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SQL Prompt does not examine UDT information. sysname, although it is just a string, is actually a UDT. Therefore, SQL Prompt is unable to find its precise type and so is unable to insert an appropriate default value.
It may be possible in a future version of Prompt to extract UDT information and insert appropriate default values. I'll log this is a suggestion for a future version. Thanks for your input!
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eg:
(recache DB)
Type INSERT INTO DummyT<prompted to complete - press completion key>
results in:
Running SQLPrompt 3.6.0.109