Hey my current setup is internal drive windows and external drive ubuntu(Personal) which I connect through usb. I was wondering if anyone knows if connect a new ssd(work) and install ubuntu on to it. Would I be able to connect my personal one to use that image then disconnect personal and connect and use my work one so switch between them freely like that? At any given time there would be only one external drive connected.
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Yes, it is possible. Just like you installed the external drive Ubuntu (Personal), you can install Ubuntu into a new SSD (work). This works if the SSD is connected via USB or eSATA. Maybe the following link will help, Boot Ubuntu from external drive – sudodus May 24 '18 at 14:29
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It's possible to boot with multiple OS ("dual" boot is not actually restricted to two) from an external drive, but if by "switching between them freely" you mean swapping them on the fly, then no: you'd need to reboot the laptop anyway to boot into a different OS (or "hibernate"; as long as the RAM is not engaged). This would still be the case even if both operating systems were on the same disk.

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@AryoAdhi, I never thought of that, but it makes sense. You can still, technically, mount a Win partition, but Linux won't write to it to prevent problems. This might be beyond what the OP asked, but with a dual-boot system, I would probably use a separate data-only partition, anyway, so that my files were easily accessibly from every OS. – Ratler May 25 '18 at 08:21
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Still, if the OP wanted to have a "universal partition", disabling fast boot is a necessity. – Aryo Adhi May 25 '18 at 09:00