What a night I suffered! At 4 p.m., I got a shiny new HP laptop—my first non-Mac in probably a decade—and by 6:20, I was in hysterics, with the Beloved desperately trying to calm me down as I struggled to locate my Dropbox backup on a drive the new computer recognized, but would not display. Here is a recap of my horrific night:

5:40 p.m. We get home, and I plug this puppy in. It takes over 30 minutes to boot up and install ‘app updates.’ Halfway through, the computer starts talking. I’m not sure why.

6:20 p.m. I plug in my backup drive. Nothing happens. I go deep into the setting and try to locate it. I see it listed there, but there is no option to open it or browse it or perform any functions. My entire Calibre library is on this drive, as well as my iTunes library, all my work files and numerous other vital things. With rising hysteria, I interrupt the Beloved, who is on a phone call, to come and help me.

6:30 p.m. He says the drive is not showing up. Maybe it needs a driver. Maybe it is Mac-formatted and so won’t work. I decide to transfer everything onto my ten-year-old MacBook, which the Beloved is now using to browse eBay and play podcasts. I am told the file transfer will take three hours.

6:40 p.m. I decide to go in batches. If I can at least get my eBook library up and running, I’ll keep okay. My Calibre library will fit on a flash drive, so I plug one in and try to transfer it over. The ancient Macbook says it can complete this task in about 45 minutes. Sigh.

6:45 p.m. Meanwhile, I decide to install Evernote. There is a button for that on the desktop. I click on it, and it tells me to please wait while it installs. Um, it didn’t do that during the 30-minute app update? Okay, fine. Install it.

7:00 p.m. Evernote is installed. Huzzah. I launch it, log in, and immediately see my files start zipping in. I am delighted that something is at last working correctly.

7:05 p.m. I get a pop-up that a new Evernote version is available for me to install. Oh. So, it didn’t do that when I installed it? Or during that very long app updating it did when I turned the darned thing on? Huh.

7:06 p.m. The Beloved hears me ranting. For the first time this evening, he offers to return the computer and get me another Mac.

7:20 p.m. My flash drive is ready. I plug it and start transferring it over. I figure that if I can get these smaller files loaded myself, I can save the over-the-cloud Dropbox downloading for the behemoth of my iTunes library.

7:45 p.m. The new computer is at about 60% transferring from my 16 gb flash drive. I get a warning that it is stuck on a few ‘items’ whose file names are too long to be in the directory where I’m trying to put them.

7:50 p.m. Hysterical tears. I just want my books, and thought of going in and manually renaming over 1000 of them gives me hives. The Beloved again offers to go out and buy me a Mac, using wedding money. I refuse. That money is for both of us, and this computer was a bargain. I’ll make it work.

9:00 p.m. I have transferred over as much of my Dropbox library as I can. I am exhausted. I install Calibre, run it, point it to my library. Everything seems to be working so far…

8:00 a.m. I check on things before I leave for work. Dropbox is reporting that it will need 47 more hours to finish downloading my stuff. Sigh.

8:30 a.m. I get to work, check my email and find a note from Dropbox asking me if I want to ‘restore’ the 27,533 files I apparently ‘deleted’ last night. Um, excuse me?

It’s going to me a long week! I will just add as a final note here that my first Windows computer ran Windows 95. So they’ve had 20 years to get the upgrade process right. It should not still be such a trial.

Want to share your own horror stories? At least you know you have company—me!

Image credit: Here.


  1. In my experience when syncing dropbox to new laptop, you must keep your old laptop running together with your new one. Then, dropbox will search and sync between those two laptops within your network, not needing to download it from cloud.
    Or, easier yet, copy your dropbox folder to external drive, then copy it to new laptop. Then you sync your new laptop with dropbox cloud.

    P.s: do not delete dropbox in your old mac without disconnecting the account first. If you do, you will also delete files in cloud as it sync.

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