diff --git a/src/EFCore.Cosmos/Query/Internal/SqlExpressionFactory.cs b/src/EFCore.Cosmos/Query/Internal/SqlExpressionFactory.cs
index 073a15175f1..61f8913a44e 100644
--- a/src/EFCore.Cosmos/Query/Internal/SqlExpressionFactory.cs
+++ b/src/EFCore.Cosmos/Query/Internal/SqlExpressionFactory.cs
@@ -106,6 +106,7 @@ private SqlExpression ApplyTypeMappingOnSqlUnary(
             SqlUnaryExpression sqlUnaryExpression, CoreTypeMapping typeMapping)
         {
             SqlExpression operand;
+            Type resultType;
             CoreTypeMapping resultTypeMapping;
             switch (sqlUnaryExpression.OperatorType)
             {
@@ -115,18 +116,23 @@ private SqlExpression ApplyTypeMappingOnSqlUnary(
                     when sqlUnaryExpression.IsLogicalNot():
                 {
                     resultTypeMapping = _boolTypeMapping;
+                    resultType = typeof(bool);
                     operand = ApplyDefaultTypeMapping(sqlUnaryExpression.Operand);
                     break;
                 }
 
                 case ExpressionType.Convert:
                     resultTypeMapping = typeMapping;
+                    // Since we are applying convert, resultTypeMapping decides the clrType
+                    resultType = resultTypeMapping?.ClrType ?? sqlUnaryExpression.Type;
                     operand = ApplyDefaultTypeMapping(sqlUnaryExpression.Operand);
                     break;
 
                 case ExpressionType.Not:
                 case ExpressionType.Negate:
                     resultTypeMapping = typeMapping;
+                    // While Not is logical, negate is numeric hence we use clrType from TypeMapping
+                    resultType = resultTypeMapping?.ClrType ?? sqlUnaryExpression.Type;
                     operand = ApplyTypeMapping(sqlUnaryExpression.Operand, typeMapping);
                     break;
 
@@ -134,11 +140,7 @@ when sqlUnaryExpression.IsLogicalNot():
                     throw new InvalidOperationException(CoreStrings.TranslationFailed(sqlUnaryExpression.Print()));
             }
 
-            return new SqlUnaryExpression(
-                sqlUnaryExpression.OperatorType,
-                operand,
-                sqlUnaryExpression.Type,
-                resultTypeMapping);
+            return new SqlUnaryExpression(sqlUnaryExpression.OperatorType, operand, resultType, resultTypeMapping);
         }
 
         private SqlExpression ApplyTypeMappingOnSqlBinary(
@@ -160,11 +162,14 @@ private SqlExpression ApplyTypeMappingOnSqlBinary(
                 case ExpressionType.NotEqual:
                 {
                     inferredTypeMapping = ExpressionExtensions.InferTypeMapping(left, right)
-                                          ?? _typeMappingSource.FindMapping(left.Type);
+                        // We avoid object here since the result does not get typeMapping from outside.
+                        ?? (left.Type != typeof(object)
+                            ? _typeMappingSource.FindMapping(left.Type)
+                            : _typeMappingSource.FindMapping(right.Type));
                     resultType = typeof(bool);
                     resultTypeMapping = _boolTypeMapping;
                 }
-                    break;
+                break;
 
                 case ExpressionType.AndAlso:
                 case ExpressionType.OrElse:
@@ -173,7 +178,7 @@ private SqlExpression ApplyTypeMappingOnSqlBinary(
                     resultType = typeof(bool);
                     resultTypeMapping = _boolTypeMapping;
                 }
-                    break;
+                break;
 
                 case ExpressionType.Add:
                 case ExpressionType.Subtract:
@@ -186,10 +191,10 @@ private SqlExpression ApplyTypeMappingOnSqlBinary(
                 case ExpressionType.Or:
                 {
                     inferredTypeMapping = typeMapping ?? ExpressionExtensions.InferTypeMapping(left, right);
-                    resultType = left.Type;
+                    resultType = inferredTypeMapping?.ClrType ?? left.Type;
                     resultTypeMapping = inferredTypeMapping;
                 }
-                    break;
+                break;
 
