How to Delete All Photos from your iPhone and Dropbox Camera Uploads

Eventually, you will probably run out of storage space not only on your iPhone, but in your Dropbox account, too. If you’re like me:

  • You don’t pay for extra storage from  Apple’s iCloud or Dropbox.
  • You periodically migrate your images and videos to a hard drive or backup hard drive.

When you’re ready to bulk delete all of your images on Dropbox and your iPhone, here’s a quick guide.

The Overall Process: iCloud to Dropbox to a Hard Drive

I follow this process because:

  1. Apple and iCloud make it far too difficult to access the actual image files that you store on your phone. This is true whether you have a Mac or not.
  2. Dropbox solves the above problem pretty easily. You can access your Dropbox photo files efficiently, especially if you have Dropbox installed on your desktop.
  3. Neither Apple nor Dropbox is a long-term solution because of storage limits. So you need a permanent place to save your images.

Where Should I Permanently Store My iPhone Photos?

Before we get started with the deleting, I cannot stress enough that you need to have a dedicated space where your digital photos can live long-term. Once you delete these photos from Dropbox and your iPhone, it could be very difficult or even impossible to retrieve them.

I recommend picking a device (laptop, desktop, or external hard drive) that has at least 100GB worth of storage.

  • A basic Dropbox account offers a measly 2 GB storage space.
  • Most iPhones offer between 32 and 256 GB of space.
  • This excellent external hard drive from Toshiba — and many others — offers 3 TB (terabytes) of space, and it’s barely bigger than my iPhone. Great product.

1. How to delete photos from Dropbox’s Camera Uploads

To start this process, let’s upload any and all remaining iPhone photos and videos to your Dropbox:

  1. Open the Dropbox app on your phone.
  2. Turn WiFi on.
  3. Allow all of your iPhone’s photos and videos to upload to your Dropbox “Camera Uploads” folder.
  4. Now, on your laptop or desktop computer, drag all the files from your Dropbox “Camera Uploads” into your desired long-term storage space (your hard drive, external hard drive, or other).

2. How to bulk delete photos from your iPhone’s Camera Roll

Again, Apple makes this far too difficult for iPhone users. Here’s the trick if you have a Mac:

  1. Open the application called “Image Capture” (why this feature isn’t in the “Photos” app is beyond me).
  2. Plug your iPhone into your computer, manually with a lightning cable. All your photos should now display within Image Capture.
  3. If you are absolutely sure you have imported your photos to your safe space (your hard drive), then select all photos within Image Capture. Do this by clicking Edit > Select All, clicking Command-A, or simply use the shift trick to select multiple items.
  4. Click the ‘Delete’ icon at the bottom. It’s very hidden (ugh). It’s the circle symbol with a slash in middle, right next to the dropdown menu.

Congrats, you did it! Now you have storage space on both your iPhone and Dropbox again — at least for a couple months.

My iPhone photos are not uploading to Dropbox’s “Camera Uploads” folder

One last troubleshooting note. As the months go by, if you ever notice that your photos are no longer syncing automatically between your iPhone and Dropbox, try this:

  1. Open the iPhone Dropbox app
  2. Tap “Photos.” If this still doesn’t jumpstart the sync process to Dropbox, then keep going….
  3. Tap “Account” (or “Personal”) in the bottom navigation bar > tap on the gear wheel (upper left) > then “Sign out from Dropbox.”
  4. Sign back in.
  5. Tap “Account” (or “Personal”) in the bottom navigation bar > tap on the gear wheel (upper left) > tap “Camera Uploads” > make sure that and “Upload Videos” are toggled on.


Stop Creating the OneDrive ‘Attachments’ Folder

When you open your Microsoft OneDrive folder, have you ever noticed a folder called “Attachments” that you didn’t create and you don’t want? The folder is almost always empty, it’s randomly created by Microsoft, and it will continually reappear even after you delete it. Here’s how to stop the folder from appearing.

