Hi Andreas,
Only 1 prompt is display because currently the user can enter 1 or 2 digits (since 1-9 are all valid hours). The DateTimeHourPart has a Mask property that you could change to "\d{2}", but you'd have to explicitly change it (i.e. it can't be changed using an implicit Style). You could probably do this via an attached behavior, which uses an inherited attached property that looks for DateTimeHourPart/DateTimeMinutePart types.
The problem is the user would still be able to enter a single digit, as the parts just use the MaskedTextBox to ensure only valid digits are entered and doesn't verify the "length" of the text.