If Chrome and Safari are both based on WebKit, does that mean I don’t have to test both browsers?
… or are there certain situations where I should explicitly test both Chrome and Safari?
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Everything else beside the basic HTML rendering engine is still different. If only basic HTML/CSS compatibility is important, I guess it’s fine to test one browser.
However, the JavaScript engines of Chrome and Safari are completely different, vector graphics are rendered by different engines, HTML5/video tag stuff is implemented completely different, etc. The list goes on.
Overall I’d recommend to test with both browsers.