Hey Casey, this is one of the areas where things get a little weird because the W3 doesn’t actually have any say over the ADA guidelines, it is more than the ADA guidelines adopted the WCAG 2.0 guidelines as just that, a guideline to help. As far as I know, the tool you’ve linked to hasn’t been used in any judgements I’m aware of. Usually when it comes down to making a decision on if something is/isn’t compliant they have people use the actual PAWS tools and show what elements do/don’t work as intended or are otherwise inaccessible. Hope this helps!
ADA compliance isn’t a set-it-and-forget-it thing. Compliance standards must be followed and will evolve just as your website does. There are guidelines all website contributors must know to stay within ADA guidelines. It is generally not burdensome but it does require some web managers to change their workflows. For example, loading images up to your ecommerce site will always need some of that alternative text (alt tags) mentioned above.

In an August 2016 case involving the University of California Berkeley, the DOJ ruled that the public university was in violation of ADA Title II (similar to Title III but it instead applies to government organizations) because their YouTube channel’s videos didn’t include captions for hearing impaired visitors. The DOJ found this to violate the ADA as deaf users did not have equal access to the online content.


Once you have been hired and started work, your employer cannot require that you take a medical examination or ask questions about your disability unless they are related to your job and necessary for the conduct of your employer's business. Your employer may conduct voluntary medical examinations that are part of an employee health program, and may provide medical information required by State workers' compensation laws to the agencies that administer such laws.
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