The 5 Backup Strategy Mistakes You’ve Already Made

Feeling safe and secure with your backup solution? Not so fast. Fix these mistakes now or you’re at risk of catastrophic data loss.

Although most of us know the importance of a good backup solution to prevent data loss, not all of our backups are reliable. Sure, we set it up at some point.  The problem is that the “set it and forget it” approach often leads to data loss. But planning and testing can help you identify backup problems before it’s too late.

In a nutshell:

Mistake #1: You’ve forgotten your password.
Solution: Record your password and keep it in a safe place.

Mistake #2: Your free trial backup software or service has expired.
Solution: Read terms carefully and purchase the software; update credit card information for automatic renewals.

Mistake #3: You aren’t backing up what matters.
Solution: Don’t trust the default settings; review your backed-up files and make sure your important files are there.

Mistake #4: You don’t realize the limitations of your backup solution.
Solution: Don’t just back up your personal documents; back up installers, serial keys, and everything else that you’ll need to restore your system to working condition.

Mistake #5: You’ve never tested your backup.
Solution: Run a backup drill once or twice a year (sync up with daylight savings) to ensure your backup really works.

1. Passwords and Protected Backups Locked Forever

A backup is another copy of your data, by definition. To keep that data safe, especially when it’s online, you need a password.  Preferably that password is unique, so you’re protected when databases get hacked.  You might even have enabled two-factor authentication (2FA) (I have it set up on mine).

Photo by JD Hancock

When you go to restore your data, though, will you remember that password? If you set it up long ago and didn’t record it, your backup won’t do you much good.  A good example of this problem is Apple’s Time Machine backup.  If your hard drive is encrypted, your Time Machine is probably encrypted.  Apple stores all these passwords in your keychain.  If your hard drive dies, you’ll lose that keychain.  Then when you try to get to your backup data, you’ll need that password you relied on your Mac to remember.  Lots of third-party software works the same way.

Wait!  If it’s an online backup, you must tell them you forgot your password, and they’ll email you the link, right? That will work unless you change your email address since you set it up.  I see this all the time.  That old email address could have been with an employer, school, or ISP.  You might even have been locked out of that address with all the email hacks.  Guess what?  You’re locked out of your backups as well.


Keep your backup password and account information up to date.  Store your password in a safe place, sometimes literally.  I keep mine in a fireproof safe.  If it’s an online backup, log in and make sure your information is current.  While you’re in there, check to see if they offer 2FA and enable it.

2. Your Backup Account Expired

When you set up your backup, everything was working great.  You wrote down your password, so you dodged that gotcha above.  You might have even tested it to make sure it worked—at least the first time.

Fast forward to today, and you didn’t realize that bundled software was a limited trial.  Oops.  That backup stopped working months or years ago.  The application might have given you a notification in the system tray. You promised yourself you’d get to it, but you never did.

Or, let’s say it’s an online backup service, and you had it set for automatic renewal on your credit card. But then your credit card expired, and you forgot to update it with the backup company.  Does anyone proactively update this stuff?  The online company probably emailed you many times.  It either ended up in your spam filter, or it got missed along with all the marketing emails (this is why I prefer paper billing).  This happened to me recently.  I was looking for an email and noticed I had been warned about an expiring credit card.  I missed it.  While I didn’t have a data loss during the gap period,   others aren’t as lucky


If you’ve installed backup software, read the terms carefully.  Sometimes the software is just a limited trial. If it’s a trial, either buy the software or don’t install it.  Commit to a backup solution and stick with it.  If you’re using an online backup service, that’s the account to update when you get a new card.  I’d also put a reminder when it’s set for renewal. That’s when I start looking for deals on renewals too. Put it on your calendar, or use an app like Bobby to help remind you.

3. You Aren’t Backing Up The Right Stuff

Your backups aren’t going to expire, and you can get into them, but those are not the only settings to consider.  To save space and bandwidth, your backup solution may not handle everything.  For example, it might exclude large files or external drives.

A great example of this problem is Quickbooks’ tendency to store its data files in the Public folder on a PC.  The typical backup software backs up the user folder and misses the public areas.  Another example is program preferences. They’re stored either in the system directory or the application directly—both are often skipped by the default settings of backup programs.

You’re probably fine if you’re using cloning software on a PC or Mac.  This problem presents more often with online backup solutions. Even if you try marking these folders, some online services won’t do it.  That’s one reason to have both a local cloned backup and an online backup.


