• Make sure the folders are named identically and are in two different locations on your Mac.
• Press and hold the Option key, then drag the folder that contains more files to the location that contains the folder with fewer files.
• In the dialog that appears, click Merge to copy only newer files from the source and those not already in the destination. (It’s not a two-way sync; for that, you need an app like ChronoSync.)

The Merge button appears only if the source folder contains files not in the destination; if the folders contain just different versions of identically named files, you’ll get only Stop and Replace buttons. For safety, always work on copies of your folders and check your work afterward to ensure the right things happened. When you’re satisfied all’s well, you can delete the duplicate folders. 

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1. Update your old iPhone to the latest version of iOS. If you have an Apple Watch, update it to the latest version of watchOS. This process can take some time, so it may be best done overnight before you move data to your new iPhone.
2. Make sure you know your Apple ID and password, and if you have an Apple Watch, its passcode. You will likely have to enter them at least once during this process.
3. Make a backup of your old iPhone to iCloud or your Mac. (If you back up to a Mac, be sure to encrypt the backup, or else it won’t include saved passwords, Wi-Fi settings, browsing history, Health data, and call history.) Or back up to both, for safety’s sake. We prefer iCloud backups because they’re easier and don’t introduce additional variables, like flaky USB cables. Apple will even give you temporary iCloud storage to make a backup when moving to a new iPhone. To initiate an iCloud backup, go to Settings > Your Name > iCloud > iCloud Backup and tap Back Up Now.
   
4. If you have an Apple Watch, you shouldn’t have to unpair it from your old iPhone to transfer it to the new one, but if the automatic transfer doesn’t work, you can unpair it manually and pair it again later. (If you take the manual route and have a cellular Apple Watch, you’ll be asked if you want to keep or remove your plan. Assuming that you’re keeping your Apple Watch to re-pair with your new iPhone, keep the plan.)
5. You shouldn’t need to worry about transferring a SIM card. If you order through Apple and connect to your cellular carrier account during purchase, activating the new iPhone should cause it to take over your phone number. The same should be true if you purchase directly through your carrier. Besides, it’s likely that iPhone 15 models sold in the US will rely on eSIM and lack SIM trays like the iPhone 14, so only non-US users might need to transfer the SIM card from the old iPhone to the new one. Even then, it’s better to contact your carrier and get them to activate the new SIM in the new iPhone because old SIMs don’t always support all current cellular features, such as full 5G support.
6. Transfer your data, settings, apps, and purchased content in one of these three ways. None of them will be quick, despite the first one’s name, so do the transfer when you have time:
   • Quick Start: With the Quick Start feature, content from your old iPhone copies directly from your old iPhone to your new one. We recommend this technique because it’s more likely to preserve app logins, something that’s less true when restoring from an iCloud backup. Put your iPhones next to each other (plugged into power), use the old iPhone to scan the animation on the new one, and then follow the rest of the steps.
     
   • iCloud: With this technique, the new iPhone will download your content from your old iPhone’s iCloud backup. Once you’ve joined a Wi-Fi network on the new iPhone and tapped the Restore from iCloud Backup button, you’ll have to select the correct backup—likely the most recent one you just made. Keep your new iPhone plugged into power the entire time to ensure that all your content syncs during this step.
   • Finder or iTunes: With this approach, you’ll restore your old iPhone’s content from a backup made to your Mac. Connect your new iPhone to your Mac using an appropriate cable, open a Finder window (or iTunes on an old Mac), select your device, click Restore Backup, and choose the appropriate backup—likely the most recent one.
7. Perform post-transfer tasks. Ensure that you can make and receive a phone call. If necessary, pair your Apple Watch with the new iPhone. You’ll also need to pair your Bluetooth accessories—including AirPods—with your new iPhone. Plus, some app data needs to sync to your new iPhone, so open the Mail, Contacts, and Calendar apps and check if they have your data. It could take a few minutes for them to fill up. Apps may request notification permissions again, and you may need to download content and in-app purchases.
8. Finally, and this post-transfer task is becoming increasingly important, if you use two-factor authentication with an app like 1Password, Authy, or Google Authenticator, ensure you can get your 2FA codes using your new iPhone. 1Password and Authy are good about providing access to your 2FA codes from multiple devices—just log in to your account from each device—but Google Authenticator may require some additional setup since it didn’t originally offer any way to transfer codes to a new phone.

Although Apple works hard to make the process of transferring from an old iPhone to a new one as painless as possible, some things may fail to transfer seamlessly. For that reason, we strongly recommend holding onto your old iPhone for a week or so to ensure the new one can do everything the old one could. During that time, put the new iPhone through its paces with an eye toward checking every app you need.

