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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?
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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.