Open multiple files by dragging them onto app on the Dock

One other little thing, since you asked about using the keyboard: rather than dragging to the Dock icon (which somehow is not working for you), you can open all these files at once by pressing Command-O or Command-down arrow. No need to drag or use the mouse at all. Command-A Command-O and all the files open in the designated application (even if these are differen types, eg some html files open in Safari and at the same pdf files open in Previw).

About opening files with an application other than the default, macOS has got you covered as well. The easiest is via "Open With", but you can do it from the keyboard as well, thanks to Services (or, now, "Shortcuts"/"Quick Actions" as well) and keyboard shortcuts.

I don't have Adobe software on my mac, so you may have to adjust the name of the application in case it is named differently; but the following Automator Quick Action will open all selected files with Adobe Acrobat.

1) Open Automator and select "Quick Action".

2) Add a single action, in this example I put in "Run Shell Script" but it would be easy to make an alternative using "Run AppleScript" instead. Make it like this:

3) Save it with a descriptive name, say "Open with Acrobat"

4) In System Preferences->Keyboard->Shortcuts->Services, add your keyboard shortcut of choice for this.

Now, whenever you have one or more pdf files selected, just press the shortcut you chose and they open in Acrobat.

trexaurus wrote:

The drag to open functionality is neither working on the MacOS' native app Safari

It works perfectly in Safari.

Adobe suite of Apps, i.e. Adobe Illustrator, Photoshop, InDesign, Acrobat, etc.

Adobe has its own support community at https://community.adobe.com. I recommend you inquire over there.

This was the specific reason I approached Apple Community and demonstrated the issue in the MacOS' native app so that It can be validated that the issue isn't with the 3rd party apps' implementation of Open API, especially not of Adobe.

You made the right call. We have definitively proved that there is no problem in Safari and that, if you are experiencing a problem with specific 3rd party apps' implementation of the (albeit closed) API, you will need to contact those developers for support.

• Microsoft 365 suite

• Google Chrome

• Firefox

I have these apps installed and they all work file when dragging multiple files to their icons in the Dock. I don't have any of the other ones.

• VLC

I can confirm that when I drag multiple video files onto the VLC icon in the Dock, VLC plays only a single one. Maybe this is by design. It is kind of difficult to watch multiple videos simultaneously.

Ironically enough, Apple's own Quicktime Player is able to open multiple video files simultaneously by dragging icons to the Dock. They don't play automatically though.

I'm missing the ability to navigate and work in half the time with keystrokes than it takes to move the pointer / cursor all across the screen, spending too much time (cumulatively) tracking my cursor to do activities which can be done with quick keystrokes. A functionality very quick, easy, common, stable & mature in Windows.

Use of the mouse was kind of the whole point to the Mac. You might want to reconsider your switch from Windows.

On the Mac, if you need an interface substantially different than the default, I'm afraid your only options will in System Preferences. You can make some configuration adjustments to the keyboard and the mouse/trackpad. For more significant changes, you will need to see what is available in Accessibility. Many of the Accessibility options are quite useful.

About Etrecheck, while you did hint at potentially conflicting 3rd party apps, I haven't installed any app which is less than AAA standard (so to speak).

What is this "AAA standard"? One of the problems with software on the Mac is that there is no such standard. Scam apps and junk apps are extremely common. While malware isn't very common and the macOS operating system is virtually impregnable, people are relatively easier to trick and about 10% of Mac users have malware installed.

I wrote a User Tip on How to spot fake apps, junk apps, scam apps, and abandoned apps

Etrecheck though has some fragmented reviews on Google Search but there isn't enough transparency about the app from App Store or anywhere in the internet. So I'd pass on installing Etrecheck; even more so when I hear it does a low-level scanning.

Full disclosure: I'm the author of EtreCheck. So my User Tip above is designed around what I would expect to see and how I try to present EtreCheck itself. EtreCheckPro isn't in the App Store at all. I would appreciate it if you could tell me what you find "opaque" about it. The scans it does aren't particularly low-level. The only changes EtreCheck would make to your system are removing malware, and even then you have to click the button yourself. It was that anti-malware capability that let to me discontinuing that Mac App Store version. If you have been led to believe that any software is, or should be, simple and transparent, then I'm afraid you've been grossly misinformed. It's royally messy.

trexaurus wrote:

I'm able to open one / single file by dragging it on to an app placed in the dock area. However, I'm not able to open multiple files that I have selected using this same flow (dragging those selected files onto the app).