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There’s no avoiding some downtime when installing a full macOS update, which is why we recommend starting such updates at the end of the day or before you leave for lunch. That’s why Apple introduced Rapid Security Responses, which generally install in just 3–4 minutes, including a restart if necessary.

But with a bit of setup, you can pick up where you left off before a restart within a minute or two. There are three settings that can reopen apps, documents, and folders, and all Web browsers have options that reload all previously open tabs.

Apps, Documents, and Folders

If you always want certain apps running or documents open, you can ensure they open at login. In macOS 13 Ventura, open System Settings > General > Login Items (shown below); in macOS 12 Monterey and earlier, look in System Preferences > Users & Groups > User > Login Items.

You can add apps, documents, and even folders to the Open at Login list. To remove an unwanted item, select it and click the – button. If there’s anything you don’t recognize, Control-click it and choose Show in Finder to see where it’s located.

What if you have other apps or documents open that you want to return to immediately after relaunching an app? macOS offers another setting for that. In Ventura, look in System Settings > Desktop & Dock and scroll down to Windows & Apps. Deselect “Close windows when quitting an application” because reopening an app won’t restore its open documents and windows when that’s on. In Monterey and earlier, find this setting in System Preferences > General.

Choose Restart, Shut Down, or Log Out from the Apple menu to reveal the last and most important setting to ensure that your Mac environment is the same after a restart as it was before. In this dialog, select “Reopen windows when logging back in” and click Restart. macOS remembers this setting, so you shouldn’t have to select it each time.

As a bonus, if your Mac crashes or shuts down unexpectedly, it should come back as it was before the crash.

Web Browsers

The macOS settings above should work for most apps, but Web browsers are a special case. Open tabs aren’t quite the same as documents, and you might or might not want all those tabs to come back after relaunching your browser. Control the session settings in these popular Web browsers with the instructions below:

• Safari: Recent versions of Safari always open with windows (and tabs) from your last session, though you can choose whether that includes all windows or just non-private ones in Safari > Settings > General.
  
• Google Chrome: For Google Chrome, you have additional options, but to make sure your open tabs are restored after relaunching the app, choose Chrome > Settings > On Startup, and select “Continue where you left off.”
  
• Firefox: Mozilla’s browser puts its session settings front and center. Choose Firefox > Settings > General and select “Open previous windows and tabs.”
  
• Arc: The new browser Arc encourages users to set up workspaces containing pinned tabs, both of which persist across sessions. However, to ensure all your windows and regular tabs load after relaunching, open Arc > Settings > Advanced and select “When opening Arc, restore windows from previous session.”
  
• Brave: As a Chrome-based browser, Brave offers a setting similar to Chrome but in a different location. Find it in Brave > Settings > Get Started.
  
• Microsoft Edge: Although it is also based on Chrome, Microsoft Edge stores its session setting in a different location, with a different name. Choose Microsoft Edge > Settings > Start, Home, and New Tabs, and then select “Open tabs from the previous session.”
  

Between these macOS and browser settings, you can ensure that a restart presents the minimum interruption possible, such that when your Mac finishes restarting, all your apps, documents, windows, and browser tabs will be the same as when you left off.

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All cloud storage services provide a simple Web-based interface that’s the least common denominator. The Web interfaces look and work the same for everyone, regardless of platform. Unfortunately, they’re clumsier—sometimes much more so— than working with the same files in the Mac’s Finder.

Luckily, cloud storage services also provide deep integration with the Finder. If you haven’t already installed your cloud storage service’s Mac app, we strongly encourage you to do so. Here are links for the big four; others will likely provide similar apps.

• Box Drive
• Dropbox
• Google Drive for Desktop
• OneDrive for Mac

Once the software is installed, you’ll find an item in the Locations portion of your Finder window sidebar that provides access to everything in your cloud storage, as though it were on an external hard drive connected to your Mac. You can quickly rename files, add folders, move files between folders, and perform other basic Finder tasks. The services also install menu bar items you can click to access settings, activity, and other controls (Dropbox shown below).

Cloud storage is not the same as an external hard drive, of course, so you need to keep certain facts in mind when using cloud-based data in the Finder. Some of this information has changed within the last few months, as cloud storage providers have migrated from Apple-deprecated custom kernel extensions to Apple’s recommended File Provider extension. (The migration is still underway for Dropbox users.) Here are the most important things to know.

