Unlocking Document Accessibility Across Apple Devices

Ever felt like your important business files are playing hide and seek across your Apple devices? Today, we’re unveiling the secret to having your crucial documents at your fingertips, no matter which Apple gadget you’re using.

I’ll unpack all of this after the intro.

Welcome to the Macpreneur Podcast

Hello, hello, and welcome to episode 90 of the Macpreneur podcast. Whether it’s your first time or you’re a longtime listener, I appreciate that you’ve carved out some time in your busy solopreneur schedule.

I’ve created Macpreneur to help as many solopreneurs as possible save time and money running their business on their Mac.

Boosting Your Mac Efficiency: Tips and Tricks

In order to help you be more efficient on your Mac, I need to know how well you’re currently dealing with the 3 killers of Mac productivity, namely: unnecessary clicks, repetitive typing, and file clutter. 

For that, just visit macpreneur.com/tips and answer a few questions, which will take you less than two minutes.

After submitting your answers, you’ll receive personalized time-saving tips based on your results. Once again, visit macpreneur.com/tips and start boosting your Mac efficiency today.

Okay, so as a successful solopreneur, you are likely using more than one Apple device in your daily operations.

This episode is the last one of a three-part series, where in episode 88, I dove deep into iCloud synchronization, and in episode 89, I covered different strategies to quickly install our most used applications.

If you missed those episodes, either make yourself a mental post-it note or visit macpreneur.com/season4, where you will be able to find them.

And so today, we’ll explore how to make sure that we can access business-critical documents across all our Apple devices.

Navigating iCloud Drive: Advantages and Disadvantages

Before talking about synchronizing documents from third-party cloud providers, I would like to briefly cover iCloud Drive, especially its main advantages and disadvantages. The first advantage is that among the big four—Apple, Google, Microsoft, and Dropbox—iCloud Drive is the only cloud storage provider that offers end-to-end encryption without negative side effects when dealing with documents.

It still requires you to activate advanced data protection, which means configuring a recovery contact or recovery key and making sure that all your devices run at least macOS Ventura 13.1 or iOS and iPadOS 16.2.

Now, I said without negative side effects because Google Drive technically can also accommodate end-to-end encryption, but you will face a lot of restrictions. For example, you won’t be able to collaborate on Google documents in real-time. And if you install the Google Docs, Google Sheets, Google Slides mobile applications, well, bad luck, you will not be able to edit documents that are encrypted end-to-end, which is not the case with iCloud Drive. This is why iCloud Drive has that as a big advantage: both security and the ability to edit and manage documents.

The second advantage of iCloud Drive is that it’s deeply integrated into the Mac operating system. So, in Finder, for instance, if you apply color tags or name tags, those will get synchronized across all your Apple devices.

In Finder, if you right-click on a file or a folder stored in iCloud Drive, you will see a share option.

If you click on that, then it’s super easy to choose whether you want to send a copy or if you want to collaborate with others. You’ll even have direct access to the recently contacted people in messages.

You can quickly select the mail app to send the link without even needing to launch Mail in the first place. However, there is an important thing to keep in mind about iCloud Drive. When you share a file or a folder, the recipient needs to have an iCloud account. It’s not a big deal if you collaborate with other people who have Apple devices and most likely will also have an Apple account, but as soon as you share files with someone outside of the Apple ecosystem, they will need to create an Apple account just for collaborating with you on those iCloud Drive documents.

On top of that, they will only see or edit the documents from the iCloud.com website.

And finally, the biggest drawback of iCloud Drive, in my opinion, is how little control we have over choosing which files and folders can be accessible offline.

Now, unlike OneDrive, Google Drive, and Dropbox, with iCloud Drive, it’s an all-or-nothing situation.

If you go to System Settings or System Preferences, and then open your Apple account, you go to iCloud, you will see that there is an “Optimize Mac Storage” option. If you leave that option off, it means that all your iCloud Drive files will be stored locally on your Mac.

But as soon as you turn on “Optimize Mac Storage,” you give away all control to macOS.

So, yes, you can force the temporary download of a file or a folder, but there is no guarantee that it will always be locally on your Mac. If at one point the internal storage space gets too low, macOS will remove all the necessary local versions based on criteria that Apple has decided on our behalf.

And so, all this combined explains why I only use iCloud Drive to easily synchronize Keynote, Pages, and Numbers documents, as well as data that I want to access from within certain applications.