Issue at a Glance 
DiagnosedMarch 2017
SolvedMay 2017
SystemMac OS 10.12
ApplicationsOneDrive, Terminal

Open the Terminal utility to hide the OneDrive ‘Attachments’ folder forever

From your Mac desktop or laptop:

  1. Open your “Applications” folder.
  2. Open the “Utilities” folder.
  3. Double-click Terminal to launch it.


Terminal allows users to write sophisticated code to do complex tasks on their Macs. It is important to be careful when using this utility, but please note: I am not a developer, and I know very little about Terminal. All you have to do to hide the dreaded One Drive “Attachments” folder is to write this within Terminal:

chflags hidden [*enter the unique path of YOUR folder here*]

For the “[*enter the unique path of YOUR folder here*]” part indicated above, I recommend you literally drag the offending OneDrive “Attachments” folder into the Terminal app. Your code will then look similar to this:

chflags hidden /Users/YourName/OneDrive\ -\ FolderName/Attachments

Now, hit return. You’re done! The “Attachments” folder will be hidden from view.

Here is what my Terminal app looked like when I was done with this one-line solution:


If you want to make the now-hidden folder visible again, you’ll need to enter some additional code in Terminal. Wilson Mar wrote this helpful piece and quips, “Terminal is your friend, who only speaks a foreign language.”

Why Automator won’t disable the ‘Attachments’ folder from being auto-created

I tried for weeks to use the Mac application Automator to hide this Microsoft-made monster. Similar to Terminal, Automator is a complex tool mainly for developers and engineers. In my opinion — I’m not an engineer, just a Mac enthusiast of 20+ years — Automator is a near-worthless application, because it doesn’t automate anything.

Automator will run workflows that you create, but you must manually start them. They won’t simply run in the background continuously.

To hide the One Drive “Attachments” folder permanently, my initial vision was to create a new workflow (or folder action? I could never tell which was appropriate because it’s incredibly unclear) within Automator to automatically hide the folder every time it was created.

I tried nearly every permutation possible within Automator, usually something like this:


But the wretched ‘Attachments’ folder kept reappearing, every day, for weeks. It would automatically re-create itself every 6-12 hours. I succeeded once in hiding the OneDrive folder using Automator — however, Automator had also moved all of my other OneDrive folders into the trash. I averted the crisis, but I was done with Automator.

Why adjusting your Microsoft Office 365 webmail preferences won’t work either

If you do some online research surrounding this pariah of a folder, you’ll notice that many people associate this bug with Microsoft’s e-mail program, Outlook. If you send an attachment in an e-mail, that may trigger this folder to be created. In some accounts, the auto-created folder is called “E-mail attachments” while for others, the folder is simply called, “Attachments.”

My contention is that this issue appears to be connected to OneDrive for Business. Despite what you may read on the discussion boards, the “Attachments” folder will not respond to the presumed common cure for this plague:

  1. Sign into Outlook webmail
  2. Click Settings > Mail > Attachment options > Attachment preferences
  3. Select “Always attach them as copies”

This method may work for an “E-mail Attachments” issue, but not for the folder simply named “Attachments” in your OneDrive.

Why won’t Microsoft fix the problem?

Because they’re Microsoft? I have long loathed Microsoft and their cold, clunky products. While their applications have certainly improved over the years, they still:

  • do too much thinking (and doing) for the user
  • usually offer limited customization options, from Word to Powerpoint to OneDrive
  • occasionally offer customization, but it’s too convoluted

The secondary problem here is one that plagues all tech companies. The aforementioned online discussion boards alert companies like Microsoft to bugs for months — and often years — before anything is done.

I recently asked OneDrive via Twitter to fix this inane folder issue, and they were so dense they referred to it as a “feature.”

Should I Buy the Expedia Flight Protection Plan?

When booking a trip on (or its subsidiaries Orbitz and Travelocity), you will be pushed to purchase a “flight protection plan” during checkout.

The website now makes a concerted effort to blatantly scare you into spending $19 on travel protection. Here’s why you shouldn’t do it.