Data May or May Not Be Stored on Your Mac’s Drive

When integrating a cloud storage service into the Finder, it’s reasonable to ask where the data is actually stored. The short answer is that it’s always stored online, but it might also be stored on your Mac. All cloud-based files are either online-only, at which point all you see is a placeholder icon on your Mac, or offline, which means a copy of the files exists on your Mac. Online-only files and folders have a little cloud icon next to their names in the Finder; offline files lack that icon.

When you double-click an online-only file, the service’s Mac software downloads it in the background so it can open in the appropriate app. You shouldn’t notice a delay with small files, although it may become more noticeable with very large files or over slow Internet connections. And, of course, if you’re on an airplane or somewhere without connectivity, you can’t open online-only files at all. On the plus side, they don’t take up any space on your Mac’s drive until you open them.

You can control which files and folders are online-only and which are offline. Control-click the file or folder and look for commands like Download Now or Make Available Offline to bring its contents down to your Mac, or use commands like Remove Download or Make Online-Only to remove the download to save space.

All Your Files Live In ~/Library/CloudStorage

So where are the offline copies of cloud-based files stored on your Mac? It may seem like they’re on a drive of their own, but in reality, they’re stored in your home folder’s hidden Library folder, in a folder called CloudStorage. (To see the Library folder, open the Finder’s Go menu and press Option.) You never have to go there directly, but it can be useful to keep in mind when setting up backups, moving data between Macs, and more.

Only OneDrive Supports External Drives

There is an important caveat to the requirement that all cloud-based files live in ~/Library/CloudStorage. That folder lives on your Mac’s internal drive, which may not have sufficient space to store offline copies of all your cloud-based data. Before the switch to Apple’s File Provider extension, the cloud storage services let you store the offline copies of your files on an external hard drive. That’s no longer possible with Box, Dropbox, and Google Drive. Microsoft OneDrive has worked around this limitation, allowing you to specify an external drive as your cache to maintain a copy of offline data separately from the state of the items in the CloudStorage folder. (If you manage terabytes of offline files, particularly for audio or video editing work, check out the completely different LucidLink service.)

Dragging Files Moves Rather than Copies

When you work with an external hard drive or network drive, dragging a file from your Mac’s internal drive to one of those copies it because it’s going to a different volume. Although the cloud storage services seem to be separate volumes (some were in the past), they no longer act that way. That’s because all the data lives in the CloudStorage folder on your internal drive, so dragging a file out of Google Drive, say, moves it, just as though you dragged a file from one folder on your internal drive to another. It’s not a problem—and the services warn you about it—but keep it in mind.

Moved or Trashed Files Remain Available Online, at Least Temporarily

What happens to the online version of a file when you move it from the cloud storage service on your Mac to another location on your Mac’s internal drive? Good question, and the answer is that it ends up in the trash equivalent on the service’s website. Cloud storage services generally retain such files for some time—30 days is common—after which they go away for good.

When you delete a cloud-based file in the Finder, the same thing happens: it ends up in the service’s online trash equivalent. However, what happens on your Mac varies by service, so testing with a sacrificial file is worthwhile. For example, if you delete an offline file in Dropbox, it moves to the Mac’s Trash. However, if you delete an online-only file, Dropbox warns you that it will be deleted immediately, and it disappears instantly from the Mac rather than moving to the Trash. You can still find it in Dropbox’s Deleted Files folder on the Dropbox website. In contrast, deleting either type of file from Google Drive moves it to the Mac’s Trash (and puts it in Google Drive’s online Trash folder).

Sharing Files and Paths with Colleagues

All the cloud storage services let you Control-click a file and copy a link. When a co-worker clicks that link, it will open in the cloud storage service’s Web interface or possibly in an online version of the app that created it. That may be fine, but our experience is that they won’t be able to find the file again in the future.

To help colleagues learn where files are in a shared cloud-based folder structure, send them the path to the file—the full list of folders containing the file. The trick for getting it is to select the file in the Finder, Option-click the Edit menu, and choose Copy “MyFile” as Pathname.

The start of the path is specific to your Mac, so delete that and leave the rest. For instance, when you paste the path, if you get this:

/Users/foobar/Library/CloudStorage/GoogleDrive-foobar@example.com/My Drive/GroupShared/Buzz/Posts/Buzz-0004.pdf

Trim it as follows to clarify that the file is in the Posts folder, which is in the Buzz folder, and that’s in  a top-level folder called GroupShared:

/GroupShared/Buzz/Posts/Buzz-0004.pdf

Searches May Work Poorly for Online-Only Content

The split between online-only and offline files also affects how Spotlight and other content-based searches work. As you would imagine, if a file is online-only, there’s no way Spotlight can index its content, so Spotlight won’t be able to find such files based on content searches. Some of the cloud storage services offer content-based searches, so with Google Drive, for instance, if you initiate a search from its Web interface, it will find all files containing the search terms even when they’re set to online-only on your Mac.

