExpressionFactory)
                 });
         }
diff --git a/src/EFCore.Sqlite.Core/Query/Internal/SqliteRegexTranslator.cs b/src/EFCore.Sqlite.Core/Query/Internal/SqliteRegexMethodTranslator.cs
similarity index 78%
rename from src/EFCore.Sqlite.Core/Query/Internal/SqliteRegexTranslator.cs
rename to src/EFCore.Sqlite.Core/Query/Internal/SqliteRegexMethodTranslator.cs
index 8fee6f50889..29ed462f610 100644
--- a/src/EFCore.Sqlite.Core/Query/Internal/SqliteRegexTranslator.cs
+++ b/src/EFCore.Sqlite.Core/Query/Internal/SqliteRegexMethodTranslator.cs
@@ -19,10 +19,12 @@ namespace Microsoft.EntityFrameworkCore.Sqlite.Query.Internal
     ///     any release. You should only use it directly in your code with extreme caution and knowing that
     ///     doing so can result in application failures when updating to a new Entity Framework Core release.
     /// </summary>
-    public class SqliteRegexTranslator : IMethodCallTranslator
+    public class SqliteRegexMethodTranslator : IMethodCallTranslator
     {
+        private readonly static MethodInfo _regexIsMatchMethodInfo
+            = typeof(Regex).GetRuntimeMethod(nameof(Regex.IsMatch), new Type[] { typeof(string), typeof(string) });
+
         private readonly ISqlExpressionFactory _sqlExpressionFactory;
-        private readonly static MethodInfo regexIsMatchMethod = typeof(Regex).GetMethod(nameof(Regex.IsMatch), new Type[] { typeof(string), typeof(string) });
 
         /// <summary>
         ///     This is an internal API that supports the Entity Framework Core infrastructure and not subject to
@@ -30,17 +32,21 @@ public class SqliteRegexTranslator : IMethodCallTranslator
         ///     any release. You should only use it directly in your code with extreme caution and knowing that
         ///     doing so can result in application failures when updating to a new Entity Framework Core release.
         /// </summary>
-        public SqliteRegexTranslator([NotNull] ISqlExpressionFactory sqlExpressionFactory)
+        public SqliteRegexMethodTranslator([NotNull] ISqlExpressionFactory sqlExpressionFactory)
         {
+            Check.NotNull(sqlExpressionFactory, nameof(sqlExpressionFactory));
+
             _sqlExpressionFactory = sqlExpressionFactory;
         }
+
         /// <summary>
         ///     This is an internal API that supports the Entity Framework Core infrastructure and not subject to
         ///     the same compatibility standards as public APIs. It may be changed or removed without notice in
         ///     any release. You should only use it directly in your code with extreme caution and knowing that
         ///     doing so can result in application failures when updating to a new Entity Framework Core release.
         /// </summary>
-        public virtual SqlExpression Translate(SqlExpression instance,
+        public virtual SqlExpression Translate(
+            SqlExpression instance,
             MethodInfo method,
             IReadOnlyList<SqlExpression> arguments,
             IDiagnosticsLogger<DbLoggerCategory.Query> logger)
@@ -49,13 +55,13 @@ public virtual SqlExpression Translate(SqlExpression instance,
             Check.NotNull(arguments, nameof(arguments));
             Check.NotNull(logger, nameof(logger));
 
-
-            if (method.Equals(regexIsMatchMethod))
+            if (method.Equals(_regexIsMatchMethodInfo))
             {
-                return _sqlExpressionFactory.Function("regexp",
+                return _sqlExpressionFactory.Function(
+                    "regexp",
                     new[] { arguments[1], arguments[0] },
-                    false,
-                    new[] { false, false },
+                    nullable: true,
+                    argumentsPropagateNullability: new[] { true, true },
                     typeof(bool),
                     arguments[0].TypeMapping);
             }
diff --git a/src/EFCore.Sqlite.Core/Storage/Internal/SqliteRelationalConnection.cs b/src/EFCore.Sqlite.Core/Storage/Internal/SqliteRelationalConnection.cs
index a78fce5a056..1d32e86e7fc 100644
--- a/src/EFCore.Sqlite.Core/Storage/Internal/SqliteRelationalConnection.cs
+++ b/src/EFCore.Sqlite.Core/Storage/Internal/SqliteRelationalConnection.cs
@@ -115,13 +115,14 @@ private void InitializeDbConnection(DbConnection connection)
                     sqliteConnection.DefaultTimeout = _commandTimeout.Value;
                 }
 
