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Field Note: Can Apple Intelligence Pass the File Cabinet Test? · AI Tools for Practicing Lawyers

• 0:03
  SPEAKER_01: Welcome to AI Tools for Practicing Lawyers.
• 0:07
  SPEAKER_01: Practical, no-nonsense guidance to help attorneys put AI power to work in their practice right now.
• 0:15
  SPEAKER_00: Welcome back.
• 0:17
  SPEAKER_00: Apple held its annual Worldwide Developers Conference today, and for years now, each successive keynote has become a little less interesting to me as an Apple fanboy dating back to the 1980s.
• 0:30
  SPEAKER_00: But this year was different.
• 0:31
  SPEAKER_00: The focus wasn't on a faster processor or a prettier interface.
• 0:35
  SPEAKER_00: The focus was on AI.
• 0:37
  SPEAKER_00: More specifically, the focus was on how Apple intelligence is going to be woven throughout the Apple ecosystem.
• 0:46
  SPEAKER_00: Apple appears finally to be getting serious about AI.
• 0:52
  SPEAKER_00: And, you know, I recently had a chat with Gemini where I asked, Apple's famous for letting others break in the market and break in the tools before Apple comes in and makes everything much better and makes a lot more money doing it.
• 1:12
  SPEAKER_00: Is Apple going to do the same thing with Apple Intelligence?
• 1:15
  SPEAKER_00: And this was our really first glimpse at seeing if it could.
• 1:19
  SPEAKER_00: Before I go any further, I want to make something really clear.
• 1:22
  SPEAKER_00: This is not a review.
• 1:24
  SPEAKER_00: I haven't used any of these features.
• 1:27
  SPEAKER_00: Nobody has, because Apple hasn't shipped this yet.
• 1:31
  SPEAKER_00: There's going to be a beta version available for developers.
• 1:35
  SPEAKER_00: There's going to be a public beta available in July, but it's not going to ship to the general public until the fall.
• 1:44
  SPEAKER_00: So this is not a workflow options episode.
• 1:48
  SPEAKER_00: These are simply my observations after looking at today's keynote.
• 1:53
  SPEAKER_00: And my biggest takeaway may surprise you.
• 1:56
  SPEAKER_00: I don't think Apple is trying to build the smartest AI.
• 2:00
  SPEAKER_00: In fact, I don't think that's even possible.
• 2:03
  SPEAKER_00: Apple will be using Gemini for some, if not all, of the intelligence behind these features.
• 2:13
  SPEAKER_00: And even if Apple develops increasingly capable models of its own, I don't think the story here is about who has the smartest model.
• 2:22
  SPEAKER_00: The story is about accessibility.
• 2:26
  SPEAKER_00: You know, there's an old Steve Jobs line that the best camera is the one you have with you when you want to take a great photo.
• 2:35
  SPEAKER_00: And maybe the same thing is true of AI, that the best AI isn't necessarily the smartest AI.
• 2:42
  SPEAKER_00: The best AI is the one you can easily and seamlessly access when you need it, the one that's already there.
• 2:50
  SPEAKER_00: The one that requires the fewest clicks.
• 2:54
  SPEAKER_00: So this appears to be Apple's strategy.
• 2:58
  SPEAKER_00: The announcement that I think will fly completely under the radar for most lawyers is shortcuts.
• 3:06
  SPEAKER_00: If you've never used shortcuts, you're not alone.
• 3:09
  SPEAKER_00: I've owned Apple devices for years and barely touched it.
• 3:13
  SPEAKER_00: In fact, my daughter, who I watched the keynote with today, has never used it at all.
• 3:18
  SPEAKER_00: And it's not surprising.
• 3:20
  SPEAKER_00: The current version of shortcuts is a little dense and hard to understand.
• 3:27
  SPEAKER_00: And while shortcuts has been one of the most powerful applications, it's also been one of the least used.
• 3:34
  SPEAKER_00: Because it requires users to think a little bit like programmers.
• 3:38
  SPEAKER_00: You had to understand actions and variables and conditions and workflow logic.
• 3:43
  SPEAKER_00: For many people, that was enough to make them walk away.
• 3:47
  SPEAKER_00: But Apple announced that shortcuts will now accept natural language instructions.
• 3:52
  SPEAKER_00: And if that works the way Apple demonstrated it, I think it could be one of the most important announcements of the entire keynote.
• 4:00
  SPEAKER_00: Not because it's flashy and not because it's exciting, but because workflows are where the real value lives.
• 4:07
  SPEAKER_00: If you've listened to this podcast for any length of time, you've heard me say that prompting is useful, but workflows are transformational.
• 4:16
  SPEAKER_00: Imagine telling your phone, when I receive a PDF from a client, save it to my bankruptcy folder, rename it with today's date, and remind me tomorrow morning to review it.
