Become Tech Savvy: How to setup automatic backups in macOS and iOS

First time checking out this series? You’ll get the most value by starting with the first article and here is the series overview.

Note for regular readers, the already tech savvy, and IT professionals: this is designed as a resource you can give to those you are helping or for those looking to become tech savvy on their own.

Priority #1: Setup automatic backups

Background, Expectations, & Best Practices |

So far we’ve covered why you can and should be tech savvy, how to get in the right state of mind, and how to transform your limiting beliefs and set some stakes as you work towards the goal of using technology with confidence and ease. These aspects are the hidden forces that hold us back from achievement, so with all of them addressed we’re all set to move forward with strategy.

Like I mentioned in the last article, I’ve created the Become Tech Savvy strategy with Tim Ferriss’ DiSSS approach. The intentional design of deconstruction, selection, and sequencing of this series is what makes it unique and will give you results.

Priority number one is to implement a solid backup strategy. If you’re not familiar, a backup is a copy of your digital information in case the original is lost, damaged or a device or drive has failed. This is not only the top priority because of the potential loss of your valuable photos, videos, documents, or other data, but also because our backup preparedness shapes how we interact with technology.

Because you will see major positve results from this priority and next week’s topic, password managment, they will take more effort to jumpstart and implement than most other topics we’ll cover in this series. Don’t worry though, we’ll walk through the how-to into achievable chunks and provide more tips for success in the Do This section below.

Why Backup? |

Did you ever play the the NES game Contra and use (or hear about) the cheat code ↑↑↓↓←→←→BA? Just in case you haven’t, using this code would give players 30 bonus lives. This example illustrates how changing the rules can effect how we play a game and change the outcomes.


With the example of adding 30 lives to a video game, think about how you would play differently. You’d have confidence would be boosted, and you’d likely take more risks to innovate, explore, and improve. This concept applies to how we approach and use technology on a bigger scale as well.

One of the most common responses I hear to questions like ‘have you tried this?’ is ‘I’m afraid I’m going to mess up my device.’ This hesitation or fear often limits the exact experience and exposure we need to move past these anxieties. Having the safety net of a strong backup strategy alleviates these concerns and gives you the freedom and confidence to try new things and build your skills.

The other chief reason to backup properly is that all electronic devices are machines and will fail eventually. The trick is that we never know when. Although it’s tempting, we can’t use past device performance to predict future results. You might have zero issues with multiple machines and your next shiny new one could fail in the first year. There are no guarantees.

‘Two is one and one is none’ is a good rhyme to help remember the importance of keeping multiple backups. Including the information on your device and your backups, you should have a minimum of 3 copies of your data. I don’t think I’ve seen people more frustrated in life than when they go to restore their data from a backup and their only backup fails. If you have highly valuable data keeping one of your backups off-site (cloud service, bank box, or friend’s house) is best in case of fire, flood, other natural disasters, as well as theft.

What & How |

For now, we’ll discuss two different common types of backups. The more traditional option is an automatic local backup. The second option is an automatic cloud backup. You don’t have to pick just one either, many people use both options. Local means that the backup is being stored on a device (usually external hard drive) that you have. Cloud backups, on the other hand, are saved off-site on an Internet connected server, which you have access to (similar to a storage unit rental).

My guess is that a much higher percentage of people would save their information if they got an automatic backup solution in place first, so that’s what we’ll start with. You can manually manage backups as well, but we’ll cover that in another post as automatic backups will give us the most bang for our buck.

Automatic Local Backups for Macs |

The best way to set up an automatic local backup is with the Time Machine software that’s already built-in to your Mac. Once configured properly, your Mac will backup hourly for the past 24 hours, daily for the past month and will save a weekly backup for all previous months to an external hard drive or external SSD (solid state drive). We’ll cover more about hard drives, solid state drives, and USB thumb drives in the future.

You can use most any external hard drive, but it will need to be formatted for macOS if it didn’t come that way from the manufacturer. If you don’t have an external hard drive, this 1TB (1,000GB) option by Seagate is great for $60. It’s plug and play ready, doesn’t need an external power source, and has a large enough capacity for most people (check how much storage you’re using by clicking in the top left  → About This Mac → Storage). They also offer 2 and 4TB options.

