It's not always illegal. In the U.S. it's neither illegal nor legal (it's an untested law.) The Library of Congress issued an exemption to the DMCA allowing people to download archival copies of vintage software when they meet certain conditions. Unfortunately he lives in Canada, so this doesn't really apply to him (every country has different laws, of course), but if he were in the U.S., his Adobe software falls squarely under the DMCA exemption.