• 4:28
  SPEAKER_00: Or when I finish recording a podcast episode, save the transcript, create a task list, and remind me to create clips.
• 4:37
  SPEAKER_00: Frankly, which is the workflow that I developed with Claude that I'm going to be talking about at greater length in a subsequent episode.
• 4:46
  SPEAKER_00: Or when I receive a court notice by email, save it, create a calendar entry, and notify my assistant.
• 4:53
  SPEAKER_00: If lawyers can build workflows simply by describing them in plain English, that could dramatically lower the barrier to automation.
• 5:02
  SPEAKER_00: And that's something I'm very interested in testing when I get the chance.
• 5:07
  SPEAKER_00: The second thing that caught my attention today is something most people probably won't even notice, and that's iCloud.
• 5:14
  SPEAKER_00: For years, iCloud has been the neglected stepchild of the file storage world.
• 5:20
  SPEAKER_00: Claude has connectors for Google Drive, ChatGPT has connectors for Google Drive, Gemini obviously integrates with Google Drive.
• 5:29
  SPEAKER_00: Microsoft has been aggressively integrating AI into OneDrive and the Microsoft ecosystem.
• 5:36
  SPEAKER_00: But iCloud has largely been absent from the AI conversation.
• 5:40
  SPEAKER_00: And that raises an interesting question.
• 5:43
  SPEAKER_00: Can Apple Intelligence finally unlock the value that's already sitting inside iCloud and Finder?
• 5:52
  SPEAKER_00: Regular listeners know exactly where I'm going with this.
• 5:56
  SPEAKER_00: Can it pass the file cabinet test?
• 5:59
  SPEAKER_00: Can it find the pleading I vaguely remember reviewing last week?
• 6:03
  SPEAKER_00: Can it locate the PDF buried three folders deep inside the Finder?
• 6:08
  SPEAKER_00: Can it retrieve information from emails, attachments, notes, and documents without forcing me to manually hunt for them?
• 6:17
  SPEAKER_00: Because if it can do that, lawyers, especially Mac using lawyers, may find it incredibly useful.
• 6:25
  SPEAKER_00: Not because it's smarter than Claude, not because it's smarter than ChatGPT, but because it removes friction, and friction is what kills productivity.
• 6:36
  SPEAKER_00: Apple also spent a great deal of time discussing privacy.
• 6:40
  SPEAKER_00: Much of Apple intelligence operates directly on the device.
• 6:44
  SPEAKER_00: And when cloud resources are needed, Apple repeatedly emphasized its private cloud compute architecture.
• 6:51
  SPEAKER_00: Now let's be clear: privacy is not privilege.
• 6:55
  SPEAKER_00: A privacy-focused architecture is not an ethics opinion.
• 6:59
  SPEAKER_00: And none of this relieves lawyers of their obligation to understand how confidential information is being handled.
• 7:06
  SPEAKER_00: But it does suggest that Apple understands that trust will be a critical factor in AI adoption.
• 7:14
  SPEAKER_00: So what's my bottom line?
• 7:16
  SPEAKER_00: Well, there is no bottom line yet because I haven't even looked at the product.
• 7:20
  SPEAKER_00: But the biggest AI story from WWDC 2026 is not that Apple built the smartest AI, it's that Apple appears to be trying to make AI invisible.
• 7:33
  SPEAKER_00: Not a separate website, not a separate chatbot, although there is a standalone Siri, and forgive us for using the Siri nomenclature because Siri took a lot of hot water over the years.
• 7:50
  SPEAKER_00: Apple is sticking with Siri, and they're trying to weave it directly into the operating system as an AI tool.
• 8:01
  SPEAKER_00: So hopefully it will be something that quietly helps you find information and organize it and act on it.
• 8:09
  SPEAKER_00: For lawyers, that could mean less time hunting for files or entering data or managing digital clutter and more time doing actual legal work.
• 8:21
  SPEAKER_00: So can Apple Intelligence pass the file cabinet test?
• 8:27
  SPEAKER_00: Can I do an episode of folder mania with Apple Intelligence?
• 8:32
  SPEAKER_00: Can it find the information I need when I need it most?
• 8:36
  SPEAKER_00: Can natural language shortcuts finally make workflow automation accessible to ordinary lawyers?
• 8:44
  SPEAKER_00: If the answers to those questions is yes, then Apple's most important AI announcement may not have been Siri at all.
• 8:52
  SPEAKER_00: It may have been the democratization of workflows.
• 8:55
  SPEAKER_00: Now everybody can get in on the game that only the LinkedIn Jetsons lawyers seem to be playing.
• 9:03
  SPEAKER_00: And that's the development every lawyer should be watching.
• 9:07
  SPEAKER_00: This is Ron Drescher.
• 9:08
  SPEAKER_00: This is AI Tools for Practicing Lawyers, and we'll see you next time.