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You'll need to create a debug log (right-click on Preferences, then select "Restart in debug mode", then import an ACSM, then exit Calibre). Hopefully somewhere in there will be a useful error message.
Most common issues is that the ACSM has already been opened with another AdobeID, or the ACSM is expired (they need to be used shortly after they've been downloaded, usually).
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