The gray area is a matter of scale and purpose. If you have a small business which serves as specific market it's a good idea to make the site as user and disability friendly as possible. If, however, your market serves segments with a likeliness to have various handicaps or disabilities you should address that with an ADA Compliance review of the site. Also consider the scale and purpose of an organization. Publicly traded large businesses need to concern themselves more than a single location family owned retailer and if someone sues your flower shop because the text was too small or didn't have "image alt tags" causing them distress... That's pretty frivolous and would likely not stand. 

Currently, the law is a little bit murky when it comes to ADA compliance on a website. Courts have been interpreting ADA in various ways when it comes to website compliance. Some courts have stated that any US business must have an ADA-compliant website. Some courts have said that the website must have a “nexus” to a physical location which must be ADA compliant before their website must also be compliant. This is why Facebook was able to dismiss a 2011 ADA case in California, but Home Depot was no...
I have previous experience with a company that sold a platform to help alleviate ADA compliance issues on websites. From my understanding litigation is being brought to a few industries with it beginning to trickle down into others. Government agencies, education, banking, and law firms were some of the early initiators that were paying more attention to ADA before any lawsuits approached their door.
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Being one-third of the way into 2019, we opted to follow up on the 2018 discussion we had regarding ADA Website Compliance. Per last year, making sure your website is ADA compliant is significant in offering an equal opportunity for everyone to experience the products and/or services your business offers. An ADA compliant website also help prevent lawsuits and potential government action.
The text in the ADA did not originally mention websites since this technology was not widely used in 1990. But now that most businesses have a website, they need to make sure it’s accessible to everyone. Since we’re past the ruling date, all updated pages on your website are required to be at least grade A complaint, with grade AAA being the highest.
If you return your availability by room type your our online booking engine must also display and hold accessible rooms only for people with disabilities until all other rooms have been booked. (Rule becomes effective March 15, 2012.)  If you return your availability by individual units you do NOT have to hold ADA rooms back until all other units have been reserved.  However, all other ADA regulations do apply (ADA room descriptions, using a booking engine that is ADA compliant, and making your website ADA accessible).
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The U.S. Department of Transportation enforces regulations governing transit, which includes ensuring that recipients of federal aid and state and local entities responsible for roadways and pedestrian facilities do not discriminate on the basis of disability in highway transportation programs or activities. The department also issues guidance to transit agencies on how to comply with the ADA to ensure that public transit vehicles and facilities are accessible.
The question of ADA’s exact wording comes down to two issues: 1) whether the ADA applies to a website at all, and 2) if ADA applies only to websites that have a physical connection to goods and services available at a physical store or location, or if it applies to all websites even if they don’t have physical spaces. Courts are split on these issues but one thing is for certain: the tide is moving toward ADA compliance for websites, and the lack of specific legal wording prohibiting web discrimination has not stopped businesses from being sued.
That carousel or image slider on your site looks beautiful. That stunning video on autoplay may have cost thousands to produce. Users with cognitive limitations, however, may not comprehend your information quickly enough before the view changes or your video ends. Other users may want to start over, or go back and review something they saw or heard.
Legal precedent is changing, and ADA compliance related lawsuits are becoming more successful, and the courts are seeing more of them as a result. Title III of the Americans with Disabilities Act pertains to private sector businesses. Lately, those protections are more frequently expanding into digital territory as web and mobile applications become more necessary in our day-to-day lives.

Now you know that some types of content and format on webpages can pose barriers for people with disabilities. The next steps are to develop an action plan to fix web content that is currently inaccessible and implement procedures to ensure that all new and modified web content is accessible. The website accessibility checklist included in this section helps you assess what needs to be done.
If you do get sued, if you immediately remediate your website, you may be able to get the lawsuit dismissed on mootness (there’s no longer anything in dispute, i.e. plaintiffs are arguing your website is inaccessible but you’ve already made it accessible). This definitely does not mean you should wait to fix your website but it does mean you may have an out.
That’s good news if you are one of the many Americans who have a visual, hearing, or mobility disability that makes it difficult to access some information on the web. If you are a business owner who hasn’t made provisions to ensure that your website and other online assets are ADA compliant, you could be looking at a host of legal and financial penalties.
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 ADA is the Americans with Disabilities Act, passed almost 30 years ago in 1990. This act was originally put in motion pertaining solely to physical location. It requires establishments to provide people with disabilities easy access to various levels throughout the business. This act was set to achieve an equal experience to all people, handicapped or not.
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