Mastering Third-Party Cloud Synchronization on Mac

Okay, let’s delve into synchronizing documents stored with third-party cloud providers. I’ll start with the Mac. The first step is to install the Cloud Synchronization Companion app. This could be the Dropbox app, OneDrive, Google Drive, or the Synology Drive if you have a Synology NAS.

It’s important to carefully configure whether all files get synchronized locally on your Mac or are available on demand when installing third-party synchronization companion apps. Local synchronization means all your documents are downloaded to your Mac, allowing you to access and edit them even without an internet connection.

This seems like a great idea unless your Mac’s internal storage capacity is less than what you store in the cloud, which is particularly true for MacBooks with 128 or 256 gigabytes of internal storage. If you have more data in the cloud than your Mac can accommodate locally, the only solution is to opt for on-demand access. You can still see all the files available from your cloud storage provider, but they don’t occupy any space on your Mac unless you double-click on one to start working with it. It will download the file and then upload the modified version to the cloud when you’re finished.

Unlike iCloud Drive, you can choose which files and folders can be accessible offline and stored permanently on the Mac’s internal storage. Remember that cloud documents are not backed up by Time Machine. If you only have one Mac, you will need to find another solution to have a backup copy of those documents in the cloud. This is a topic that I will cover in Season 5, and those episodes will be available at macpreneur.com/season5. If you’re listening in the future and are interested in online and data security, just visit macpreneur.com/season5.

The second thing to pay attention to, especially when installing Dropbox on your Mac, is the potential conflict with the synchronization of your desktop and documents folder. Since both iCloud and Dropbox can synchronize these locations, it can create problems if you’re not careful during the Dropbox setup process. If you’ve already activated this feature for iCloud and now want to supersede it with Dropbox, it could cause future issues. I’ve had one client who experienced this, and it was challenging to resolve.

The third thing to watch out for, especially when moving files and folders into your preferred cloud storage, is incompatible characters in file and folder names. OneDrive is particularly strict, as it doesn’t accept double quotes, asterisks, colons, less than, greater than symbols, question marks, backslashes, forward slashes, or the vertical bar, sometimes called the pipe symbol. It essentially rejects all characters that are illegal in Microsoft Windows, penalizing Mac users. Additionally, a file or folder name in OneDrive cannot start or end with a space. If you have files or folders on your Mac named in such a way and want to move them to the OneDrive folder, they will be copied but OneDrive will indicate that it cannot synchronize them with the cloud. Therefore, these files and folders will only be available on your Mac and not in the cloud or on other devices with the OneDrive app installed.

Moreover, the file path, which includes the entire folder structure followed by the file name, cannot exceed 400 characters. Some of my clients prefer Outlook and want all their documents in Microsoft 365. I’ve assisted a few in migrating, always dealing with the same issues, teaching them proper naming conventions for folders and files, and ensuring they notice the red cross on the OneDrive icon in the menu bar that signals synchronization issues.

On the other hand, Google Drive has no such limitations, except those imposed by macOS. In Finder, for example, the only character not accepted is the colon in a file or folder name.

Optimizing Mobile Access to Cloud Documents

Okay, let’s switch gears and go to mobile device access.

If you want to access your documents on your iPhone or iPad, the best option is to install a third-party cloud storage app on your device. This could be the mobile version of OneDrive, Dropbox, or Google Drive. After downloading it from the App Store, you just open it and sign into your cloud account.

First tip: Like with the desktop equivalent, it is possible to request that a particular folder or file be downloaded to the device so that you can access them even without an internet connection. For that, you usually need to tap on the three dots to the right of the folder or filename, and then you will see an option that says something like “make available offline.”

Tip number two: In the Mail app, if you want to be able to attach a file from a third-party cloud storage provider, then you will need to ensure that they appear in the native Files app on your iPhone or iPad. Normally, third-party cloud storage access is activated as soon as you install the mobile application. But if they don’t appear in the Files app, tap on the three dots in the top right corner, then tap “Edit,” and there you will be able to toggle on access to the third-party cloud storage app that you have installed, for instance, Dropbox, OneDrive, and so on. After that, you just tap on “Done” in the top right corner, and that’s it.