Filename searches in Finder windows should work regardless of online-only/offline state, although we’ve experienced problems when trying to limit the scope within the service’s Mac folder—search the This Mac scope for the best results. (Click the This Mac button after starting the search if necessary.) You may also have good luck with third-party search utilities like EasyFind and Find Any File.

Backups Work Only for Offline Content

Finally, remember that Mac backup systems like Time Machine and Backblaze cannot back up online-only files because they don’t actually exist on your drive. At best, such backup apps will show the placeholder for the file but won’t back up its content. They work fine for offline files, of course, but if you have to find a particular file or folder when restoring, remember that backup apps other than Time Machine will probably see it as stored in ~/Library/CloudStorage.

Should you care if your cloud-based files are backed up locally? Cloud storage systems automatically protect data against drive failure or other problems in the cloud. Plus, any shared data that one of your collaborators deletes from their Mac—inadvertently or maliciously—should be maintained in that person’s online trash, even if it seems to disappear.

However, we’d argue that it’s all too easy to lose or corrupt cloud-based data such that you want a local backup. We’ve seen too many situations where cloud-based files went missing or had problems. In those cases, a local backup provided an essential fallback or welcome peace of mind.

To ensure that your cloud-based files are backed up alongside your other files, you must make sure they’re stored offline long enough to get into your backups. Select top-level folders, make them offline, and wait until everything has downloaded and been backed up. If you need the space back, you can return some folders to being online-only. Pay attention to new files added by other devices or people since they may be online-only by default and thus fail to be included in your backups.

For backup of an organizational cloud storage account, it might make more sense to use a service like Backupify, CloudAlly, or CubeBackup, or to rely on something like a Synology NAS device with Cloud Sync. But that’s a topic for another day or another discussion—get in touch to learn more.

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#1: Start Now and Catch Up Later

Don’t let your old files prevent you from starting a new organizational approach. The best time to begin is now; you can reorganize old files later.

An easy way to avoid being bogged down by old stuff is to move all your existing files and folders into a folder called “Unorganized” at the top level of wherever you store documents. Make sure to retain any hierarchy that those old files might have. If you’re still working with those files, they remain just as accessible as they were before.

One type of cleanup is often worth doing right away: If you have a lot of temporary or duplicate files from past projects that you can instantly identify as unnecessary, delete those now while they’re still familiar. That saves you or someone else the work of thinking about them again in the future.

#2: Pick an Organizational Structure

The most important question to ask yourself or your colleagues is what sort of organizational structure matches how you think about your data. There are four common approaches:

• Project name: It’s hard to go wrong with using a project name as your primary organizational structure. For instance, an ad agency might have a top-level folder for each client, or a book publisher might have one for each title. A nonprofit that organizes five annual events could have a folder for each event. Within each project folder, additional folders can separate files by category. You may also add some date-based structure to keep older files from getting in the way of current work. For instance, here’s how an ad agency might organize email marketing files for a hotel.
  

• Date: Groups with many files that revolve around time periods may find it easiest to organize everything by year, month, and day. Date-based organization is a special case—you’ll know if it makes sense for your data and usage patterns. For instance, if a distributor creates different inventory reports for every supplier every day, a hierarchy like this might make working with files from the same time period easy. However, finding all the files for a particular supplier would be more difficult, although a file naming convention could help resolve that problem.
  

• Project type: Large organizations with a lot of cross-departmental collaboration across numerous projects might find it easier to separate files by category first and name second. That way, everyone in the marketing and production departments working with scripts and audio files for radio spots, for instance, can find those files without having to see files related to social media ads. The downside is that finding related client projects is tricky unless you add that information into a file naming structure.
  

• Department: For large organizations with siloed departments that seldom interact, each department can have its own hierarchy. That keeps the marketing department’s files separate from the accounting department’s, for instance, but can result in confusion when departments do collaborate. Plus, it can be difficult to bring data about a single project together, although again, a good file naming structure can help.
  

We often get questions about how best to organize images. If they’re tightly related to particular projects, the easiest approach is usually to store them alongside other files in that project. For example, photos for a cookbook might live with the layout files within a folder for each chapter.