                 default:
                     throw new InvalidOperationException(CoreStrings.IncorrectOperatorType);
diff --git a/src/EFCore.Relational/Query/SqlExpressionFactory.cs b/src/EFCore.Relational/Query/SqlExpressionFactory.cs
index f247784b154..b064464fb19 100644
--- a/src/EFCore.Relational/Query/SqlExpressionFactory.cs
+++ b/src/EFCore.Relational/Query/SqlExpressionFactory.cs
@@ -106,6 +106,7 @@ private SqlExpression ApplyTypeMappingOnSqlUnary(
             SqlUnaryExpression sqlUnaryExpression, RelationalTypeMapping typeMapping)
         {
             SqlExpression operand;
+            Type resultType;
             RelationalTypeMapping resultTypeMapping;
             switch (sqlUnaryExpression.OperatorType)
             {
@@ -115,18 +116,23 @@ private SqlExpression ApplyTypeMappingOnSqlUnary(
                     when sqlUnaryExpression.IsLogicalNot():
                 {
                     resultTypeMapping = _boolTypeMapping;
+                    resultType = typeof(bool);
                     operand = ApplyDefaultTypeMapping(sqlUnaryExpression.Operand);
                     break;
                 }
 
                 case ExpressionType.Convert:
                     resultTypeMapping = typeMapping;
+                    // Since we are applying convert, resultTypeMapping decides the clrType
+                    resultType = resultTypeMapping?.ClrType ?? sqlUnaryExpression.Type;
                     operand = ApplyDefaultTypeMapping(sqlUnaryExpression.Operand);
                     break;
 
                 case ExpressionType.Not:
                 case ExpressionType.Negate:
                     resultTypeMapping = typeMapping;
+                    // While Not is logical, negate is numeric hence we use clrType from TypeMapping
+                    resultType = resultTypeMapping?.ClrType ?? sqlUnaryExpression.Type;
                     operand = ApplyTypeMapping(sqlUnaryExpression.Operand, typeMapping);
                     break;
 
@@ -134,11 +140,7 @@ when sqlUnaryExpression.IsLogicalNot():
                     throw new InvalidOperationException(CoreStrings.UnsupportedUnary);
             }
 
-            return new SqlUnaryExpression(
-                sqlUnaryExpression.OperatorType,
-                operand,
-                sqlUnaryExpression.Type,
-                resultTypeMapping);
+            return new SqlUnaryExpression(sqlUnaryExpression.OperatorType, operand, resultType, resultTypeMapping);
         }
 
         private SqlExpression ApplyTypeMappingOnSqlBinary(
@@ -160,7 +162,10 @@ private SqlExpression ApplyTypeMappingOnSqlBinary(
                 case ExpressionType.NotEqual:
                 {
                     inferredTypeMapping = ExpressionExtensions.InferTypeMapping(left, right)
-                        ?? _typeMappingSource.FindMapping(left.Type);
+                        // We avoid object here since the result does not get typeMapping from outside.
+                        ?? (left.Type != typeof(object)
+                            ? _typeMappingSource.FindMapping(left.Type)
+                            : _typeMappingSource.FindMapping(right.Type));
                     resultType = typeof(bool);
                     resultTypeMapping = _boolTypeMapping;
                     break;
@@ -184,7 +189,7 @@ private SqlExpression ApplyTypeMappingOnSqlBinary(
                 case ExpressionType.Or:
                 {
                     inferredTypeMapping = typeMapping ?? ExpressionExtensions.InferTypeMapping(left, right);
-                    resultType = left.Type;
+                    resultType = inferredTypeMapping?.ClrType ?? left.Type;
                     resultTypeMapping = inferredTypeMapping;
                     break;
                 }
@@ -437,7 +442,10 @@ public virtual CaseExpression Case(
 
