Navigate to %localappdata%\Red Gate\SQL Prompt 11\SqlHistoryIndex and rename the SQLHistory.db file to something like "SQLHistory_OLD".
Then re-open SSMS and a new SQLHistory.db file should be created in that folder.
If it still fails, please raise a support ticket with a copy of the SQL Prompt log files. To find the log files for the current session, open the SQL Prompt menu, click Help and then click Zip Log Files.
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