diff --git a/.github/workflows/NetCoreTests.yml b/.github/workflows/NetCoreTests.yml
index c88177b97e9..478eabf8f9a 100644
--- a/.github/workflows/NetCoreTests.yml
+++ b/.github/workflows/NetCoreTests.yml
@@ -12,6 +12,10 @@ jobs:
             CONNECTION_STRING: "Server=localhost;initial catalog=nhibernate;User Id=sa;Password=P@ssw0rd;packet size=4096;"
             DB_INIT: |
               docker run -e "ACCEPT_EULA=Y" -e "SA_PASSWORD=P@ssw0rd" -e "MSSQL_PID=Express" -p 1433:1433 -d --name sqlexpress mcr.microsoft.com/mssql/server:2019-latest;
+          - DB: SqlServer2008-MicrosoftDataSqlClientDriver
+            CONNECTION_STRING: "Server=localhost;initial catalog=nhibernate;User Id=sa;Password=P@ssw0rd;packet size=4096;"
+            DB_INIT: |
+              docker run -e "ACCEPT_EULA=Y" -e "SA_PASSWORD=P@ssw0rd" -e "MSSQL_PID=Express" -p 1433:1433 -d --name sqlexpress mcr.microsoft.com/mssql/server:2019-latest;
           - DB: PostgreSQL
             CONNECTION_STRING: "Host=localhost;Username=nhibernate;Password=nhibernate;Database=nhibernate;Enlist=true;"
             DB_INIT: |
diff --git a/appveyor.yml b/appveyor.yml
index a73e841f7e6..cf5da450722 100644
--- a/appveyor.yml
+++ b/appveyor.yml
@@ -4,6 +4,8 @@ environment:
   matrix:
   - DB: SqlServer2008
     CONNECTION_STRING: Server=(local)\SQL2017;User ID=sa;Password=Password12!;initial catalog=nhibernate;
+  - DB: SqlServer2008-MicrosoftDataSqlClientDriver
+    CONNECTION_STRING: Server=(local)\SQL2017;User ID=sa;Password=Password12!;initial catalog=nhibernate;
   - DB: PostgreSQL
     CONNECTION_STRING: Host=localhost;Port=5432;Username=postgres;Password=Password12!;Database=nhibernate;Enlist=true;
   - DB: Firebird
@@ -73,7 +75,9 @@ before_test:
         Start-Service 'postgresql-x64-10'
       }
       'SqlServer2008' { Start-Service 'MSSQL$SQL2017' }
+      'SqlServer2008-MicrosoftDataSqlClientDriver' { Start-Service 'MSSQL$SQL2017' }
       'SqlServer2012' { Start-Service 'MSSQL$SQL2017' }
+      'SqlServer2012-MicrosoftDataSqlClientDriver' { Start-Service 'MSSQL$SQL2017' }
       'SQLite' { }
     }
 test_script:
diff --git a/psake.ps1 b/psake.ps1
index 34fa3e2ea37..16f7a267f14 100644
--- a/psake.ps1
+++ b/psake.ps1
@@ -63,9 +63,22 @@ Task Set-Configuration {
         };
         'SqlServer2008' = @{
             'connection.connection_string' = 'Server=(local)\SQL2017;User ID=sa;Password=Password12!;initial catalog=nhibernate;'
+            'connection.driver_class' = 'NHibernate.Driver.Sql2008ClientDriver';
+            'dialect' = 'NHibernate.Dialect.MsSql2008Dialect'
         };
         'SqlServer2012' = @{
             'connection.connection_string' = 'Server=(local)\SQL2017;User ID=sa;Password=Password12!;initial catalog=nhibernate;';
+            'connection.driver_class' = 'NHibernate.Driver.Sql2008ClientDriver';
+            'dialect' = 'NHibernate.Dialect.MsSql2012Dialect'
+        };
+        'SqlServer2008-MicrosoftDataSqlClientDriver' = @{
+            'connection.connection_string' = 'Server=(local)\SQL2017;User ID=sa;Password=Password12!;initial catalog=nhibernate;'
+            'connection.driver_class' = 'NHibernate.Driver.MicrosoftDataSqlClientDriver';
+            'dialect' = 'NHibernate.Dialect.MsSql2008Dialect'
+        };
+        'SqlServer2012-MicrosoftDataSqlClientDriver' = @{
+            'connection.connection_string' = 'Server=(local)\SQL2017;User ID=sa;Password=Password12!;initial catalog=nhibernate;';
+            'connection.driver_class' = 'NHibernate.Driver.MicrosoftDataSqlClientDriver';
             'dialect' = 'NHibernate.Dialect.MsSql2012Dialect'
         };
         'Oracle' = @{
diff --git a/src/NHibernate.TestDatabaseSetup/TestDatabaseSetup.cs b/src/NHibernate.TestDatabaseSetup/TestDatabaseSetup.cs
index deea09fb3a5..0856f339d02 100644
--- a/src/NHibernate.TestDatabaseSetup/TestDatabaseSetup.cs
+++ b/src/NHibernate.TestDatabaseSetup/TestDatabaseSetup.cs
@@ -23,6 +23,7 @@ public class DatabaseSetup
 			{
 				{"NHibernate.Driver.SqlClientDriver", SetupSqlServer},
 				{"NHibernate.Driver.Sql2008ClientDriver", SetupSqlServer},
+				{"NHibernate.Driver.MicrosoftDataSqlClientDriver", SetupSqlServer},
 				{"NHibernate.Driver.FirebirdClientDriver", SetupFirebird},
 				{"NHibernate.Driver.NpgsqlDriver", SetupNpgsql},
 				{"NHibernate.Driver.OracleDataClientDriver", SetupOracle},
diff --git a/src/NHibernate/Driver/MicrosoftDataSqlClientDriver.cs b/src/NHibernate/Driver/MicrosoftDataSqlClientDriver.cs
index 1c4ad3d9fc0..e2e12674e3d 100644
--- a/src/NHibernate/Driver/MicrosoftDataSqlClientDriver.cs
+++ b/src/NHibernate/Driver/MicrosoftDataSqlClientDriver.cs
@@ -112,7 +112,7 @@ protected override void InitializeParameter(DbParameter dbParam, string name, Sq
 				case DbType.AnsiStringFixedLength:
 					dbParam.Size = IsAnsiText(dbParam, sqlType)
 						? MsSql2000Dialect.MaxSizeForAnsiClob
-						: MsSql2000Dialect.MaxSizeForLengthLimitedAnsiString;
+						: IsChar(dbParam, sqlType) ? sqlType.Length : MsSql2000Dialect.MaxSizeForLengthLimitedAnsiString;
 					break;
 				case DbType.Binary:
 					dbParam.Size = IsBlob(dbParam, sqlType)
@@ -130,7 +130,7 @@ protected override void InitializeParameter(DbParameter dbParam, string name, Sq
 				case DbType.StringFixedLength:
 					dbParam.Size = IsText(dbParam, sqlType)
 						? MsSql2000Dialect.MaxSizeForClob
-						: MsSql2000Dialect.MaxSizeForLengthLimitedString;
+						: IsChar(dbParam, sqlType) ? sqlType.Length : MsSql2000Dialect.MaxSizeForLengthLimitedString;
 					break;
 				case DbType.DateTime2:
 					dbParam.Size = MsSql2000Dialect.MaxDateTime2;
@@ -199,6 +199,18 @@ protected static bool IsBlob(DbParameter dbParam, SqlType sqlType)
 			return sqlType is BinaryBlobSqlType || DbType.Binary == dbParam.DbType && sqlType.LengthDefined &&
 			       sqlType.Length > MsSql2000Dialect.MaxSizeForLengthLimitedBinary;
 		}
+		
+		/// <summary>
+		/// Interprets if a parameter is a character (for the purposes of setting its default size)
+		/// </summary>
+		/// <param name="dbParam">The parameter</param>
+		/// <param name="sqlType">The <see cref="SqlType" /> of the parameter</param>
+		/// <returns>True, if the parameter should be interpreted as a character, otherwise False</returns>
+		protected static bool IsChar(DbParameter dbParam, SqlType sqlType)
+		{
+			return sqlType.LengthDefined && sqlType.Length == 1 &&
+			       (dbParam.DbType == DbType.StringFixedLength || dbParam.DbType == DbType.AnsiStringFixedLength);
+		}
 
