To reproduce: this.radDateTimePicker1.Format = DateTimePickerFormat.Short; this.radDateTimePicker1.Value = new DateTime(2016, 5, 12); this.radTextBox1.Text = "9/5/2016"; Second scenario: this.radDateTimePicker1.Format = DateTimePickerFormat.Short; If you copy "1/7/16" and paste it into RadDateTimeicker, the result date will be "1/7/1616". In the previous version, the result was correct 1/7/2016. Copy the value in the text box and paste it in RadDateTimePicker. Workaround: public Form1() { InitializeComponent(); this.radDateTimePicker1.Format = DateTimePickerFormat.Short; this.radDateTimePicker1.Value = new DateTime(2016, 5, 12); this.radTextBox1.Text = "9/5/2016"; this.radDateTimePicker1.ValueChanging += radDateTimePicker1_ValueChanging; this.radDateTimePicker1.DateTimePickerElement.TextBoxElement.TextBoxItem.TextBoxControl.KeyPress += TextBoxControl_KeyPress; } string clipboardData; private void TextBoxControl_KeyPress(object sender, KeyPressEventArgs e) { if (e.KeyChar == '\x16') { if (clipboardData != null) { this.radDateTimePicker1.Text = clipboardData; clipboardData = null; } } } private void radDateTimePicker1_ValueChanging(object sender, Telerik.WinControls.UI.ValueChangingEventArgs e) { if (clipboardData == null) { clipboardData = RadMaskedEditBoxElement.GetClipboardText(); } }