Siri AI keep saying 'I’m having trouble with the connection' on my MacBook Pro M4

My MacBook Pro M4 has all the right settings to use Apple's new Siri AI, and the software is fully installed. However, every time I try to use it, Siri keeps saying "I’m having trouble with the connection. Please try again later." The only prompts that worked were simple ones like "Hi or "What time is it".


  • Cleared my iCloud storage
  • Turned off and on Siri AI multiple times
  • Restarted my MacBook multiple times
  • Apple Account region is in Taiwan, which I believe is available
  • Has been accepted on the waitlist, and installed the new Siri AI
  • Language is set to English (United States)




[Edited by Moderator]

Original Title: My MacBook Pro M4 has all the right settings to use Apple's new Siri AI, and the software is fully installed. However, every time I try to use it, Siri keeps saying "I’m having trouble with the connection. Please try again later."

MacBook Pro 14″, macOS 27.0

Posted on Sep 21, 2026 4:53 PM

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Question marked as Top-ranking reply

Posted on Sep 28, 2026 5:29 PM

Apple released macOS 27.0.1, which fixes this issue. Early tests show the fix works; the update solved the problem on my system after installation.

31 replies

Oct 1, 2026 7:57 AM in response to ronlovemich

Well this morning I was getting set up for my call from Apple Support, opened the MacBook and like magic Siri AI was working as it should, I missed the call and spoke with another but they were like ok cool.

The only thing I did was leave it plugged in since Tuesday night. I did update my Studio and it updated with zero issues.

So maybe the Matrix actual exists. LOL

Oct 3, 2026 8:59 AM in response to ronlovemich

Updating to 27.0.1 had no effect for me. I've tried prompting Siri AI every day since macOS 27 released, and it's only succeeded twice. Changing networks, toggling VPN, etc. seems to have no effect.


My iPhone sees more success—Siri prompts fail maybe 15% of the time, although that's still an unacceptable rate.


I'm noticing that I get a mild feeling of dread whenever I think to ask Siri something, because these past two weeks have had me develop a strictly negative association with it.

Siri AI keep saying 'I’m having trouble with the connection' on my MacBook Pro M4

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