Courts have essentially taken three positions when approached with this issue. Some courts take the position that the ADA applies to all commercial sites because the law was meant to protect disabled individuals from having a more difficult time than able-bodied individuals from doing business. That is why the website Scribd was unable to get a case summarily dismissed and ended up settling.
The legal issue for websites is whether website operators are operating “a place of public accommodation.” The statute lists 12 different types of public accommodations including somewhat of a catchall that includes “other sales or rental establishment.” The list, created when the law was passed in 1988, conceivably covers most commercial establishments, but does not expressly include websites.
Because they only read text, screen readers and refreshable Braille displays cannot interpret photographs, charts, color-coded information, or other graphic elements on a webpage. For this reason, a photograph of a mayor on a city’s website is inaccessible to people who use these assistive technologies, and a blind person visiting the website would be unable to tell if the image is a photo, a logo, a map, a chart, artwork, a link to another page, or even a blank page.
On July 26, 2010 (on the anniversary of the Americans with Disabilities Act) President Obama stated that ADA accessibility must also apply to the Internet. With that declaration, the Justice Department was tasked with setting rules for ADA accessibility for the Internet and websites. Since that time, the Justice Department has formulated recommended rules for ADA website accessibility. Those rules will soon be refined and officially released in the near future. Until then, there is a set of guidelines currently in place (http://www.w3.org/WAI/WCAG20/quickref) for websites to become ADA accessible. Even with these guidelines in place, many hospitality businesses have not yet complied with the guidelines. Now is the time to begin the process of making your current website ADA accessible or to consider a new website design that is ADA accessible.
Instead, search online for websites you like and ones that could potentially represent your brand from an image perspective. This is also the time you will begin to draft an outline of what you want your website to accomplish, but we’ll get into that later. For now, figure out why you want a website in the first place to create a starting point for your project.
The large number of people who have disabilities, coupled with the challenges that they face, is one of the reasons that the Americans with Disabilities Act (ADA) was passed in 1990.² As its name suggests, the ADA is designed to protect individuals with disabilities in the United States. The ADA essentially makes it illegal for any government entity or business to provide goods and services to the general public without ensuring that the entities are accessible by people with disabilities. In today’s digitally driven world, many businesses fail to follow web accessibility best practices. In fact, this is why the Supplemental Advanced Notice of Proposed Rulemaking (SANPRM) was created by the U.S. Department of Justice (DOJ). To ensure that they are implementing digital accessibility best practices, organizations are encouraged to use the WCAG 2.1 technical requirements.³

Yes, as of 2018 websites absolutely must be ADA compliant.  Its a new but very scary issue that has flared up over the last year and is set to cause a LOT of turmoil.  The Supreme court issued a judgement that opened up a loophole and opportunity-chasing lawyers are aggressively soliciting handicapped people and convincing them to sue unsuspecting website owners (pretty much every website owner on the planet, as not a single one of us were ADA compliant before now.)
The fact that an ADA compliant website can increase your target audience by millions is just one reason to make your site more accessible. Another benefit is that not only will you get more customers, but those customers will also know how valuable they are to your business. After all, they might have gone to a few other websites that were not ADA compliant, disappointed each time that they couldn’t access the content, until they got to your website.
It’s well-known that the Americans With Disabilities Act (ADA) requires brick-and-mortar businesses be accessible to all patrons. This includes considerations like wheelchair accessibility and Braille or large print for blind and low-vision patrons, among other things. The ADA references “public accommodations,” and outlines 12 categories that essentially covers all types of public-facing businesses. However, the legislation does not address public-facing websites.
Two agencies within the U.S. Department of Labor enforce parts of the ADA. The Office of Federal Contract Compliance Programs (OFCCP) has coordinating authority under the employment-related provisions of the ADA. The Civil Rights Center (CRC) is responsible for enforcing Title II of the ADA as it applies to the labor- and workforce-related practices of state and local governments and other public entities. Visit the Laws & Regulations subtopic for specific information on these provisions.
Do all websites have to be ADA compliant? Does yours? Though the legal definitions are somewhat unclear, it is clear that inaccessibility invites legal action and misgivings from customers. Web accessibility does not have to be complex, and it may not take much to test your site and make it accessible. Take web accessibility step by step and you can avoid stressful lawsuits, and invite all patrons to your website.
Upon discovering issues faced by disabled government employees and the public, revisions to section 508 were made. The issues that were uncovered involved websites, documents, and software programs. As of January 2018, the updated 508 standards require all federal agencies and contractors to create web content accessible to all. The updated standards also include Website 508 compliance.
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!
Web designers often design in such a way that does not allow the user to adjust font size or color. While they may be protecting their brand, they are also inhibiting some users. Many visually impaired need to use high contrast color settings or very large fonts to read a website. Don't design your website in a way that makes it impossible for them to do this. 
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