diff --git a/source/shared/core_stmt.cpp b/source/shared/core_stmt.cpp
index 649e1c3d..f88f6fc7 100644
--- a/source/shared/core_stmt.cpp
+++ b/source/shared/core_stmt.cpp
@@ -748,10 +748,14 @@ void core_sqlsrv_bind_param( _Inout_ sqlsrv_stmt* stmt, _In_ SQLUSMALLINT param_
 
     core::SQLBindParameter( stmt, param_num + 1, direction,
         c_type, sql_type, column_size, decimal_digits, buffer, buffer_len, &ind_ptr );
-    if ( stmt->conn->ce_option.enabled && sql_type == SQL_TYPE_TIMESTAMP )
-    {
-        if( decimal_digits == 3 )
-            core::SQLSetDescField( stmt, param_num + 1, SQL_CA_SS_SERVER_TYPE, (SQLPOINTER)SQL_SS_TYPE_DATETIME, SQL_IS_INTEGER );
+
+    // When calling SQLDescribeParam() on a parameter targeting a Datetime column, the return values for ParameterType, ColumnSize and DecimalDigits are SQL_TYPE_TIMESTAMP, 23, and 3 respectively.
+    // For a parameter targeting a SmallDatetime column, the return values are SQL_TYPE_TIMESTAMP, 16, and 0. Inputting these values into SQLBindParameter() results in Operand type clash error.
+    // This is because SQL_TYPE_TIMESTAMP corresponds to Datetime2 by default, and conversion of Datetime2 to Datetime and conversion of Datetime2 to SmallDatatime is not allowed with encrypted columns.
+    // To fix the conversion problem, set the SQL_CA_SS_SERVER_TYPE field of the parameter to SQL_SS_TYPE_DATETIME and SQL_SS_TYPE_SMALLDATETIME respectively for a Datetime and Smalldatetime column.
+    if (stmt->conn->ce_option.enabled && sql_type == SQL_TYPE_TIMESTAMP) {
+        if (decimal_digits == 3)
+            core::SQLSetDescField(stmt, param_num + 1, SQL_CA_SS_SERVER_TYPE, (SQLPOINTER)SQL_SS_TYPE_DATETIME, SQL_IS_INTEGER);
         else if (decimal_digits == 0)
             core::SQLSetDescField( stmt, param_num + 1, SQL_CA_SS_SERVER_TYPE, (SQLPOINTER)SQL_SS_TYPE_SMALLDATETIME, SQL_IS_INTEGER );
     }
diff --git a/test/functional/pdo_sqlsrv/pdo_ae_insert_datetime_encrypted.phpt b/test/functional/pdo_sqlsrv/pdo_ae_insert_datetime_encrypted.phpt
new file mode 100644
index 00000000..5d84a1d6
--- /dev/null
+++ b/test/functional/pdo_sqlsrv/pdo_ae_insert_datetime_encrypted.phpt
@@ -0,0 +1,139 @@
+--TEST--
+Test for inserting and retrieving encrypted data of datetime and smalldatetime types encrypted
+--DESCRIPTION--
+Verify that inserting into smalldatetime column might trigger "Datetime field overflow" error
+--SKIPIF--
+<?php require('skipif_mid-refactor.inc'); ?>
+--FILE--
+<?php
+require_once("MsSetup.inc");
+require_once("MsCommon_mid-refactor.inc");
+
+function getColDef($name, $type)
+{
+    $append = " ENCRYPTED WITH (ENCRYPTION_TYPE = deterministic, ALGORITHM = 'AEAD_AES_256_CBC_HMAC_SHA_256', COLUMN_ENCRYPTION_KEY = AEColumnKey) ";
+
+    $colDef = '[' . $name . '] ' . $type . $append;
+    return $colDef;
+}
+
+function createTableEncryptedQuery($conn, $tableName, $columns)
+{
+    $tsql = "CREATE TABLE $tableName (";
+    foreach ($columns as $name => $type) {
+        $colDef = getColDef($name, $type) . ', ';
+        $tsql .= $colDef;
+    }
+
+    $tsql = rtrim($tsql, ', ') . ')';
+    return $tsql;
+
+}
+
+function createTablePlainQuery($conn, $tableName, $columns)
+{
+    $tsql = "CREATE TABLE $tableName (";
+    foreach ($columns as $name => $type) {
+        $colDef = '[' . $name . '] ' . $type . ', ';
+        $tsql .= $colDef;
+    }
+
+    $tsql = rtrim($tsql, ', ') . ')';
+    return $tsql;
+}
+
+try {
+    // This test requires to connect with the Always Encrypted feature
+    // First check if the system is qualified to run this test
+    $dsn = getDSN($server, null);
+    $conn = new PDO($dsn, $uid, $pwd);