Okay. Back to attaching a file in a new email message using the Mail app. So, you long press in the body of the email, and you’ll see a pop-up with a few options like “Paste” and “Select.” There, you just tap on the symbol that looks like a greater than character as many times as needed until you see an “Attach File” button. You tap on it, and the Files app interface will appear. And so, if needed, you tap on the “Browse” button in the bottom right corner, and then you will see all your third-party cloud providers. You tap on the one you need to navigate to, and you select the file that you want to attach, and it will then be attached to the email.

Tip number three: To edit files on the go, it’s best to install apps that can natively deal with them. So, if you use OneDrive, then the best option is to install the Microsoft 365 application, which can edit and create Word documents, Excel spreadsheets, and PowerPoint files. And if you use Dropbox, chances are that you’re dealing with Microsoft Office documents as well, so installing the Microsoft 365 app is also recommended.

If you’re a Google Workspace customer, then you’ll need to install the mobile versions of Google Sheets, Google Docs, and Google Slides.

In both cases, whether Microsoft 365 or Google Workspace, the mobile applications are much less feature-rich than either the desktop or the web equivalent, so you will be able to do some light editing, but not much more than that.

Leveraging iCloud for App Data Synchronization

Before the recap, there’s one more thing I’d like to mention.

So, back in episode 88, I said that iCloud cannot sync application data. Well, this was partially true. The reality is that it depends on whether the app developer incorporated iCloud Drive synchronization or not.

So, services that are cross-platform, meaning available outside of the Apple ecosystem, like on Windows computers and Android smartphones, tend to synchronize stuff through their own servers. So, the only thing that a developer will use iCloud for is to back up app data.

However, when a developer decides to focus on the Apple platform, meaning developing apps that will only run on Mac, iPhone, and iPad, more often than not, they will offer the ability to synchronize data via iCloud Drive.

This means that iCloud Drive must be enabled at the device level, but it does not necessarily mean that you will be able to see the files in iCloud Drive.

For example, I’m using Ulysses for every blog post on the Macpreneur website. And yes, I’m able to synchronize all those posts and an entire folder structure between my iMac, my MacBook Pro, iPhone, iPad, connected to my EasyTECH iCloud account, but when visiting iCloud Drive, there is no Ulysses folder because the developer decided to use iCloud only as a synchronization engine. And that means that all those files and the folder structure are hidden somewhere, but I can’t see them in Finder.

On the flip side, I’m using another app called JustPressRecord, which allows quickly recording audio from any Apple device, and then getting this audio automatically transcribed.

Well, it’s possible to configure JustPressRecord to store the recordings in a dedicated folder accessible from iCloud Drive. The process is usually I will record something on my Apple Watch. This will get saved into iCloud Drive, and so to access those recordings from my Mac, I just open Finder and go to iCloud Drive and visit the right folder.

Or on my iPhone or iPad, I open the Files app, and again, the same thing, I can see and open the recorded audio files.

Recap and Next Steps for Solopreneurs

So to recap, we’ve explored different ways to maximize your efficiency as a solopreneur when it comes to synchronizing business-critical documents via the cloud.

First, I’ve briefly explored the pros and cons of iCloud Drive and why it’s not necessarily the best option for solopreneurs, especially when collaborating with people outside of the Apple ecosystem.

Second, we’ve looked at different ways to manage third-party cloud documents on our Macs.

And finally, best practices and tips for efficiently accessing and editing those documents on iPhones and iPads.

If you found this episode useful, please share it with a fellow solopreneur and tag me on Instagram; my handle is @macpreneurfm.

So that’s it for today.

The format of the next episode will be slightly different because I’ve asked a bunch of solopreneur friends of mine to share their favorite tool when it comes to the operations side of their businesses.

And more specifically, what helps them best serve their clients. So make sure to subscribe or follow this podcast to get it automatically next week.

If you have a question about running a solopreneur business on a Mac, I’d be happy to answer it in an upcoming episode of the Macpreneur podcast. For that, just visit macpreneur.com/question or click on the link in the show notes. 

Tell me who you are and what your business is about, then ask your question either in text format or by recording a short video.

Once again, visit macpreneur.com/question to get my answer in a future episode of the Macpreneur podcast.

And until next time, I’m Damien Schreurs, wishing you a great day.

Thank you for listening to the Macpreneur Podcast. If you’ve enjoyed the show, please leave a review and share it with a friend right now.