How is my password manager experiment working so far?

A couple of weeks ago, I wrote that I had started experimenting with a password manager. I thought I’d give an update on how it’s working for me so far.

Here’s what I do:

1. I use my Windows 8 laptop as my main machine at work. Most of the time when I want to save a new password, I add it to ComboPass (my fictional name for a real piece of software) on this machine.
   
   
2. However, I don’t always use my Windows 8 laptop, especially at home. I use my old Windows 7 laptop at home because I have my personal email sync’ed with Thunderbird on it (I am too lazy to copy over the email folders to the new machine) and because I have an extra power cable for it at home, whereas my Windows 8 machine I only have one power cable at the office. I don’t want to carry it home so I just use my Windows 7 machine at home.

On both machines, I have ComboPass set up and sync’ing the password file via SkyDrive Pro. This is the only corporate-approved mechanism of storing the database (I can’t use a personal one like SkyDrive regular since it is not encrypted, and SkyDrive Pro is).

As I was getting used to it, I thought to myself “Hey, this is pretty good! Maybe I should have done this years ago.” But as I started using it more, I got the feeling that I am doing something wrong.

This password combination with sync’ing seems more difficult than it needs to be. If I only ever add passwords while using my Windows 8 machine, it seems to work okay. And if I just read passwords from my Windows 7 machine, it works okay.

But heaven help me if I ever want to add passwords using my Windows 7 machine! Why? Because I keep getting upload failures:

When I try to resolve other files that similarly failed to upload:

The password file keeps failing to sync and upload. I think it’s a race condition – the file is being actively used on my Windows 8 machine and my Windows 7 machine, and SkyDrive Pro cannot upload and overwrite it if it is currently in use.

This file keeps failing to upload and I have to manually sync it (sometimes by transferring it with USB sticks). This happens on both machines. Isn’t this supposed to do it automatically? Why do my downloads keep failing? Why do I have to hack around it?

What’s more, I recently rebooted my Windows 8 machine and ComboPass wasn’t running when I restarted (it couldn’t find the file saved on SkyDrive Pro which wasn’t sync’ing). It took me a while (15 seconds) to figure out where I had stored it so I could get it up and running again – manually. I know this is a simple task, and it only took me a minute to figure it out. But isn’t it supposed to start running automatically when I reboot? The way it does on my Windows 7 machine? How am I supposed to recommend this to average people?