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The Calendar

PLA 2763Activity 9

Why it Matters

A lawsuit’s deadlines rarely arrive as dates. They arrive as periods, such as twenty days after service or ninety days before docket sounding, and Florida’s courts and the federal courts count those days by different rules. Courts sometimes forgive a missed deadline, when an assistant entered the wrong date or a working office system broke down, but not a firm that never had a real system. Even an excusable mistake cannot reopen the time to appeal, or save a claim filed after the statute of limitations ran. You will turn one case’s periods into dates, race an AI to the same list, and build the two calendars that keep them.

Current Context

In July 2026, in Lupo v. Tractor Supply Co., No. 6:25-cv-02170 (opens in a new tab), a federal magistrate judge in Orlando refused to reconsider an order compelling a company to answer discovery. The earlier order had treated the motion as unopposed and waived the company’s objections other than privilege; the new one let the company produce documents on a rolling schedule. Its lawyers had missed the response deadline because their docketing system applied the 14 days that Local Rule 3.01(d) (opens in a new tab) allows, while the judge’s standing order on discovery motions allowed 5. The court said an inadvertent failure to meet a court deadline is not the manifest injustice that reconsideration requires, and it cited four earlier cases in the district with the same miscount. A docketing program applies the rule it was given, and a judge’s order can change that rule for a single case.

Key Concepts

Computing Time Under Rule 2.514

Florida’s rule for counting any period set by a court rule, a court order, or a statute that does not give its own method. For seven days or more, the count starts on the next day that is not a weekend or legal holiday, runs through every day after that, and rolls a weekend or holiday last day forward. A legal holiday includes any day the clerk’s office observes, and the last day for electronic filing ends at 11:59:59 p.m., eastern time.

Counting Backward

A deadline set before an event, such as expert disclosures 90 days before docket sounding, is counted backward from that event. Under Rule 2.514(a)(5) and Federal Rule 6(a)(5), the next day is then the day before, so a last day on a weekend or holiday moves earlier. Moving it later, as you would for a period counted after an event, puts the deadline past the date the order allows.

Federal Rule 6

Federal Rule of Civil Procedure 6 excludes the day of the event that starts a period and counts every day after it, even when the first day is a Saturday. A weekend or holiday last day rolls forward, and its legal holidays are the federal ones, such as Juneteenth and Columbus Day, plus days the state declares for periods counted forward. It adds three days for service by mail but none for electronic service; Florida adds five days only when a paper is served by mail alone.

Removal

A defendant may move a state case to federal court when the federal court could have heard it, such as a suit between citizens of different states for more than $75,000. The notice of removal is due within 30 days after service under 28 U.S.C. § 1446(b)(1), and until it is filed, the state court’s deadlines keep running. Once the case is removed, Federal Rule 81(c)(2) gives a defendant that has not answered until the later of 21 days after service or 7 days after the notice.

Statute of Limitations

Section 95.11(5)(a), Florida Statutes, gives two years to sue for negligence when the claim accrued after March 24, 2023, and a last day on a weekend or holiday runs to the next court day. Rule 1.540(b) relieves a party from a judgment or order, so it cannot save a suit filed too late. A client’s malpractice claim has its own two-year period under section 95.11(5)(b), and when the error came in a lawsuit that went to judgment, it starts when that judgment becomes final.

Case Management Order

The order that sets a civil case’s deadlines under Florida Rule of Civil Procedure 1.200, from adding parties and disclosing experts to filing motions, around a projected or actual trial period. Its deadlines must be strictly enforced unless the court changes them, and the parties may submit an agreed order extending one only if the remaining dates can still be met. The Seventh Judicial Circuit’s Uniform Case Management Order counts most of its deadlines back from docket sounding or the trial period, which a separate order setting trial fixes.

Docket Control

A firm’s system for recording every deadline, reminding the people responsible, and confirming that each was met. A common design keeps two independent calendars, such as calendaring software and a docket list kept by a different person, each with ticklers, or advance reminders, set ahead of every deadline. Comparing the two on a schedule, and both with the court’s docket, turns one person’s typo or one program’s wrong rule into a disagreement someone can see.

Excusable Neglect

A ground for relief from a judgment or order under Florida Rule of Civil Procedure 1.540(b)(1), on a motion filed within a reasonable time and not more than a year after. Courts have found it in clerical or secretarial error, a reasonable misunderstanding, or a system gone awry, but not where a lawyer forgot a deadline, ignored it, or ran a system with no safeguards. Setting aside a default also takes a meritorious defense and prompt action once the default is found, and a lawyer’s excusable mistake does not reopen the time to appeal.

Resources

What to Do

Sorrelwood Freight Lines was served with a lawsuit on a Friday, and on Monday the papers reach Temko Eden, where finding every deadline in the case is your job. You count each one by hand under the rule that governs it, test an AI against your list, and put the dates on two calendars that check each other. What you post is the calendar and the workbook behind it, which also holds your sort of five missed deadlines by whether a court forgave them.

