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If there's more than one update for a particular program available, do I download and install both, in numerical order? Or do I just download and install the most recent, i.e., have the highest version number?
you do NOT need to update any adobe programs (or the cc desktop app itself) sequentially. each update installs the entire program and does not augment a previous install.
ie, the only reason to install a non-current version is that you want to use it (perhaps in addition to the current version). you can have multiple versions of each adobe program on one computer.