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I'm having a similar problem to this, everything worked fine until about a week or two ago. While opening a file (ai, eps etc.) by double clicking and then opening another file, the second one won't open.
However, unlike the person from the previous thread, when I launch Illustrator first (without opening any file) it will work fine (multiple files open as expected) - so that's my workaround for now.
• Windows 10 Pro 64 bit, ver 1703, OS build 15063.540
• Illustrator ver 21.1.0
• Recent Windows updates include: KB4034674, KB4034662, KB4025376, KB4025342
• Restarts don't help
• Adobe Cloud is running fine
Hi Mike and Uzny,
That post was regarding copy paste issue, not opening multiple files at one time.
Here is the thread: Re: Illustrator CC 2017 21.1.0 crashes every time I copy any object
However, the second/multiple file issue on windows is also a known error which has happened with multiple users and has been fixed in upcoming release.
Please check this thread: Double Clicking Illustrator Files Does Nothing (seemingly)
Try the following steps and share your results.
Please check which graphic card
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srishtib8795206​from Adobe had replied to a similar post about a know issue on this, and to roll back you system. I mentioned her as she is likely more up to date on windows than myself, and may be able to tell you the exact versions and if 1703 is a problem.
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Hi Mike and Uzny,
That post was regarding copy paste issue, not opening multiple files at one time.
Here is the thread: Re: Illustrator CC 2017 21.1.0 crashes every time I copy any object
However, the second/multiple file issue on windows is also a known error which has happened with multiple users and has been fixed in upcoming release.
Please check this thread: Double Clicking Illustrator Files Does Nothing (seemingly)
Try the following steps and share your results.
Please check which graphic card you are using, it has been reported with NVidia Graphic cards on Windows OS.
Please turn off GPU Performance from Edit > Preferences > uncheck Animated Zoom and GPU performance.

It Should work fine after that but that's a temporary solution and it will be fixed in our upcoming release.
Please do share your findings and observation on the discussion.
Regards
Srishti
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Hi Srishti,
That did the trick, thank you.
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