Part 1: Open the File

Temko & Eden, P.A. A three-lawyer firm on Beach Street in Daytona Beach. It still carries the names of its late founders. Dana Whitfield, the managing partner, handles civil litigation and real estate closings. Luis Ortega, a partner, handles family law and probate, and Kim Nguyen, an associate, handles personal injury. Marcy Cole is the legal assistant, Ron Pike is the bookkeeper and office manager, and you are the firm’s paralegal.

An email from Dana Whitfield, Monday, October 26, 2026. We have a new client. Sorrelwood Freight Lines, a Georgia trucking company, was served on Friday through its registered agent, and its claims manager sent me the papers this morning. Celeste Warrender says one of their tractor-trailers changed lanes into her car on U.S. 1 in Ormond Beach two years ago, and she sued close to the wire. First, tell me whether she made it. Second, I haven’t decided whether to take this to federal court in Orlando. If I do, the notice of removal goes in on Thursday, November 12, so work out our deadlines both ways. I want every date by hand, with the rule behind it, before anyone lets a computer near it. Then put them on the calendar, and I mean two calendars.

Download the workbook and read its Start Here and Case File sheets, which hold every date the papers give you. Open the Uniform Case Management Order from Resources and read sections B through L, because several of its deadlines count from dates the court has not set yet. Then find Rule 2.514 on the Florida Bar’s rules page, in the Rules of General Practice and Judicial Administration, and read subdivisions (a) and (b) before you count anything.

Part 2: Count the Deadlines by Hand

Fill in rows 1 through 7 of the Deadline Chart, the deadlines that start running when the papers arrive. For each one, find the rule, order, or statute that sets it, then count with a calendar in front of you and the Holidays sheet beside it. Use Rule 2.514 for a state court deadline and a Florida statute, and Federal Rule 6 for a federal court deadline and a federal statute. Write down the first day you counted and the last day before any adjustment, because the counting rules do their work at a period’s start and at its end. Row 1 needs section 95.11 and the case in Resources on a limitations period that ends on a weekend. Do not use an AI or a deadline calculator in this Part.

A second email from Dana Whitfield, Thursday, January 14, 2027. We answered in state court and stayed there. The judge’s order setting trial came in today: docket sounding is Tuesday, November 2, 2027, and the two-week trial period starts Tuesday, November 16. Add every deadline in the Uniform Case Management Order to the chart and to both calendars.

Docket sounding is the court’s calendar call before a trial period, when the judge confirms which cases are ready. Fill in rows 8 through 16 from sections F through J of the order. Each of these counts backward from docket sounding or the trial period, so read Rule 2.514(a)(5) again before you start. Row 13 has no number of days, because the order says only that mediation must be finished before docket sounding, so work out the last day that meets it.

Part 3: Run the Deadline Race

Open a fresh chat, run the Deadline Calculator, and paste sections D and F through J of the Uniform Case Management Order when it asks. Copy the AI’s dates into column D of the Deadline Race sheet, and note the tool and model you used at the top. Column E marks every row where the two of you differ. For each difference, run the Count Auditor in a new chat with the text of the rule that governs the row, the right holiday list, and both dates. Check every day of the week it names against a real calendar. Then decide who was right from the rule’s own words, and write that in column F with the subdivision that settles it. If the race shows that you were the one who was wrong, fix your date in the Deadline Chart and say so in the same column. If the AI matched you on every row, run the Count Auditor on the three rows you found hardest anyway.

Part 4: Build the Two Calendars

Your primary calendar is a calendar made for this case alone, in a free tool such as Google Calendar (Resources). Enter every deadline from rows 2 through 5 and 8 through 16 of the Deadline Chart. The limitations period and the two removal deadlines no longer apply now that the case has stayed in state court. Make each one an all-day entry named for what is due and whose deadline it is, and put the rule or order that sets it in the description. Set reminders 30, 14, and 3 days ahead. If your tool will not remind you 30 days ahead, use its longest setting and add the 30-day tickler as an entry of its own.

Then build the second calendar on the Backup Docket sheet: the same deadlines in date order, typed again from the Deadline Chart rather than copied from your calendar. The tickler columns fill themselves. Compare the two calendars line by line, mark each row, and record the date you compared them. Last, export the calendar as an .ics file, which Google Calendar does only from a computer. If your tool cannot export, take a screenshot of each month that holds a deadline.

Part 5: Sort What the Courts Forgive

A note from Dana Whitfield. Before you set up how we calendar, I want to know where the courts draw the line. These five come from Florida appellate cases. Tell me which ones a court forgave, and then give me the procedure that keeps us out of the other column.