For graphically intensive fields with a very large number of images to track across multiple projects, particularly when any given image might be used in multiple contexts, consider moving to a digital asset management app that stores all your images, providing access through hierarchical categories and keywords or tags. Digital asset management apps are essentially databases for images and other media, enabling you to search and sort far more flexibly than with a simple folder hierarchy.

#3: Decide on a Consistent File Naming Convention

Although an organizational structure is important to help you find files quickly and work with related files, your file naming convention is even more important. You should be able to identify a file merely by glancing at its file name, even if it was moved outside its folder hierarchy. That’s especially true if files are shared outside your organization, where the recipient won’t see the folder hierarchy above the file. You can see this problem illustrated below: you can tell exactly what this Mailchimp.pdf file is from the folder structure, but would someone else have any way of knowing it’s a Belvedere Hotel-related invoice from 2022?

File names should be as specific and detailed as necessary for quick identification, preferably starting with a date or project name and including essential aspects of the organizational structure. Dates work well for any file that’s created on a regular basis—instead of the vague MailChimp.pdf, try 2022-09-29-Belvedere-invoice-MailChimp.pdf. Project names are better for one-offs, so instead of Chapter3.docx, use something like Second-Breakfasts-Ch03-recipes.docx. Note how both of those names integrate key aspects of organizational structure.

Three pieces of advice:

• When you name files starting with the date, use the YYYY-MM or YYYY-MM-DD format to ensure that they sort well and can’t be confused with older or newer files.
• Consistency is key. Stick to the conventions you decide to use and require that everyone else do so as well. Having one file name start with “Second-Breakfasts” and another with “2nd breakfasts” will cause confusion and annoyance.
• When separating words, use a space, a hyphen (-), or an underscore (_). Spaces are the easiest to use but should be avoided for files destined for a website. We prefer hyphens because macOS interprets two words separated by an underscore as a single word when selecting, which can be irritating while editing file names.

#4: Identify Versions Clearly

Many files go back and forth between multiple people in a collaborative workflow. Building a versioning scheme into your file naming convention is essential to ensure that everyone knows which version is the most recent and who worked on which version. It’s tempting to use a single file, with each person renaming it as necessary, but we recommend archiving each version until the completion of the project to make it easy to see who did what and to recover from any file corruption or accidental deletion of data. When using a file server or shared folder, it’s best to make it clear when someone is actually working on the file to avoid collisions. Let’s assume in these steps that you and your editor are taking turns working on a Word file.

1. Alongside the file in question, create a folder called CHECKED OUT and another called OLD.
2. Move the file you’re working on into CHECKED OUT. Name the file however you like, but end it with your initials and the number 1, as in Second-Breakfasts-Ch03-layout-rte1.docx.
3. After you make your changes, move the file back into the main folder and alert your editor that it’s available.
4. When your editor wants to work on the file, they first make a copy of it in OLD to archive a version. Then they move the working copy into CHECKED OUT and rename it with their initials, incrementing the version number, as in Second-Breakfasts-Ch03-layout-afp2.docx.
5. They edit the file, moving it back to the main folder when done and alerting you.
6. You each then repeat Steps 4 and 5 as necessary, storing an archive copy in OLD, putting the working file in CHECKED OUT, renaming it with initials and the next version number, and then putting it back in the main folder when done.
7. On the final revision, rename the file one last time, replacing the initials and version number with “final,” as in Second-Breakfasts-Ch03-layout-final.docx.

If you’re instead sending files back and forth via email, there’s no need for the CHECKED OUT folder, but you should both keep a copy of each version in OLD, just in case.

#5: Know When to Browse and When to Search

If you have a solid organizational structure, you should be able to jump right to the files you need by navigating the folder hierarchy, and if you’ve designed your structure well, you’ll browse for files most of the time. However, if a consistent file naming convention enables you to fall back on searching in certain situations:

• You need to find files across multiple folders. For instance, if you store files by client but want to see all the invoices for all clients, a search on “invoice” is more effective than looking in each client folder separately.
• There are too many files to work with fluidly. Imagine that you have an automated system that generates dated reports for multiple suppliers in a particular folder. If they’re sorted first by date and then by supplier, a search could help you filter the folder’s contents to a single supplier.
• You don’t entirely understand the organizational structure or trust that others have followed it. This scenario is most likely when you weren’t the person to set things up. Hopefully, you at least have consistent file names to look for with your searches.

Apart from these situations, if you find yourself regularly resorting to a search, that may be a hint that you should revisit the organizational structure and make sure it works the way you need.

As you can see, there are numerous approaches for organizing and naming your files, and what makes sense for one group may not for another. If you’re having trouble deciding on the best approach, feel free to ask us for suggestions.

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