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The Chronicle of Higher Education (subscription required) on legal questions raised by new software designed to monitor students’ activity on popular social networking websites like Facebook.com and Myspace.com.

The program, called YouDiligence, was developed by MVP Sports Media Training and is targeted towards college athletic departments concerned about the online activities of their student-athletes. MVP’s describe YouDiligence as “the first product designed to help college athletic departments monitor the potentially damaging Web postings by their student-athletes”:

Do you know what your student-athletes are posting online? That is a question that is leaving more and more college athletic directors and sports information directors deeply concerned. With the recent trend of college students using and abusing social websites, their postings have generated controversy on dozens of campuses nationwide, damaging the image of the athletic department, the school and the student-athletes themselves.

This is not a problem confined to revenue sports or Division I schools. EVERY program at EVERY school in EVERY Division needs to be vigilant about what material their student-athletes are posting on these sites. No school or program is immune from the damage that can be caused by careless postings and poor decisions by maturing student-athletes.

Many schools have chosen to have staff members spend part or all of their days manually monitoring these sites. This is not only a waste of their time and abilities, it is not an effective method for monitoring the activity. However, given the vast majority of student-athletes have social websites, it is clear something has to be done. Poor decisions by student-athletes result in negative headlines for universities.

The Chronicle article explains that YouDiligence works by conducting searches of student Facebook and MySpace pages for “up to 500 objectionable words and phrases ranging from profanity to slang used to describe drugs.” If a given phrase is discovered on a student page, a report is automatically generated and e-mailed to the relevant college administrator. From there, as MVP’s promotional materials put it, “[w]hat you decide to do with that information is entirely up to you.”

But as The Chronicle notes, YouDiligence raises serious questions about the constitutionality of proactively monitoring online student speech. Of course, students at public schools enjoy the protection of the First Amendment; therefore, punishment meted out on the basis of speech is typically unconstitutional. However, the constitutionality question is complicated by the fact that many student-athletes accept athletic scholarships, the terms of which typically require an athlete to agree to abstain from “unbecoming conduct” or some similar heightened standard.

Even if increased online scrutiny for student-athletes passes constitutional muster, which is by no means clear,ethical questions about the use of a product like YouDiligence remain: Does the online student speech monitored by YouDiligence really fall under the purview of collegiate athletic departments? What degree of privacy can a student-athlete expect to enjoy? Further, if schools feel comfortable monitoring online speech for athletes, what is to stop them from extending their observations to the general student population? The Chronicle quotes FIREPresident Greg Lukianoff raising this precise concern:

But Greg Lukianoff, president of the Foundation for Individual Rights in Education, said the fact that universities can, and do, exert greater control over their athletes’ behavior does not mean programs like YouDiligence could not be used in the future to monitor online activities among the broader student population.

“I think we’d be naïve to assume that this software is only going to be used to police student-athletes,” Mr. Lukianoff said. Universities, he said, have a “nasty habit” of monitoring speech they find offensive. “And now they have a wonderful tool to police the Internet more efficiently.”

At one point, punishment for online speech was a novel occurrence at our nation’s institutions of higher learning. By now, however, FIREhas seen many, many cases involving students punished for online speech. Indeed, as students T. Hayden Barnes and Justin Park can testify, two of our three Red Alert schools—Johns Hopkins University and Valdosta State University—were deemed the “worst of the worst” when it comes to student rights in large part because of their draconian reactions to online student speech.

Unfortunately, not much has changed since Greg and I wrote about the problems presented by online student speech in a cover story for The Boston Phoenix last year. In light of the advent of products like YouDiligence, what Greg and I concluded then rings just as true now:

With so many in-jokes and candid moments floating around cyberspace in infinitely reproducible digital formats, privacy is quickly succumbing to a digital onslaught of personal information run wild. How do we as a society deal with living lives more publicly than ever before? Maybe we simply have to become more sophisticated and accept that people behave badly sometimes, just as they always have; the only difference now is that we can see that misbehavior in color on our Web browsers. As the information citizens have about one another approaches the infinite, respecting privacy will increasingly be a duty incumbent upon the viewer…. First Amendment case law provides real and useful wisdom and guidance to universities considering expanding their speech codes into the virtual world: it is a bad idea to police humor, it is a terrible idea to enforce taste, and politeness, while commendable, must not be the law. Attempts to do so result in arbitrary enforcement and abuse.