Go into your backup software’s settings and review what it’s backing up.  Review what’s in the folders it isn’t backing up and see if anything’s in there of importance.  Don’t make this a one-time thing, either.  Consistently audit what your online or local backups include.  We’ll talk about testing later, but part of testing is seeing if your software changed something.  When my online software updated and I did a reinstall, my settings were reset.  I didn’t realize until my testing that it was excluding .iso and .dmg files.  For most people, that isn’t a problem.  I need these files because I have a vast archived software library for testing.  They’re the hardest to find should disaster occur.  You’d be surprised how hard it is to find Windows for Workgroups 3.11.

4. You Don’t Realize The Limits of Your Backup Solution

The goal of a backup program is to protect your stuff.  Your stuff is the stuff you create.  You didn’t create your operating system unless you work for Microsoft or Apple.  But in many cases, you’ll want that operating system backed up, too. Or, you’ll at least want to have the ability to install your operating system and all your applications again legally. You’ll either get a new computer or reinstall your operating system in a disaster.

Most people address this issue by using a cloned backup system. A full cloned backup includes the operating system and all your installed programs.  Most other solutions just back up your data—the stuff you made.  Things like pictures and documents.

But even if you have a cloned solution, programs might detect changes to your operating system or hardware and ask for a serial number or password.  That verification is a form of copy protection. What would stop you from cloning your expensive software installation to multiple computers?  If your hard drive dies, you’ll either get a new one or a new computer.  Either scenario could trigger a verification.

Backing up installers and programs adds to the size of your backup set, which raises another backup limitation: how long it takes to restore your data. One problem with online solutions is the time it takes to download a full restore. First, the online company has to prep your restore.  The more data, the more time it takes.  Recently I did some testing (see below about testing), and my 100 GB file took about 6 hours for them to spin up.  Then it took a day or so to download it.  If I needed that stuff to get up and running, that would be an unacceptable delay. Some companies, like Backblaze and CrashPlan, will overnight you the data at a hefty price.


First, keep track of the serial numbers of all your programs.  I keep mine in 1Password, but even a simple spreadsheet would suffice.  That spreadsheet can be in your data folder with your backup solution.  In either case, record the location of the software.  Sometimes you’ll need to reinstall it.  If the software is located online, you’ll need, wait for it, your passwords.  If you forget those passwords, you might be in the same dilemma as the first problem.  Password resets work only if you can remember and have access to your old email accounts.  I keep .iso and .dmg images of all my installers.  In the folder or comments for the file is the serial number to reinstall it.  Those folders then get back up unless I miss the defaults like in the previous example I gave.

If you aren’t cloning your drive, make sure you have installers for all your software.  You’ll need either physical copies or electronic images.  Along with those are some ways of reinstalling your operating system.  We’ve covered ways of downloading an image of Windows 10 and older versions of Windows as well as macOS.

If you’re using an online backup system, consider a local cloned backup on occasion.  Then you’ll only have to download the changed files.

5. The Unforgivable Mistake: Not Testing Your Backups

All these examples lead to the importance of testing.  If you test your backups regularly, you’ll avoid all these problems.  You’ll know what’s backing up and how to get to it. When you do a test, you’ll catch all the problems with passwords, defaults, and limitations.  I like to do testing when the clocks change.  You check your smoke detectors at that time. Smoke detectors protect your house from burning to the ground.  Backups prevent your data from burning down to the ground or at the very least, disappearing.

Photo by Camdiluv ♥


Create a checklist of your most important stuff.  That’s the stuff you’d pay data recovery companies thousands of dollars to get back.  For me, that would be my pictures and my Quickbooks file.  I can’t test restoring all my pictures, but I can do a random sample of pictures.  I usually pick a few dozen and restore them.  My thoughts are that if it got some of my pictures, the backup got them all.  This testing is the time I make a complete cloned image of my drive too.  That way, in a disaster, I’m up and running.  I check my 1Password and make sure my software serial numbers and links to download software in there.  Total time:  15 minutes.

Isn’t 15 minutes worth saving years or a decade worth of data?  You might be losing an hour for daylight savings time.  That’s a pain.  Imagine all the time you’ll lose without a reliable backup.

Got a backup strategy horror story? Share it in the comments and help others avoid the same mistake!

Bonus Tip: Syncing Isn’t the Same as a Backup

As a reminder, online syncing services like Dropbox, Box, and SugarSync don’t qualify as a backup.  They’re only syncing the data in their respective folders.  If it’s outside of the synced folders, it’s at risk.  It isn’t a true backup, even if you keep all your important stuff in a synced solution.  A synced solution can lead to data loss.  You delete it from one folder, and it deletes all your devices.  These services offer limited archiving, meaning you can get the data back.  The problem is you need to realize it before the archiving/versioning limit. If you miss it outside that period, your data is gone.  If your account gets hacked and someone deletes all your stuff from all your computers, you’ll have trouble getting it back.  Since syncing can destroy data, it’s not a backup solution in my book.



