Securing a laptop when the IT staff can't

A tech tale of a personal laptop, VPN installation, and keeping company data secure

Although I am not a tech support person, I have spent most of my working life around computers. Also, I have done enough boneheaded things on computers to have figured out that the keys to my professional happiness are to A) never irritate the IT department, for their methods of revenge are brutal and ingenious, and B) figure out how to troubleshoot and solve my own problems. This troubleshooting comes at a price -- namely, I'm now the tech support for my entire family.

Recently, my mother tangled with a home renovation project and ended up with several broken bones. Because she is in a cast to the knee and a cast to the elbow, she is more or less confined to a chair at home, on account of the doctor's orders to avoid putting pressure on either her arm or leg.

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My mother is the payroll supervisor for a multistate, 300-person firm, and the temp they brought in was making a hash of the books. Since she was getting bored on disability leave, Mom called her boss and offered to work remotely. The boss was enthused by this idea; his boss, however, said he didn't want to send over a spare machine, because what if someone in the office needed it? My mother volunteered her personal laptop. So Mom's workplace decided she could install some VPN software and work from the comfort of her sickbed.

Mom told her firm's IT staff that she works on an Apple iBook G4, passed along her operating system, and waited for someone to send her whatever CDs she'd need to install the software. Then she asked me to install the software.

Unfortunately, the tech had sent along .exe files. I quickly read the Readme file and confirmed that the IT department had sent along Windows-only software. I got on the phone with the IT department and explained the problem, asking if they had the Mac OS X version of the VPN software.

"It's too big to burn on a CD, so let me e-mail it to you," said the IT tech. That was my first clue that perhaps the IT department wasn't all that familiar with Mac-only software.

When attempting to e-mail a .dmg file failed (unsurprisingly), I called the IT department again to ask if I could just bring the laptop in and have the department install the software.

"I don't know," said the tech. "It's not secure to have you or an unsecured laptop on the physical premises."

Bear in mind that the point of bringing the laptop onto the premises was to secure it. Bear in mind also that the whole purpose of this exercise was to allow my mother to download and manipulate files that contained all sorts of confidential company and personnel information. She'd have this information saved to her personal laptop's hard drive -- which seems none-too-secure itself. But I'm not an IT professional, so what do I know?

Eventually, I was approved to come in to headquarters with the laptop and escorted to the IT department. There, the IT tech took one look at the iBook G4 and said, "I haven't worked with Apple since my school days. I had an Apple IIe. They've changed."

To make a long story short, I ended up installing the software myself and setting up the VPN configurations. The IT tech was ecstatic over learning about a new platform. And I did not walk out with any valuable company secrets, so all the company has to worry about is the fact that all their payroll data is on an employee's laptop offsite. How fortunate that neither the laptop -- nor my mother -- are going to be walking out the door any time soon.