By Aidan Malley

Published: 12:00 AM EST

Experts have put Apple's security to the test -- just as Microsoft prepares to test the iPod's longevity, and the European Union readies an antitrust challenge to iTunes.

Report: Apple's security good, but wanting

A number of security firms have leveled criticism at Apple for some of its security practices with Mac OS X, saying that the company's hubris could invite trouble -- though adding that criticism wasn't entirely deserved.

Apple has repeatedly taunted Microsoft with the self-proclaimed superiority of its security through its advertising, said McAfee researcher Craig Schmugar. This may have helped the company's popularity but may have equally drawn more unwanted scrutiny.

"Recently, the Mac ads may be playing a role in making people go looking for flaws. They seem to be bragging a little more than they should," he said.

The claims could potentially cause trouble given Apple's bad habits, other critics added. While Apple can take comfort in a smaller marketshare, the company's responses to security holes have typically been sluggish at best, based on a Symantec security report.

Microsoft has typically taken much less time to patch issues and rolls out fixes in an average of 21 days -- far outpacing Apple's ever-slowing pace, which now averages 66 days between fixes. Just six months ago the firm patched Mac OS X at a still slower rate of 37 days. The infamous Month of Apple Bugs is said to have jolted Apple out of a much-needed complacency.

Nevertheless, Apple isn't yet in danger of a collapse. SANS Institute chief researcher Johannes Ullrich noted that Mac OS X was, overall, a better prospect for those concerned about malware attempts.

"It's still safer, but not as safe as Apple pretends it is," Ullrich commented. "Some features, like the firewall, aren't all that great. But, yes, it's still pretty safe."

Microsoft preps second-wave Zune attack

Meanwhile, Microsoft is still confident that its Zune will claw away some of the iPod's marketshare by striking at some of the player's best-known selling points.

"We have a second wave of marketing and advertising coming out next month," said Zune's marketing head Jason Reindorp, who elaborated that his company would point out the Zune's advantages over the iPod. The Microsoft-made device is recognized mainly for its selective Wi-Fi music sharing and its customized interface.

More importantly, Reindorp added, are new products. The campaign will start modestly with new colors for the present-day 30GB model but should grow as new features are added. Flash devices were a strong possibility given their popularity.

"We are indeed considering if they might complement the Zune device family," he noted.

Apple caught up in new EU probe

Apple's troubles were compounded on Monday when the European Commission officially accused Apple and the four major music labels of anti-competitive practices in the deals that form the backbone of today's iTunes Store.

At the heart of the complaint was the nationalized approach to the online music shops, which are restricted only to buyers who hold accounts in given countries. Shoppers are often forced to buy only from their home store, preventing them from earning the best rate. British shoppers are particularly hurt by this, the EC said, as the 79p song downloads were the most expensive across the whole region.

The iTunes operator hinted that it had been pressured into using only localized stores and denied that it had stepped outside legal bounds when it accepted the terms that led to today's fragmented iTunes marketplace.

"Apple has always wanted to operate a single, pan-European iTunes store, accessible by anyone from any member state," Apple's spokesman told the press. "But we were advised by the music labels and publishers that there were certain legal limits to the rights they could grant us. We do not believe the company did anything to violate EU law, and we will continue to work with the EU to resolve this matter."

The accusation landed just as Apple was poised to ease earlier European concerns by removing DRM from EMI's music library on a worldwide basis.