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Previous research has revealed that newcomer women are disproportionately affected by gender-biased barriers in open source software (OSS) projects. However, this research has focused mainly on social/cultural factors, neglecting the software tools and infrastructure. To shed light on how OSS tools and infrastructure might factor into OSS barriers to entry, we conducted two studies: (1) a field study with five teams of software professionals, who worked through five use cases to analyze the tools and infrastructure used in their OSS projects; and (2) a diary study with 22 newcomers (9 women and 13 men) to investigate whether the barriers matched the ones identified by the software professionals. The field study produced a bleak result: software professionals found gender biases in 73% of all the newcomer barriers they identified. Further, the diary study confirmed these results: Women newcomers encountered gender biases in 63% of barriers they faced. Fortunately, many the kinds of barriers and biases revealed in these studies could potentially be ameliorated through changes to the OSS software environments and tool.