It will annotate all the elements of a web page and point out any issues. The other tool is WAVE, which will provide you with a detailed accessibility analysis of the current page. Each tool will have its own button displayed on the bottom of your site to logged in users (you can choose which user roles will see the buttons). Just click the button of your choice to start analyzing.
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!
Level AA is a little more significant, and makes sites accessible to people with a wider range of disabilities, including the most common barriers to use. It won't impact the look and feel of the site as much as Level AAA compliance, though it does include guidance on color contrast and error identification. Most businesses should be aiming for Level AA conformity, and it appears to reflect the level of accessibility the DOJ expects. 
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.
If the user selects this button, the page is read aloud while text is highlighted. This is powered by ReadSpeaker, which I think is a really cool product. It provides improved accessibility to a vast audience of people who might not otherwise have their own assistive technology, such as people who are not native to the language of the page, or people with dyslexia or other reading challenges.
Video remote interpreting (VRI) is a fee-based service that uses video conferencing technology to access an off-site interpreter to provide real-time sign language or oral interpreting services for conversations between hearing people and people who are deaf or have hearing loss. The new regulations give covered entities the choice of using VRI or on-site interpreters in situations where either would be effective. VRI can be especially useful in rural areas where on-site interpreters may be difficult to obtain. Additionally, there may be some cost advantages in using VRI in certain circumstances. However, VRI will not be effective in all circumstances. For example, it will not be effective if the person who needs the interpreter has difficulty seeing the screen (either because of vision loss or because he or she cannot be properly positioned to see the screen, because of an injury or other condition). In these circumstances, an on-site interpreter may be required.
The U.S. Department of Health and Human Services (HHS) also enforces Title II of the ADA relating to access to programs, services and activities receiving HHS federal financial assistance. This includes ensuring that people who are deaf or hard-of-hearing have access to sign language interpreters and other auxiliary aids in hospitals and clinics when needed for effective communication.

...the full and equal enjoyment of the goods, services, facilities, or accommodations of any place of "public accommodation" by any person who owns, leases, or operates a place of public accommodation. Public accommodations include most places of lodging (such as inns and hotels), recreation, transportation, education, and dining, along with stores, care providers, and places of public displays.
Federal law isn't the only consideration for businesses. Additionally, each state interprets the law differently. Consider the case against Netflix in 2012. Lawsuits were brought in federal court in Massachusetts and California. Netflix was accused of violating the ADA by not offering "closed captioning" options for its Internet streamed movies. Illustrating the complexity of this issue, the courts reached completely opposite decisions. Massachusetts held that Netflix must comply with the ADA, while the California court found that Netflix did not fall under the ADA's definition of "public accommodation."
It’s most outward feature is a font size and color contract toolbar that helps users more easily read your content. But it also does a lot of behind-the-scenes work like adding skip-to-content links, implementing an outline to the link :focus state for better keyboard navigation, utilizing longdesc for images and a whole lot more. Each feature can be turned on or off through a settings page.

When you insert an image into a post or page, consider providing a rich description for the caption that will improve the reading experience for everyone, but especially folks who can’t see the image. Be creative. Instead of “My son on his swing,” try “My son is playing on his favorite swing. His face is filled with pure joy on a beautiful Spring day. Perfection.” The goal here is to convey the feeling of the image.
Error prevention on important forms (3.3.4): For pages that create legal commitments or financial transactions or any other important data submissions, one of the following is true: 1) submissions are reversible, 2) the user has an opportunity to correct errors, and 3) confirmation is available that allows an opportunity to review and correct before submission.
A critical and often overlooked component of ensuring success is comprehensive and ongoing staff training. Covered entities may have established good policies, but if front line staff are not aware of them or do not know how to implement them, problems can arise. Covered entities should teach staff about the ADA's requirements for communicating effectively with people who have communication disabilities. Many local disability organizations, including Centers for Independent Living, conduct ADA trainings in their communities. The Department’s ADA Information Line can provide local contact information for these organizations.
In addition, aids and services include a wide variety of technologies including 1) assistive listening systems and devices; 2) open captioning, closed captioning, real-time captioning, and closed caption decoders and devices; 3) telephone handset amplifiers, hearing-aid compatible telephones, text telephones (TTYs) , videophones, captioned telephones, and other voice, text, and video-based telecommunications products; 4) videotext displays; 5) screen reader software, magnification software, and optical readers; 6) video description and secondary auditory programming (SAP) devices that pick up video-described audio feeds for television programs; 7) accessibility features in electronic documents and other electronic and information technology that is accessible (either independently or through assistive technology such as screen readers) .
Video remote interpreting (VRI) is a fee-based service that uses video conferencing technology to access an off-site interpreter to provide real-time sign language or oral interpreting services for conversations between hearing people and people who are deaf or have hearing loss. The new regulations give covered entities the choice of using VRI or on-site interpreters in situations where either would be effective. VRI can be especially useful in rural areas where on-site interpreters may be difficult to obtain. Additionally, there may be some cost advantages in using VRI in certain circumstances. However, VRI will not be effective in all circumstances. For example, it will not be effective if the person who needs the interpreter has difficulty seeing the screen (either because of vision loss or because he or she cannot be properly positioned to see the screen, because of an injury or other condition). In these circumstances, an on-site interpreter may be required.

State and local governments: in determining whether a particular aid or service would result in undue financial and administrative burdens, a title II entity should take into consideration the cost of the particular aid or service in light of all resources available to fund the program, service, or activity and the effect on other expenses or operations. The decision that a particular aid or service would result in an undue burden must be made by a high level official, no lower than a Department head, and must include a written statement of the reasons for reaching that conclusion.
The ADA guidelines provide the foundation that organizations need to achieve digital accessibility best approaches, however they are not exhaustive. They do not provide direction for all of the accessibility challenges that people with disabilities face. They also fail to provide detailed technical instructions. With these limitations in mind, there is a ray of hope.

You probably won't have to check your site with all of the available evaluation tools out there, but it is a good idea to do so for the most common web browsers. Just as accessibility software makes it easier for people with disabilities to navigate the Internet, these tools make it easier for developers to ensure accessibility from the start. When you think you've mastered it, go back through the Section 508 compliance checklist to ensure you've met every goal.
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