Specifically, four minutes and twenty-seven seconds.
I've known about this order for a while now—it was issued in a case called Hyperphrase Technologies v. Microsoft Corp. in 2003—but was surprised to note (after somebody sent it to me today) that I apparently haven't posted it here yet. It belongs on the Noteworthy Court Orders page so that's where it's going now.
The brief order concerns a motion to strike (basically an objection to a document, but "motion to strike" sounds more dramatic) that was aimed at a summary judgment motion filed by Microsoft. The motion was due on June 25, 2003, and as in most federal courts, an electronic filing anytime before midnight is considered timely. The magistrate judge describes what happened next:
In a scandalous affront to this court's deadlines, Microsoft did not file its summary judgment motion until 12:04:27 a.m. on June 26, 2003, with some supporting documents trickling in as late as 1:11:15 a.m. I don't know this personally because I was home sleeping, but that's what the court's computer docketing program says, so I'll accept it as true.
(Emphasis added.) Well, that is a clear violation of the court's order, and so the other side's team of lawyers sprang into action:
Microsoft's insouciance so flustered Hyperphrase that nine of its attorneys, namely [names omitted here but listed in full by the court for shaming purposes] promptly filed a motion to strike the summary judgment motion as untimely. Counsel used bolded italics to make their point, a clear sign of grievous iniquity by one's foe. True, this court did enter an order on June 20, 2003 ordering the parties not to flyspeck each other, but how could such an order apply to a motion filed almost five minutes late? Microsoft's temerity was nothing short of a frontal assault on the precept of punctuality so cherished by and vital to this court.
At this point you may have detected a certain amount of sarcasm and so may be able to predict the outcome of this motion, but I'll go ahead and give you the rest anyway:
Wounded though this court may be by Microsoft's four minute and twenty-seven second dereliction of duty, it will transcend the affront and forgive the tardiness. Indeed, to demonstrate the even-handedness of its magnanimity, the court will allow Hyperphrase on some future occasion in this case to e-file a motion four minutes and thirty seconds late, with supporting documents to follow up to seventy-two minutes later.
Having spent more than that amount of time on Hyperphrase's motion, it is now time to move on to the other Gordian problems confronting this court. Plaintiff's motion to strike is denied.
(Emphasis in original.) It is still the case that you should never miss a deadline, because you never know what a particular judge or court may do; but on the other hand, it is also a good rule of thumb to avoid being too petty.
I would give it at least five minutes before you file anything.