-                sqliteConnection.CreateFunction<string, string, bool>(
+                sqliteConnection.CreateFunction<string, string, bool?>(
                     "regexp",
                     (pattern, input) =>
                     {
-                        if (input == null || pattern == null)
+                        if (input == null
+                            || pattern == null)
                         {
-                            return false;
+                            return null;
                         }
 
                         return Regex.IsMatch(input, pattern);
@@ -146,7 +147,8 @@ private void InitializeDbConnection(DbConnection connection)
 
                         return Convert.ToDouble(dividend, CultureInfo.InvariantCulture)
                             % Convert.ToDouble(divisor, CultureInfo.InvariantCulture);
-                    });
+                    },
+                    isDeterministic: true);
 
                 sqliteConnection.CreateFunction(
                     name: "ef_add",
@@ -176,7 +178,6 @@ private void InitializeDbConnection(DbConnection connection)
                     isDeterministic: true);
             }
             else
-
             {
                 _logger.UnexpectedConnectionTypeWarning(connection.GetType());
             }
diff --git a/test/EFCore.Cosmos.FunctionalTests/Query/NorthwindFunctionsQueryCosmosTest.cs b/test/EFCore.Cosmos.FunctionalTests/Query/NorthwindFunctionsQueryCosmosTest.cs
index 5937253d50f..5452c1928f8 100644
--- a/test/EFCore.Cosmos.FunctionalTests/Query/NorthwindFunctionsQueryCosmosTest.cs
+++ b/test/EFCore.Cosmos.FunctionalTests/Query/NorthwindFunctionsQueryCosmosTest.cs
@@ -1049,6 +1049,11 @@ public override Task Int_Compare_to_simple_zero(bool async)
             return base.Int_Compare_to_simple_zero(async);
         }
 
+        public override Task Regex_IsMatch_MethodCall(bool async)
+        {
+            return AssertTranslationFailed(() => base.Regex_IsMatch_MethodCall(async));
+        }
+
         private void AssertSql(params string[] expected)
             => Fixture.TestSqlLoggerFactory.AssertBaseline(expected);
 
diff --git a/test/EFCore.Specification.Tests/Query/NorthwindFunctionsQueryTestBase.cs b/test/EFCore.Specification.Tests/Query/NorthwindFunctionsQueryTestBase.cs
index 52788059cd2..57b86da8d3f 100644
--- a/test/EFCore.Specification.Tests/Query/NorthwindFunctionsQueryTestBase.cs
+++ b/test/EFCore.Specification.Tests/Query/NorthwindFunctionsQueryTestBase.cs
@@ -1590,7 +1590,8 @@ public virtual Task Projecting_Math_Truncate_and_ordering_by_it_twice3(bool asyn
         [MemberData(nameof(IsAsyncData))]
         public virtual Task Regex_IsMatch_MethodCall(bool async)
         {
-            return AssertQuery(async,
+            return AssertQuery(
+                async,
                 ss => ss.Set<Customer>().Where(o => Regex.IsMatch(o.CustomerID, @"^T")),
                 entryCount: 6);
         }
diff --git a/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindFunctionsQuerySqlServerTest.cs b/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindFunctionsQuerySqlServerTest.cs
index 130c6256bbc..630e0e6b822 100644
--- a/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindFunctionsQuerySqlServerTest.cs
+++ b/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindFunctionsQuerySqlServerTest.cs
@@ -1548,6 +1548,7 @@ public override async Task Projecting_Math_Truncate_and_ordering_by_it_twice3(bo
             //WHERE [o].[OrderID] < 10250
             //ORDER BY [A] DESC");
         }
+
         public override Task Regex_IsMatch_MethodCall(bool async)
         {
             return AssertTranslationFailed(() => base.Regex_IsMatch_MethodCall(async));