The only reasons your Time Machine automatic backups will stop is if you turn it off manually, eject/unplug your external hard drive, or turn off your computer. If you turn your machine off regularly or use a MacBook, your backups will continue automatically when you plug your external drive back in and your machine is on.

The beautiful part about Time Machine is that it will keep backing up your new information even if your drive fills up, in which case it will delete the oldest backups.

It’s important to know that Time Machine clones your entire computer, all the files, applications (programs), photos, videos, preferences, etc. and it stores it in the form of a backup package. These Time Machine packages are not meant to be pulled apart or used for browsing your content (if you want to drag and drop files back and forth and browse your data, we’ll cover this in a later article).

A Time Machine backup’s main purpose is to restore a computer with all of your information exactly how it was in the event of a lost, failed, or damaged Mac or when upgrading to a new Mac.

Here’s how to set up an automatic backup with Time Machine on your Mac with an external hard drive:


When you plug your external hard drive in for the first time, this dialog box will appear (external drives that don’t need a power source will power on automatically when plugged in, hard drives that use an external power source may have an on/off switch). Click Use as Backup Disk.


You’ll notice in the middle area of the Time Machine window that your backup will start automatically. The Back Up Automatically box will be checked by default.


You can also check the Show Time Machine in menu bar at the bottom of the Time Machine window to have quick access and control to Time Machines settings and info. You can choose to Back Up Now if you don’t want to wait for the next scheduled one.

You may also notice if you are using a MacBook that the automatic backup may not start until you plug in your power adapter.


Once your backup has started you’ll see the details of your backup and a time estimate (take the estimate with a BIG grain of salt. This backup estimated 14-19 minutes, but it ended up actually taking 2 hours).


When your backup is complete you’ll see it in the Time Machine window as well in the menu bar. If you ever need to get back to Time Machine preferences and don’t have the menu bar option turned on you can find it by clicking top left of your Mac  → System Preferences → Time Machine.

Automatic Cloud Backups for Macs |

A cloud backup is stored on a remote server instead of being stored on an external hard drive or device that you have. We will deconstruct and build a greater understanding of cloud services in general in articles to come, but for now we’ll focus on cloud backups specifically.

Automatic cloud backups for your Mac are usually a paid service. Crash Plan and Backblaze are two examples of reputable automatic cloud backup services for Mac (and other platforms as well). Both services have free trial options and costs starting at $5/month (there are other ways to do this, but they often become more complex).

One of the biggest benefits of these services is once you get them going you don’t have to worry about them at all and if you experience any natural disasters or theft, all of your information is safe.

Automatic Cloud Backups for iPhone, iPad and iPod Touch |

This option will happen automatically by utilizing software built-in to iOS (the operating system that iPhones, iPads and iPods run). These backup are setup through iCloud on your device and stored on Apple’s servers. You can access almost any of your data (depending on your settings) at or any Apple device on which you’re logged into iCloud.

Here’s what it looks like to make sure your iPhone, iPad or iPod has iCloud Backups turned on and will automatically continue to do so:


Make sure you are connected to Wi-Fi and then locate and select Settings on your device. Scroll down until you see iCloud and tap on it.


Scroll down again until use see Backup and tap on it. Your screen should look like the image above. If the toggle to the right of iCloud Backup is not green, tap on it to turn it on. Below you have the option to Back Up Now and below you’ll see a timestamp with your last backup.

Once iCloud Backup is turned on, your iPhone, iPad, or iPod will automatically backup any time it is charging and connected to Wi-Fi with the screen locked (your screen is locked when you press the sleep/wake/power button on the right side of your iPhone 6/6 Plus or later or on top of your device for iPhone 5s, iPad or iPod Touch).

Usually the only other thing to watch out for is running out of iCloud Storage. Apple includes 5GB for free, but this often doesn’t last too long. They offer 50GB for $1 a month and it’s definitely worth it (think about much your phone bill is, this is only $12/year to protect your information 🤓). Here’s how to check how much iCloud Storage have and upgrade it if needed:


Navigate back to Settings → iCloudStorage. Now you should see Change Storage Plan, tap on it and you’ll see the Current Plan that you’re on a the upgrade options. 50GB will be perfect for most people, but they have larger plans if you have a large media collection.