  1. Alan

    Although I believe the article was written with the best intent, the title needs to be re-worded: “The 5 Backup Strategy Mistakes You’ve Already Made”

    Are you assuming that everybody is stupid? When I read the article I havnt made ANY of the 5 Mistakes Ive Already Made.

    A simple reword of the title would make the article a lot less of an attack on users abilities……

    • Jack Busch

      Sorry for the presumption, Alan! I came up with that title after reading the article and realizing I had done most of them. I don’t consider myself (or anyone else) stupid in spite of that :)

    • Dave Greenbaum

      I’m sorry about that as well.

      As Jack said, that was not his intent at all.

      However, people that are diligent about backups usually experienced a data loss at some point. That’s why they’re so cautious. Is my theory true in your case? What inspired you to be so good about this!

  2. Albert van Huissteden

    My data loss is limited to photos, I backed up everything to a 1000 GB external hard drive, pretty save heh. The hard drive went on the blink and I lost everything.

    • Dave Greenbaum

      Ouch! If I had to pick a sixth thing, it would be having backups in more than one place! However, testing might have prdicted the hard drive failure.

  3. Allen

    Backing up online. Old guy who’s leary of saving my data (of little value to others, but…) “online”. If I were to go that route, how could I insure that my backup is mine only? And are there services that would send an email notification that one’s contract is about to expire?

    • Steve Krause

      Hi Allen,

      My favorite service for backup (as you can see from my recommendation page) is Crashplan. It allows you to set a password which encrypts the data prior to sending it to them for backup. This means, only you have the key.

      This is both good and bad. Just don’t lose the password!

    • Dave Greenbaum

      I use both Crashplan and Backblaze on different machines. Both are great products. I think Backblaze has an easier (although less configurable interface). One advantage, I believe, to Backblaze is you can set up two-factor authentication so that if someone gets your password, they still can’t get to your stuff.

      Both companies send you an email that your account is set to expire and give you a grace period in case your credit card expired or changed. You can also set it to auto-renew so your card is charged each year without your intervention.

  4. kbutler

    So I have tried them all, and always return to cloning the drive which I want backed up, whether iit is a physical or logical drive. EASEUS has several programs – I use Partition Master, now Ver.10.8

    Don’t be cheap, pay for the lowest price version of whatever you get. Their technical help is good, and prompt. OK, the plug is over.

    The plan I use should involve 3 separate clones of each drive, grandfather, father, son. Always overwrite the oldest of the 3 when you backup. Keep a regular schedule and use good hardware. 1TB laptop drives are cheap. In most cases I backup at night, overnight. Keep the backup drives in a safe place, do not carry them with you all the time or leave them lying around in the open.

    Final rule: NEVER clone a partition (what you see as C, E, etc)to another partition on the same physical drive. I’m using a laptop with one physical drive partitioned into two logical drives, C & E.

    Frequency of the backup’s up to the user but you need to decide: How much of my most recent information can I afford to lose? OH, yeah — don’t get caught in the loop of differential backups. That can turn into a quagmire uncle Wiggley couldn’t get out of.

    • Dave Greenbaum

      Cloning is good, but don’t you find it a problem if you attempt to use the clone on a new machine? Windows isn’t terribly forgiving about that.

      • kbutler

        Yes and NO. I keep all data files and special configuration files on my “E” drive. Cloning that is easy. Now that I am using Windows 10, when I clone “C”, the system drive I have to be sure to clone the boot partition as well. So far no fail. I should also acknowledge recent use of Easeus Turbo Backup for both C & E. No problems accessing those files later from Turbo Backup and restoring or just reviewing them. Still use the 1-2-3 pattern.

        At my before retirement job I administered a pc-based multi-user live database, SQL. The database was backed up several times a day to its native partition with the SQL backup available with Microsoft SQL, the employer’s standard. Daily AND AFTER HOURS the last backup of the day was copied to another machine not part of the multiuser network. Each days offline copy was kept through 30 days, then deleted. The daily backups simply overwrote the daily backup from the previous day.

        When a system crash took out the SQL server raid drives the IT department restored their backup copies which were ” the official copies and the only backups they would or could restore.” The restored files were 2 months old, their tape drives had been failing every night. Work lost:over 2 months, no records from IT, student’s payment records lost.

        I pulled my most recent backup copy to restore. Final data loss was just a few records and a few hours. I no longer depend on others, if I screw up I only blame myself.

        Boy, I get blamed a lot, lately, but as I exemplified above I have been bitten before (more times then I can remember) so I try to be precise and complete.

        Now that I made you read all of that, data restore problems: NO system restore problems: few and seldom. You just need to get into a strong habit.

        Thanks for replying & reading

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