Read the five scenarios on the Forgiven or Not sheet and the cases in Resources they come from. For each one, choose Forgiven or Not forgiven, name the case that decides it, and say in a sentence or two which facts made the difference. Run the Motion Hearing prompt on one scenario you marked Forgiven and one you marked Not forgiven, and notice which of the judge’s questions the scenario could not answer. Then write section B, the firm’s calendaring procedure, in 150 to 250 words to Dana. Run the Procedure Stress-Tester on your draft and revise it wherever the prompt finds a gap your procedure does not close.

Part 6: Post Your Deliverables

Create one new discussion thread. Attach the calendar, as an .ics file or screenshots, and the workbook with every sheet filled in. Add three to four sentences naming the row where your count and the AI’s differed most, and the words in the rule that settled it.

Include one AI chat link with a 1–2 sentence explanation of what the conversation shows and why you chose to share it.

Suggested AI Prompts

Use these prompts as a starting point, then adjust them to fit your goal. Strong prompting develops through trial, revision, and testing. It’s a foundational skill that grows into more advanced AI work such as context engineering and agent-based workflows.

Deadline Calculator

Act as the docketing clerk at a Florida law firm. Compute every deadline listed below for a negligence case in the Circuit Court for Volusia County, Florida, in the Seventh Judicial Circuit, and for its alternative in the U.S. District Court for the Middle District of Florida. The facts: the plaintiff was hurt in a crash on Thursday, October 3, 2024, and filed her complaint on Monday, October 5, 2026. The defendant, a Georgia corporation, was served on Friday, October 23, 2026, with the summons, the complaint, the plaintiff’s initial disclosures, and requests for admission. If it removes the case, it will file the notice of removal on Thursday, November 12, 2026. Later, the court set docket sounding for Tuesday, November 2, 2027, and a trial period beginning Tuesday, November 16, 2027. The deadlines: (1) whether the complaint was filed within the statute of limitations; (2) the defendant’s answer in state court; (3) its response to the requests for admission; (4) its initial disclosures; (5) the last day to add parties; (6) the last day to file a notice of removal; (7) its answer if the case is removed; and (8) through (16) the deadlines in the court’s Uniform Case Management Order for expert disclosures by each side, fact witnesses, written discovery requests, completion of discovery, mediation, dispositive motions, expert witness motions, and other pretrial motions. I will paste the order’s sections D and F through J after this message. Then give me a table with, for each deadline, the rule or order, the number of days, the first day you counted, and the deadline. Wait for the order’s text before you answer.

A table that shows the first day counted on every row puts the model’s work where you can check it, row by row. A model counting days has no calendar in front of it unless it runs code, so treat each of its dates as a claim you have to verify.

Count Auditor

I am a paralegal checking one deadline in a Florida lawsuit. I will paste the text of the rule that governs it (Rule 2.514(a) of the Florida Rules of General Practice and Judicial Administration, or Federal Rule of Civil Procedure 6(a)), the court’s list of holidays, the event that starts the period and its date, and two different answers for the deadline. Count the period one day at a time: list each date with its number in the count and its day of the week, and mark any Saturday, Sunday, or listed holiday. Show where the count begins and where it ends, and quote the words of the rule that decide each of those two points. Use only the text I paste. If it does not settle a step, say so instead of guessing. Do not tell me which answer is right until the count is finished.

Decomposition makes the model show every step, and source grounding ties each step to words you can read for yourself. Check each day of the week it gives against a real calendar, because a model can pair a date with the wrong weekday and build the rest of its count on that mistake.

Motion Hearing

Act as a Florida circuit judge hearing a motion under Florida Rule of Civil Procedure 1.540(b)(1) to set aside a default or a dismissal for excusable neglect. I will describe what happened and name the appellate case I think decides it. Ask me one question at a time, the way a judge would at the hearing: who made the mistake, what the firm’s system was and how it failed, what the sworn papers say, how soon the party acted once it knew, and, for a default, what its defense is. Wait for each answer. After five questions, tell me which of my answers would help the motion, which would hurt it, and what else I would need to prove. Do not decide the motion, and do not cite any case I have not named.

Role assignment and Socratic questioning make you supply the facts a judge would ask for, instead of reading a conclusion someone else reached. A question you could not answer points to a fact the scenario left out, and the cases treat such facts as decisive.

Procedure Stress-Tester

Here is the calendaring procedure I wrote for a three-lawyer Florida firm. Read it as a skeptical risk manager and find the ways a deadline could still be missed under it: a lawyer or assistant leaving, a judge’s order that changes a default time, an e-mail address the court serves that no one reads, a holiday list that is out of date, the backup calendar falling behind, and a period counted backward. For each, quote the step in my procedure that would catch it, or say that no step does. Rank the gaps by how likely each is and how much harm it would do. Do not rewrite the procedure for me. Wait for me to paste it.

Red-teaming asks the model to attack your draft rather than approve it, and a model asked for approval tends to give it. The quotation it must give for each safeguard keeps it from crediting your procedure with steps it does not have.

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