+    $qualified = isAEQualified($conn) && (strtoupper(substr(PHP_OS, 0, 3)) === 'WIN');
+
+    if ($qualified) {
+        unset($conn);
+
+        // Now connect with ColumnEncryption enabled
+        $connectionInfo = "ColumnEncryption = Enabled;";
+        $conn = new PDO("sqlsrv:server = $server; database=$databaseName; $connectionInfo", $uid, $pwd);
+    }
+
+    $conn->setAttribute(PDO::ATTR_ERRMODE, PDO::ERRMODE_EXCEPTION);
+
+    $tableName = 'pdo_datetime_encrypted';
+    dropTable($conn, $tableName);
+    
+    // Define the column definitions
+    $columns = array('c1' => 'smalldatetime', 'c2' => 'datetime', 'c3' => 'datetime2(4)');
+
+    if ($qualified) {
+        $tsql = createTableEncryptedQuery($conn, $tableName, $columns);
+    } else {
+        $tsql = createTablePlainQuery($conn, $tableName, $columns);
+    }
+    $conn->exec($tsql);
+    
+    // Insert values that cause errors
+    $val1 = '9999-12-31 23:59:59';
+    $val2 = null;
+    $val3 = '9999-12-31 23:59:59.9999';
+
+    $tsql = "INSERT INTO $tableName (c1, c2, c3) VALUES (?,?,?)";
+    $stmt = $conn->prepare($tsql);
+
+    $stmt->bindParam(1, $val1);
+    $stmt->bindParam(2, $val2);
+    $stmt->bindParam(3, $val3);
+    
+    try {
+        $stmt->execute();
+    } catch (PDOException $e) {
+        $error = ($qualified)? '*Datetime field overflow' : '*The conversion of a nvarchar data type to a smalldatetime data type resulted in an out-of-range value.';
+        if (!fnmatch($error, $e->getMessage())) {
+            echo "The error message is unexpected:\n";
+            var_dump($e->getMessage());
+        }
+    }
+    
+    // These values should work
+    $val1 = '2021-11-03 11:49:00';
+    $val2 = '2015-10-23 07:03:00.000';
+    
+    try {
+        $stmt->execute();
+    } catch (PDOException $e) {
+        echo "Errors unexpected!!\n";
+        var_dump($e->getMessage());
+    }
+  
+    unset($stmt);
+    
+    // Now fetch the values
+    $tsql = "SELECT * FROM $tableName";
+    
+    $stmt = $conn->prepare($tsql);
+    $stmt->execute();
+
+    $row = $stmt->fetch(PDO::FETCH_NUM);
+    var_dump($row);
+    
+    dropTable($conn, $tableName);
+
+    unset($stmt);
+    unset($conn);
+} catch (PDOException $e) {
+    echo $e->getMessage();
+}
+
+echo "Done\n";
+
+?>
+--EXPECT--
+array(3) {
+  [0]=>
+  string(19) "2021-11-03 11:49:00"
+  [1]=>
+  string(23) "2015-10-23 07:03:00.000"
+  [2]=>
+  string(24) "9999-12-31 23:59:59.9999"
+}
+Done
\ No newline at end of file
diff --git a/test/functional/sqlsrv/sqlsrv_ae_insert_datetime_encrypted.phpt b/test/functional/sqlsrv/sqlsrv_ae_insert_datetime_encrypted.phpt
new file mode 100644
index 00000000..8527d861
--- /dev/null
+++ b/test/functional/sqlsrv/sqlsrv_ae_insert_datetime_encrypted.phpt
@@ -0,0 +1,149 @@
+--TEST--
+Test for inserting and retrieving encrypted data of datetime and smalldatetime types encrypted
+--DESCRIPTION--
+Verify that inserting into smalldatetime column might trigger "Datetime field overflow" error
+--SKIPIF--
+<?php require('skipif.inc'); ?>
+--FILE--
+<?php
+    function getColDef($name, $type)
+    {
+        $append = " ENCRYPTED WITH (ENCRYPTION_TYPE = deterministic, ALGORITHM = 'AEAD_AES_256_CBC_HMAC_SHA_256', COLUMN_ENCRYPTION_KEY = AEColumnKey) ";
+
+        $colDef = '[' . $name . '] ' . $type . $append;
+        return $colDef;
+    }
+
+    function createTableEncryptedQuery($conn, $tableName, $columns)
+    {
+        $tsql = "CREATE TABLE $tableName (";
+        foreach ($columns as $name => $type) {
+            $colDef = getColDef($name, $type) . ', ';
+            $tsql .= $colDef;
+        }
+
+        $tsql = rtrim($tsql, ', ') . ')';
+        return $tsql;
+
