diff --git a/Frameworks/PlugIns/ERMicrosoftPlugIn/Sources/com/webobjects/jdbcadaptor/ERMicrosoftExpression.java b/Frameworks/PlugIns/ERMicrosoftPlugIn/Sources/com/webobjects/jdbcadaptor/ERMicrosoftExpression.java
new file mode 100644
index 0000000000..6a672e07d5
--- /dev/null
+++ b/Frameworks/PlugIns/ERMicrosoftPlugIn/Sources/com/webobjects/jdbcadaptor/ERMicrosoftExpression.java
@@ -0,0 +1,69 @@
+package com.webobjects.jdbcadaptor;
+
+import com.webobjects.eoaccess.EOAttribute;
+import com.webobjects.eoaccess.EOEntity;
+import com.webobjects.foundation.NSMutableDictionary;
+import com.webobjects.foundation.NSTimestamp;
+import com.webobjects.foundation.NSTimestampFormatter;
+
+import java.sql.Timestamp;
+
+/**
+ * Overrides {@code MicrosoftExpression} in order to add TIMESTAMP values including milliseconds.
+ *
+ * @author hprange (most code was copied from {@code EROracleExpression})
+ */
+public class ERMicrosoftExpression extends MicrosoftPlugIn.MicrosoftExpression {
+    private static final NSTimestampFormatter _TIMESTAMP_FORMATTER = new NSTimestampFormatter("%Y-%m-%d %H:%M:%S.%F");
+
+    public ERMicrosoftExpression(EOEntity entity) {
+        super(entity);
+    }
+
+    /**
+     * Overridden in order to add milliseconds to the value. This applies only if value is an instance of
+     * {@code NSTimestamp} and if valueType from the attribute is {@code 'T'}.
+     *
+     * @param attribute the EOAttribute associated with the bind variable dictionary
+     * @param value     the value associated with the bind variable dictionary
+     * @return the modified bind variable dictionary for {@code attribute} and {@code value}
+     */
+    @Override
+    public NSMutableDictionary<String, Object> bindVariableDictionaryForAttribute(EOAttribute attribute, Object value) {
+        NSMutableDictionary<String, Object> result = super.bindVariableDictionaryForAttribute(attribute, value);
+
+        if (value instanceof NSTimestamp && isTimestampAttribute(attribute)) {
+            NSTimestamp nstimestamp = (NSTimestamp) value;
+            long millis = nstimestamp.getTime();
+            // AK: since NSTimestamp places fractional millis in the getTime,
+            // the driver is getting very confused and refuses to update the columns as
+            // they get translated to 0 as the fractional values.
+            Timestamp timestamp = new Timestamp(millis);
+            timestamp.setNanos(timestamp.getNanos() + nstimestamp.getNanos());
+            result.setObjectForKey(timestamp, "BindVariableValue");
+        }
+
+        return result;
+    }
+
+    /**
+     * Overridden to add milliseconds to the value. This applies only if value is an instance of {@code NSTimestamp} and
+     * if valueType from the attribute is {@code T}.
+     *
+     * @param value     an object to be used in a SQL statement
+     * @param attribute an EOAttribute to be used in influencing the format
+     * @return the modified formatted string
+     */
+    @Override
+    public String formatValueForAttribute(Object value, EOAttribute attribute) {
+        if (value instanceof NSTimestamp && isTimestampAttribute(attribute)) {
+            return "'" + _TIMESTAMP_FORMATTER.format(value) + "'";
+        }
+
+        return super.formatValueForAttribute(value, attribute);
+    }
+
+    private boolean isTimestampAttribute(EOAttribute attribute) {
+        return "T".equals(attribute.valueType());
+    }
+}
diff --git a/Frameworks/PlugIns/ERMicrosoftPlugIn/Sources/com/webobjects/jdbcadaptor/ERMicrosoftPlugIn.java b/Frameworks/PlugIns/ERMicrosoftPlugIn/Sources/com/webobjects/jdbcadaptor/ERMicrosoftPlugIn.java
index d669f29783..39c0913bde 100644
--- a/Frameworks/PlugIns/ERMicrosoftPlugIn/Sources/com/webobjects/jdbcadaptor/ERMicrosoftPlugIn.java
+++ b/Frameworks/PlugIns/ERMicrosoftPlugIn/Sources/com/webobjects/jdbcadaptor/ERMicrosoftPlugIn.java
@@ -59,6 +59,14 @@ public String defaultDriverName() {
         return "com.microsoft.sqlserver.jdbc.SQLServerDriver";
     }
 
+    /**
+     * Uses the enhanced {@code ERMicrosoftExpression} as the expression class.
+     */
+    @Override
+    public Class defaultExpressionClass() {
+        return ERMicrosoftExpression.class;
+    }
+
     /**
      * Generates a batch of new primary keys for the given entity. Overrides the default implementation to provide a
      * more efficient mechanism for generating primary keys using database sequences.