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I wonder how I can open two documents at once in Google Drive. Selecting two documents then hitting on ENTER didn't do the trick (no document gets open)

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Quick answer: More browser tabs.

In general, it depends. It hinges on distinctions that are subtle to some people (the UI makes them look similar). To be honest, it's a usability design problem that all this is so subtle and complicated.

  1. When using Google Drive in the browser, if you select one of its built-in file types (Google Docs, Sheets, Slides, ...) then press Enter, it will open the web-based editor in a new browser tab. This also works with apps like MindMup that install into Google Drive.
    • To open another such document at the same time, just switch back to the Google Drive tab, select another document, and press Enter or double-click it.
  2. When using Google Drive in the browser, if you select a PDF, photo, plain text file, audio file, Word doc, etc. then press Enter, it will open a read-only preview of that file overlaying the Google Drive file list in the same browser tab.
    • To open another such preview, just open another browser tab, navigate to the Google Drive folder, select your file, and press Enter.
  3. When using Google Drive in the browser, if you select a document type that it doesn't handle, the only thing Drive can do with it is download it to the local disk on your computer or Chromebook. Also you can choose to download a PDF or similar file that Drive can preview.
    • After downloading a file, you can open it in any suitable program you have available. For a PDF, that could be Adobe Reader, Apple's Preview program, the quick-look feature within the Macintosh Finder, or others. These will each offer different features.
    • To open multiple such files, just download them all, then open them into separate windows/applications.
    • Caution: After downloading a PDF file in Chrome, clicking the "downloaded file" button at the button of the window will open the PDF file in a new browser tab, even though you took pains to download the file. You probably downloaded a PDF to open it in Apple Preview or Adobe Reader, and that's not what happened. To fix this, close the browser tab, switch from the browser to the desktop, then open the downloaded file there.
  4. When using Google Drive synchronized to a folder on your computer's desktop, you can open multiple files into separate windows/applications. Here you're using your local desktop software to open the files and optionally to choose the apps.
  5. (Yet more cases!) When you're in the browser and see a link to a PDF file (this might also work for a recorded audio file), clicking, or Command-clicking, or Control-clicking, or right-clicking the link might (A) open the file in the browser tab, (B) open it in a new browser tab, (C) download it to your local disk. The right-click menu gives you better control over these alternatives.

It does matter whether you open a PDF file in Chrome vs. Preview vs. Reader if (for instance) you want to copy some of its contents or fill in a form.

  • BTW it's also fine to open Gmail in two or more tabs. Very handy. The only hitch is that you have to reload a tab to get any edits to Contacts. – Jerry101 Feb 14 '16 at 4:56
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    This answer is about how to deal with a missing feature, right? – Rubén Feb 24 '16 at 18:06
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    @Rubén I think of it as dealing with a usability problem rather than a missing feature. The UI is too complicated, partly because it tries to do us a favor, or rather, different favors in different cases. – Jerry101 Feb 25 '16 at 20:47
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I don't know about 2 files, but Alice Keeler has a Chrome extension that allows you to open the first 20 files all at once: Drive 20

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