+    }
+
+    function createTablePlainQuery($conn, $tableName, $columns)
+    {
+        $tsql = "CREATE TABLE $tableName (";
+        foreach ($columns as $name => $type) {
+            $colDef = '[' . $name . '] ' . $type . ', ';
+            $tsql .= $colDef;
+        }
+
+        $tsql = rtrim($tsql, ', ') . ')';
+        return $tsql;
+    }
+    
+    require_once("MsCommon.inc");
+
+    // This test requires to connect with the Always Encrypted feature
+    // First check if the system is qualified to run this test
+    $options = array('Database' => $database, 'UID' => $userName, 'PWD' => $userPassword, 'ReturnDatesAsStrings' => true);
+    $conn = sqlsrv_connect($server, $options);
+    if ($conn === false) {
+        fatalError("Failed to connect to $server.");
+    }
+
+    $qualified = AE\isQualified($conn) && (strtoupper(substr(PHP_OS, 0, 3)) === 'WIN');
+    if ($qualified) {
+        sqlsrv_close($conn);
+
+        // Now connect with ColumnEncryption enabled
+        $connectionOptions = array_merge($options, array('ColumnEncryption' => 'Enabled'));
+        $conn = sqlsrv_connect($server, $connectionOptions);
+        if ($conn === false) {
+            fatalError("Failed to connect to $server.");
+        }
+    }
+
+    $tableName = 'srv_datetime_encrypted';
+    dropTable($conn, $tableName);
+    
+    // Define the column definitions
+    $columns = array('c1' => 'smalldatetime', 'c2' => 'datetime', 'c3' => 'datetime2(4)');
+
+    if ($qualified) {
+        $tsql = createTableEncryptedQuery($conn, $tableName, $columns);
+    } else {
+        $tsql = createTablePlainQuery($conn, $tableName, $columns);
+    }
+    
+    $stmt = sqlsrv_query($conn, $tsql);
+    if (!$stmt) {
+        fatalError("Failed to create table $tableName\n");
+    }
+
+    // Insert values that cause errors
+    $val1 = '9999-12-31 23:59:59';
+    $val2 = null;
+    $val3 = '9999-12-31 23:59:59.9999';
+
+    $tsql = "INSERT INTO $tableName (c1, c2, c3) VALUES (?,?,?)";
+    $params = array($val1, $val2, $val3);
+
+    $stmt = sqlsrv_prepare($conn, $tsql, $params);
+    if (!$stmt) {
+        fatalError("Failed to prepare insert statement");
+    }
+    $result = sqlsrv_execute($stmt);
+    if ($result) {
+        echo "Inserting invalid values should have failed!\n";
+    } else {
+        $error = ($qualified)? '*Datetime field overflow' : '*The conversion of a varchar data type to a smalldatetime data type resulted in an out-of-range value.';
+        if (!fnmatch($error, sqlsrv_errors()[0]['message'])) {
+            var_dump(sqlsrv_errors());
+        }
+    }
+    
+    sqlsrv_free_stmt($stmt);
+
+    // These values should work
+    $val1 = '2021-11-03 11:49:00';
+    $val2 = '2015-10-23 07:03:00.000';
+
+    $params = array($val1, $val2, $val3);
+    $stmt = sqlsrv_prepare($conn, $tsql, $params);
+    if (!$stmt) {
+        fatalError("Failed to prepare insert statement");
+    }
+    $result = sqlsrv_execute($stmt);
+    if (!$result) {
+        fatalError("Failed to insert valid values\n");
+    }
+
+    sqlsrv_free_stmt($stmt);
+
+    // Now fetch the values
+    $tsql = "SELECT * FROM $tableName";
+    
+    $stmt = sqlsrv_query($conn, $tsql);
+    if (!$stmt) {
+        fatalError("Failed to select from $tableName");
+    }
+
+    $row = sqlsrv_fetch_array($stmt, SQLSRV_FETCH_ASSOC);
+    var_dump($row);
+
+    dropTable($conn, $tableName);
+
+    sqlsrv_free_stmt($stmt);
+    sqlsrv_close($conn);
+
+    echo "Done\n";
+
+?>
+--EXPECT--
+array(3) {
+  ["c1"]=>
+  string(19) "2021-11-03 11:49:00"
+  ["c2"]=>
+  string(23) "2015-10-23 07:03:00.000"
+  ["c3"]=>
+  string(24) "9999-12-31 23:59:59.9999"
+}
+Done