Pending lawsuit · Orange County, Florida
About the case
A lawsuit over MyCase's Advanced Document Automation (ADA), the document automation feature formerly sold as Woodpecker. The complaint alleges that a known ADA defect was never fixed while 8am kept advertising the product to law firms.
- Case number
- 2026-CC-020794-O
- Court
- County Court, Orange County, Florida
- Complaint dated
- September 17, 2026
- Status
- Pending · discovery
What the complaint alleges
Everything in this section is an allegation in a pending case. 8AM, LLC has not yet answered the complaint, and no court has made any finding.
Plaintiff Jonathan Simon is a legal technology consultant who designs document automation templates for law firms, including firms that use MyCase. MyCase is legal practice management software owned by 8AM, LLC. MyCase acquired the Woodpecker document automation product in 2021, and 8am acquired MyCase in 2022. In January 2024, MyCase moved Woodpecker to "legacy" status and introduced its in-house replacement, Advanced Document Automation.
The ADA defect
The complaint alleges that on January 31, 2024, Mr. Simon reported a defect in ADA: field codes placed inside conditional logic do not populate when a document is generated. Instead, the document "just spits out the field codes." On February 2, 2024, MyCase support wrote that its engineers "were able to reproduce the issue." On April 22, 2024, support wrote that "we do not have a timeline to provide for you." The complaint alleges the defect had still not been fixed when the case was filed.
The advertising
The complaint alleges that 8am continued to market ADA on its website as a complete document automation solution, with no disclaimer about the defect, after telling at least some customers that ADA would no longer be supported and a new product would be developed. Paragraph 20 of the complaint quotes a September 17, 2026 call with 8am's chief executive officer:
Jonathan Simon: "…why are you guys still advertising this on your website if it doesn't work?"
Jeff Hughes: "That's a valid point."
The claims
- Count I, unjust enrichment. The complaint alleges that Mr. Simon spent about 150 hours testing, documenting and debugging Woodpecker and ADA for 8am's benefit without pay, and seeks $15,000.
- Count II, deceptive and unfair trade practices under Florida's Deceptive and Unfair Trade Practices Act (Chapter 501, Florida Statutes), based on the continued marketing of ADA without disclosing the defect.
The plaintiff demands a jury trial.
MyCase's July 2026 email about replacing ADA
On July 21, 2026, MyCase's Manager of Customer Support wrote to a law firm that uses ADA. The email says MyCase decided not to fix ADA's problems one by one and is instead building a product to replace it:
"After reviewing the ADA experience holistically, they've confirmed that rather than patching issues one at a time, they're building a new document automation experience intended to replace ADA and resolve the underlying problems you and others have been running into, adding new and improved functionality."
"…while they don't have a firm release date yet, the team is targeting the second half of this year to begin testing the new experience with select firms."
As of October 28, 2026, MyCase's Advanced Document Automation page still advertises ADA and carries no notice that it is being replaced.
This email is not quoted in the complaint. The quoted lines are exact; the rest of the email is not published here.
Timeline
- MyCase acquires Woodpecker, a document automation product.
- 8am (then AffiniPay) acquires MyCase.
- Mr. Simon begins implementing Woodpecker for a law firm that uses MyCase.
- He raises concerns with Woodpecker's then-CEO, who says he will "properly surface" the feedback.
- MyCase moves Woodpecker to "legacy" status and introduces Advanced Document Automation.
- Mr. Simon reports that field codes inside conditional logic do not populate in ADA.
- MyCase support says engineers reproduced the issue.
- MyCase support says there is no timeline for a fix.
- MyCase support tells a customer firm that a new product is being built "intended to replace ADA," with no firm release date.
- Zoom call with 8am CEO Jeff Hughes; the complaint is dated the same day.
- Counsel for 8AM, LLC appears in the case.
- Plaintiff serves his first requests for admissions, interrogatories and requests for production.
Court documents
Defendant's responses are not posted. This page will be updated as the case moves forward.
Questions
What is Simon v. 8AM, LLC about?
Jonathan Simon sued 8AM, LLC, the owner of MyCase, in the County Court of Orange County, Florida (Case No. 2026-CC-020794-O). The complaint alleges that MyCase's Advanced Document Automation has an unfixed defect, that 8am kept advertising it anyway, and that 8am benefited from his unpaid bug reporting and testing. These are allegations; 8am has not yet answered them.
What defect does the complaint describe?
In ADA, field codes placed inside conditional logic in a template allegedly do not populate when a document is generated. The complaint alleges this was reported on January 31, 2024, reproduced by MyCase's engineers, and still unfixed in September 2026.
Is MyCase replacing Advanced Document Automation?
In a July 21, 2026 email to a customer firm, MyCase's Manager of Customer Support wrote that the Product Team is "building a new document automation experience intended to replace ADA," with no firm release date. As of October 28, 2026, MyCase's ADA web page did not mention a replacement.
I use MyCase. Does this affect me?
This site cannot tell you that. If your firm generates documents with ADA templates that place fields inside conditional sections, you may want to check those documents carefully before sending them, and ask MyCase directly about the status of ADA.
Has the court decided anything?
No. As of October 28, 2026 the case is pending in its early stages. Defense counsel appeared on October 20, 2026, and the plaintiff served his first discovery requests on October 27, 2026.
Is this site affiliated with 8am or MyCase?
No. This site is run by the plaintiff. It is not affiliated with, endorsed by, or sponsored by 8AM, LLC, MyCase or AffiniPay.
How can I get in touch?
If you have information relevant to the case, email Suitedaces44@gmail.com.