Women are a powerful economic force in the world’s wine market, with marketing of wines made by women to female consumers increasingly important. It is widely assumed that women winemakers in California have shattered the glass ceiling, but few studies have addressed their progress in what remains a male-dominated field. This paper reports on three separate studies assessing their progress. Study 1 assessed the perception that women winemakers have shattered the glass ceiling. Results showed that only 9.8% of California wineries have a woman as the lead winemaker, illuminating a discrepancy between perception and fact. Study 2 investigated whether winery acclaim was associated with this discrepancy. Coding of winery data in Opus Vino (2010) provided support for the hypothesis of proportionally greater acclaim for wineries having women as their lead winemakers. Study 3 tested the hypothesis that the recent increased recognition and visibility received by lead women winemakers is opening doors for other well-qualified women. Using the wineries included in Wine Spectator’s California Wine (1999) for a case study, the same set of major wineries was investigated at two times—1999 and 2014. Two approaches were taken to assessing progress: comparing the percentage of wineries with lead women winemakers at both times, and comparing the percentage, taking into account position availability and pattern of gender hiring into available positions. Results showed some increase, 10% in 1999 to 14.7% in 2014 overall, and 20.5% when considering only available positions. Progress appears steady but slow.