Apparently until recently, the Linux kernal value that measures “uptime” was a 32 bit number. Uptime is measured in centiseconds (.01) and thus after 497 days, 2 hours, 27 minutes and 53 seconds, the counter wraps around to zero. Doing a Google search on “Linux uptime 497“ produced a number of folks who encountered the issue and discussions about it.
Now, I doubt that this is a big deal in the grand scheme of things. I honestly don't know if Windows has similar limitations. Obviously Linux can stay up longer than 497 days, it just won't be reported as doing so.
What struck me as odd about this particular problem was the response of the user community. Many of the replies to folks bringing up the issue go along the lines of “if you go 497 days without rebooting, you're a security risk because you haven't applied kernel patches.” Example here and here.
I'm certain that if Windows had such an issue, it would be proudly proclaimed by the Linux user community as evidence of shoddy programming on the part of Microsoft. They would be right. Of course, the Windows user community couldn't care less about shoddy programming in the Linux universe so, other than right here, you're unlikely to hear about such problems. I suspect that Ziff-Davis (motto: “Pravda for the Linux State“) won't be running any commentary about the “uptime rollover bug.“
I stumbled apon all this when researching which OS was being used by major web sites for it's servers. Netcraft offers a page showing the average longest uptimes of the web sites it tracks. The Top 50 sites is dominated with BSD/OS, which accounts for all but 7 of the entries including the top 5 sites. #1 is 1,786 days by Netcraft's count.
#6 is 1,618 days and is running FreeBSD. No one in the BSD community thinks such a high number is out of place or indicates a insecure system. In fact, the version of Apache running on the #5 site is 1.3.26, which was released in June 2002. So obviously the site is getting secuirty updates, it just doesn't need reboots to make them happen...
...and that, my friends, is exactly the way it should be.