 		/// <inheritdoc />
 		public override IResultSetsCommand GetResultSetsCommand(ISessionImplementor session)
diff --git a/src/NHibernate/Driver/SqlClientDriver.cs b/src/NHibernate/Driver/SqlClientDriver.cs
index 1002005395d..a3da3a4db73 100644
--- a/src/NHibernate/Driver/SqlClientDriver.cs
+++ b/src/NHibernate/Driver/SqlClientDriver.cs
@@ -295,8 +295,8 @@ protected static bool IsBlob(DbParameter dbParam, SqlType sqlType)
 		/// <returns>True, if the parameter should be interpreted as a character, otherwise False</returns>
 		protected static bool IsChar(DbParameter dbParam, SqlType sqlType)
 		{
-			return (DbType.StringFixedLength == dbParam.DbType || DbType.AnsiStringFixedLength == dbParam.DbType) &&
-			       sqlType.LengthDefined && sqlType.Length == 1;
+			return sqlType.LengthDefined && sqlType.Length == 1 &&
+			       (dbParam.DbType == DbType.StringFixedLength || dbParam.DbType == DbType.AnsiStringFixedLength);
 		}
 
 		public override IResultSetsCommand GetResultSetsCommand(ISessionImplementor session)
diff --git a/teamcity.build b/teamcity.build
index 7e90e13e430..b8125f5dfe5 100644
--- a/teamcity.build
+++ b/teamcity.build
@@ -67,11 +67,22 @@
 		<property name="nhibernate.connection.driver_class" value="NHibernate.Driver.Sql2008ClientDriver" />
 	</target>
 
+	<target name="setup-teamcity-sqlServer-MicrosoftDataSqlClientDriver">
+		<property name="db-service" value="MSSQL$SQLEXPRESS" />
+		<property name="nhibernate.connection.driver_class" value="NHibernate.Driver.MicrosoftDataSqlClientDriver" />
+	</target>
+
 	<target name="setup-teamcity-sqlServer2012">
 		<property name="db-service" value="MSSQL$SQLEXPRESS" />
 		<property name="nhibernate.dialect" value="NHibernate.Dialect.MsSql2012Dialect" />
 	</target>
 
+	<target name="setup-teamcity-sqlServer2012-MicrosoftDataSqlClientDriver">
+		<property name="db-service" value="MSSQL$SQLEXPRESS" />
+		<property name="nhibernate.dialect" value="NHibernate.Dialect.MsSql2012Dialect" />
+		<property name="nhibernate.connection.driver_class" value="NHibernate.Driver.MicrosoftDataSqlClientDriver" />
+	</target>
+
 	<target name="setup-teamcity-sqlServerCe32">
 		<property name="nhibernate.connection.driver_class" value="NHibernate.Driver.SqlServerCeDriver" />
 		<property name="nhibernate.dialect" value="NHibernate.Dialect.MsSqlCe40Dialect" />