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CREATE TABLE #tab(col VARCHAR(100));

INSERT INTO #tab
VALUES ('CVS'),('Walmart'),('Exxon Mobil'), ('Green Mountain Coffee');

SELECT col, 
masked = 
    coalesce(
    -- handle 2 spaces
    STUFF(STUFF(
     STUFF(col, 3, LEN(col)-4, REPLICATE('*',LEN(col)-4)),
    CHARINDEX(' ', col), 1, ' '),
    CHARINDEX(' ', col, CHARINDEX(' ', col)+1), 1, ' '),
    -- handle 1 spaces
    STUFF(
     STUFF(col, 3, LEN(col)-4, REPLICATE('*',LEN(col)-4)),
    CHARINDEX(' ', col), 1, ' '),
    -- normal masking
    STUFF(col, 3, LEN(col)-4, REPLICATE('*',LEN(col)-4)),
    -- too short to mask
    col
    )
FROM #tab;

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edited apr 2 20 anonymous

created dec 3 15 Jeffrey.Yang