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Probably when they were on the verge of bankruptcy in 1996/97. edit: link: https://www.news.com.au/technology/gadgets/the-forgotten-microsoft-deal-that-saved-a

• Jtsummers 6y ago
  That may be what they're referring to, but Apple wasn't using Objective-C at that point, NeXT was.
• kazinator 6y ago
  In 1996/1997, the Macintosh was still, for most end-users, the only viable alternative to an IBM PC derivative, and one with market share. The old Mac OS didn't use Objective-C-based frameworks. Objective C was used on the NeXT workstations. Objective C became popular because it was part of the tech stack brought back into Apple by Jobs.