Could anyone tell me how to go about it? OR does MacOS lack the ability to open multiple files at once?

macOS definitely has the ability to open multiple files at once. However, this is dependent on an app being able to properly implement Apple's file opening APIs. People don't realize are poorly coded many 3rd party apps are. So when they see some strange and unwelcome behaviour inside an app, they blame the macOS operating system for the bug. But Apple can't force developers to write high-quality code. It is the user's responsibility to contact the developers of these apps, report bugs, and possibly even use different apps.

Is there any way we can select files in random order without using touchpad?

What do you mean by that? One of the selling points of macOS is the easy-to-use interface. I'm sure Apple could provide more complicated user interfaces. You might be able to find 3rd party apps that provide some kind of multi-step, keyboard-based file selection interface. I suppose you could select files using regular expressions in the Terminal if you wanted the ultimate in complicated ways to select files in random order without using the touchpad.

• Is there a way to compare files while merging two folders?

OR does MacOS lack all of these basic functionalities?

You aren't describing basic functionalities. macOS will select the most recent files when merging folders. That is basic functionality. If you want something more than that, you can buy something like Kaleidoscope for $150 or Beyond Compare for a bit less.

trexaurus wrote:

• Hi,

I'm able to open one / single file by dragging it on to an app placed in the dock area. However, I'm not able to open multiple files that I have selected using this same flow (dragging those selected files onto the app).

I have no problem dragging multiple image files onto the Preview icon in the Dock and have them open. What app are you having the issue with?

Could anyone tell me how to go about it? OR does MacOS lack the ability to open multiple files at once?

Nothing to tell. You just do it and they open. Does that happen with all Apps?

Is there any way we can select files in random order without using touchpad?

You could check to see if there is something in the Accessibility system preferences to allow selecting files from the keyboard. The OS was designed around using a mouse. There has never been much ability to manipulate the GUI with only a keyboard.

Is there a way to compare files while merging two folders?

The only comparison it does when you can get it to merge is by date modified and name.

trexaurus wrote:

It's with almost all the apps that I've tried including the Apple's OWN Safari app. Also in Preview.app, sometime it opens but other times ceases to.

Please find the screen grab here: https://www.youtube.com/watch?v=FkEEN3tYojc

Perhaps you have discovered some limit in the number of simultaneously open tabs in Safari. You have at least 37 tabs open. What happens to new tabs when all existing tabs are already as small as they can get? I have 11 tabs open right how and I can drag 4 html files to the Safari icon in the Dock and they all open up in new tabs.

I just used the Windows 10 and Windows 11 and it has the file comparison feature built in without any complications or complex UI. Plus, it is more accessible as it allows navigating, selecting, and doing almost anything with keyboard without configuring anything; not requiring shelling out extra bucks.

I don't know anything about Windows. I haven't used it for many years. One thing I do know is that there are actually very few 3rd party file comparison apps available for macOS. Almost all such tools are Windows tools. Kaleidoscope is one of, if no the only, native-born macOS comparison tools. There are a handful of apps that have been ported to the, such as Beyond Compare, that I mentioned above. Even that one looks like it hasn't been touched in decades. If this kind of capability is available for free in Windows, then why are there so many different comparison tools available for Windows?

please let me know if dragging is something that can be fixed.

It isn't broken.

I don’t think there is anything to be fixed. As others have said things are working and for some reason they are not working for you. This suggests a possible software conflict. As to selecting multiple files there are plenty of ways to do it. Not sure what you feel is missing.

You may want to run Etrecheck and post its report here. Maybe you felt the need to install stuff that is causing problems that you otherwise would not have.

Etrecheck is a diagnostic utility by a very respected member of this community. It is used in these forums daily so that those trying to help have enough information about the affected users' systems. It has helped solve uncountable issues here.

On the other hand, usually the ones who post negative comments often install and swear by dreadful pieces of software that often cause the problems they are experiencing. Etrecheck is free, and has a paid version with more features. Nobody is forced to pay, and yet I have often seen people claim the contrary. There is plenty of misinformation. You are not the first to post similar, misguided concerns. And maybe you installed some "cleaning" app, believing that is safe, when it is not... I know plenty of people here with issues did, and expressed the same concerns as you.

I am curious: how would you even open documents from the keyboard to other than the default applications on windows? Let alone add your own keyboard shortcuts, etc. I do not use windows unless I have to, but as far as I can tell the automation capabilities of macOS are far and above those of windows. Automator, AppleScript, the Terminal... I am a keyboard guy, and I love that I can add keyboard shortcuts to just about anything that is on a dropdown or even contextual menu.