             var operandTypeMapping = operand.TypeMapping
                 ?? whenClauses.Select(wc => wc.Test.TypeMapping).FirstOrDefault(t => t != null)
-                ?? _typeMappingSource.FindMapping(operand.Type);
+                // Since we never look at type of Operand/Test after this place,
+                // we need to find actual typeMapping based on non-object type.
+                ?? new[] { operand.Type }.Concat(whenClauses.Select(wc => wc.Test.Type))
+                    .Where(t => t != typeof(object)).Select(t => _typeMappingSource.FindMapping(t)).FirstOrDefault();
 
             var resultTypeMapping = elseResult?.TypeMapping
                 ?? whenClauses.Select(wc => wc.Result.TypeMapping).FirstOrDefault(t => t != null);
diff --git a/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindMiscellaneousQuerySqlServerTest.cs b/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindMiscellaneousQuerySqlServerTest.cs
index a73af113a20..e327a278972 100644
--- a/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindMiscellaneousQuerySqlServerTest.cs
+++ b/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindMiscellaneousQuerySqlServerTest.cs
@@ -2778,7 +2778,7 @@ public override async Task Concat_string_int(bool async)
             await base.Concat_string_int(async);
 
             AssertSql(
-                @"SELECT CAST([o].[OrderID] AS nchar(5)) + [o].[CustomerID]
+                @"SELECT CAST([o].[OrderID] AS nchar(5)) + COALESCE([o].[CustomerID], N'')
 FROM [Orders] AS [o]");
         }
 
diff --git a/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindWhereQuerySqlServerTest.cs b/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindWhereQuerySqlServerTest.cs
index b2b83825c55..10f220cc74d 100644
--- a/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindWhereQuerySqlServerTest.cs
+++ b/test/EFCore.SqlServer.FunctionalTests/Query/NorthwindWhereQuerySqlServerTest.cs
@@ -1341,7 +1341,7 @@ public override async Task Where_concat_string_int_comparison4(bool async)
             AssertSql(
                 @"SELECT [o].[CustomerID]
 FROM [Orders] AS [o]
-WHERE ((CAST([o].[OrderID] AS nchar(5)) + [o].[CustomerID]) = [o].[CustomerID]) OR [o].[CustomerID] IS NULL");
+WHERE (CAST([o].[OrderID] AS nchar(5)) + COALESCE([o].[CustomerID], N'')) = [o].[CustomerID]");
         }
 
         public override async Task Where_concat_string_string_comparison(bool async)
diff --git a/test/EFCore.Sqlite.FunctionalTests/Query/NorthwindMiscellaneousQuerySqliteTest.cs b/test/EFCore.Sqlite.FunctionalTests/Query/NorthwindMiscellaneousQuerySqliteTest.cs
index 321c9f0d37d..b20dd511cc2 100644
--- a/test/EFCore.Sqlite.FunctionalTests/Query/NorthwindMiscellaneousQuerySqliteTest.cs
+++ b/test/EFCore.Sqlite.FunctionalTests/Query/NorthwindMiscellaneousQuerySqliteTest.cs
@@ -242,10 +242,13 @@ public override Task Complex_nested_query_doesnt_try_binding_to_grandparent_when
 
         public override Task AsQueryable_in_query_server_evals(bool async) => null;
 
-        [ConditionalTheory(Skip = "Issue #19990")]
         public override async Task Concat_string_int(bool async)
         {
             await base.Concat_string_int(async);
+
+            AssertSql(
+                @"SELECT CAST(""o"".""OrderID"" AS TEXT) || COALESCE(""o"".""CustomerID"", '')
+FROM ""Orders"" AS ""o""");
         }
 
         public override async Task Concat_int_string(bool async)