Semi-Automatic Backups for iPhone, iPad, and iPod |

This option is if you’d like to save your iPhone, iPad, or iPod backups to your Mac or PC via iTunes. The reason it’s semi-automatic is that you have to remember plug in your phone for it to back up automatically or if you use the Sync with this iPhone over Wi-Fi you’ll need to have iTunes open on your computer. Here’s how to setup backups for iOS devices with iTunes:


Plug your device in to your computer with the Lightning to USB cable. You’ll soon see this prompt, select Continue.


If you haven’t synced or backed up with iTunes before you’ll need to tap Trust on your device.


iTunes should launch automatically (if not open it manually Finder → Applications → iTunes). Click the device icon in the top left hand area. In some cases you may need to update your iTunes software (click iTunes → Check for Updates).


Once you’ve made it to the Summary window of your device in iTunes like pictured above, make sure the boxes are checked for Automatically sync when this iPhone is connected and Sync with this iPhone over Wi-Fi. To save, click Apply in the bottom right corner.

With these two settings turned on you’ll get semi-automatic backups. The first way is anytime you plug in your device to your computer it should launch iTunes and complete a backup, the second is anytime your phone is charging and on the same Wi-Fi network as your computer that has iTunes open it should also backup automatically.

You will see a timestamp with your most recent backup to your computer on the middle right of iTunes. You can also choose if you would like to automatically sync with iCloud or This computer as the default in the middle left area of iTunes. 

Do This |

1.  If you haven’t already, choose at least one of the options above for each of your devices and get automatic backups setup and the first one completed.

2.  Ask for help from someone you trust if you need help setting up and understanding automatic backups. If and when someone does help you, make sure you ask them to take their time and explain things you don’t understand. If there is someone who can help you but you don’t live near them, you can use this resource to screen share with them.

3.  Don’t hesitate to call AppleCare support. They often times will help at no cost even if you are out of warranty at (no guarantee). They are consistently rated the best tech support in the industry and can even screen share with you in certain cases to see what you’re seeing. You can even tell Siri ‘I need Apple Support’ and she’ll get you to the Apple Support page.

4.  Set a reminder for no longer than a week to re-visit how you setup automatic backups for your devices and verify that they are still working and have updated since the first backup.

5.  Since there’s a lot of options and possibilities when it comes to backing up please ask any questions in the comments section below. There is a lot more that can be covered, but to make this first priority as digestible and doable as possible I wanted to keep it more limited.

Troubleshooting/Solution Seeking |

  • I want to see what’s stored on the cloud. Automatic cloud backups are a mirror of what’s on your device for iPhone, iPad and iPod. If you delete something from your device, it will also be deleted from the next backup. So in most cases unless you are using iCloud Drive to save files and content manually, what you see on your phone is the same thing that’s stored in your iCloud Backup.
  • I bought more storage and I’m still out of room. The option to buy more storage is only for iCloud Storage which is what will mirror (backup) your phone. If you keep seeing Storage Almost Full, you’ve used up the storage of your device itself. Go to Settings → General → Storage & iCloud Usage → Storage → Manage Storage to see what’s using the most space. Remove what you can, if important save content from your phone to a computer first, then delete.
  • I’m out of iCloud Storage. In the ‘Automatic Cloud Backups for iPhone, iPad, and iPod there is a walkthrough on how to buy more storage. Alternately you could delete old backups (from old devices you may no longer have) by going to Settings → General → Storage & iCloud Usage → ICLOUD → Manage Storage → BACKUPS → Select a device that doesn’t show as This iPhone or This iPad. Check the date to make sure you’d like to delete it. Tap Delete Backup.
  • I have plenty of storage on my phone and in iCloud and it still won’t backup. In some cases iCloud may experience glitches and signing out of iCloud and signing back in will solve the problem. Go to Settings → iCloud → Sign Out (very bottom) → Sign Out → ‘All iCloud notes will be removed from your phone’ tap Delete from My iPhone → Keep on My iPhone. Following  these steps won’t delete any information from your iCloud account but rather just remove (delete) it from this particular device until you sign back in. Once you’re signed out, sign back in and start an iCloud Backup. See walkthrough above if needed.

Next Week: Password Management

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