Does it have a limit? Count of the items - is it 30 or 100? Is Web work the same way like Desktop? There're limits on prompt level, attribute level (?) and web level.
Turn on SQL Trace. Grab the SQL that is generated to populate the prompt. Based on the SQL shown here, you should be able figure out why it is returning a limited amount of elements. If you run the SQL against the database using it's native app, and it brings back the correct amount of elements, then clear your element cache.
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