Expedia Travel Insurance will Only Refund You in Extraordinary Circumstances

You will only get a refund for your online booking under very specific — and very unlikely — circumstances, including:

  • death in the family
  • extreme illness
  • natural disaster that severely damages your home

A few other scenarios are listed in the dreaded terms and conditions, which admittedly I did not read before making my mistake of buying “trip protection.”

Expedia logo

Do Not Let Expedia’s Booking Language Intimidate You

At the core of this issue is a lack of respect for the user, the traveler. goes to great lengths to fool you into buying a $19 flight protection plan. They do this through not-so-subtle language and design:

Expedia protect your flight recommended

  1. Upon entering checkout, Expedia tells you that protecting your flight is “recommended.” Recommended for whom? And by whom? It doesn’t say.
  2. Then, in foreboding red letters, Expedia warns, “Avoid change fees. Protect your trip.” Protect my trip from what? It doesn’t say.
  3. There’s a deceptive link that reads, “3 reasons you might need travel protection.” Might is a curious word. More on this later.
  4. The website also puts words in the customer’s mouth if you say “no” to trip insurance: “I’m willing to risk my trip.” Sheesh.

If you do click “No” and try to opt out of the travel protection plan, displays a warning message: “Your trip is not protected.” And it prompts you to “reconsider.”

Expedia your trip is not protected warning

All of this is manipulation and intimidation. Expedia is not telling the whole story.

Before You Buy Expedia Insurance, Read the Terms and Conditions

At this point, you might be thinking that you want to be a more educated consumer about Expedia’s flight protection plan option. You might click on the blue link: “3 reasons you might need travel protection.”

Expedia 3 reasons you might need travel protection

These aren’t reasons you “might” need travel insurance. They’re basically the only three reasons you would need it, because if none of these three scenarios happen, you can kiss your refund goodbye.

And now we come to the terms and conditions — that tiny little blue link — “View terms, conditions, and plan sponsors” — which, of course, doesn’t even appear to the user, unless you actually click on “3 reasons you might need travel protection.”

The terms and conditions (3,500 words in all), to be fair, do explain the scenarios in which the travel protection plan will actually protect you. So yes, I should have read the fine print. But did I want to spend even more time researching T&Cs after having spent over an hour researching flights, hotels, and more? Not really.

To add further confusion if you do want to perform exhaustive research on travel insurance, Expedia offers at least four protection plans with nearly the same name:

  • Expedia Package Protection Plan
  • Expedia Vacation Waiver
  • Expedia Cancellation Plan
  • Expedia Total Protection Plan

Happy T&Cs reading!

Why I Opted for Expedia Flight Protection — and Regretted It

I was slated to go to a business conference for one client, and I had another client who was possibly going to be in that same city that same week. Thinking that I might need to adjust my flights pending my client’s plans, I bought Expedia’s $19 flight “protection” plan.

A couple weeks after I booked the flights, the work conference was rescheduled, so I needed to cancel my flights altogether. Time for my “flight protection insurance” to kick in, right?

Nope. This is where I learned that I would receive no refund, and almost no credits. My trip protection only would have protected me if I had had a death or illness in the family, or the aforementioned, very unlikely reasons.

I called Expedia to complain, but to no avail. Policy is policy, they said. I told them their website was deliberately misleading.

In the end, my $256 plane ticket turned into:

  • $200 down the drain due to a “reissue fee” from United Airlines (another gripe altogether)
  • $56 in credits to use toward a future reservation

To further annoy me, I will have to call Expedia to use my $56 United credit — I can’t simply apply it online. Another poor user experience.

Is Expedia’s Flight Protection Plan Worth it?

In the vast majority of circumstances, buying Expedia travel insurance is not worth it. If you do the math, the only way it’s worth it is if once every 10 trips, one of following events happens:

  • You get extremely sick.
  • You have a death in the family.
  • An act of god destroys your house.

Here’s the math. If you:

  • purchased trip protection ($19) on each of your next 10 trips, you’d spend $190. Guaranteed.
  • needed to change or cancel a flight (highly unlikely) from United, American, or Delta, you’d pay $200.

Need more advice? Here’s how you can try to avoid change fees or reissue fees moving forward: