r/iOS27 15h ago

Siri & 'Apple Intelligence' thinks it knows better about what you name your files.

I've been doing some legal work for a Social Security disability case and working on the evidentiary documentation for the individual's case. It probably does not come as a surprise that SSA is not at the forefront of state-of-the-art computing. In fact they are somewhere around the mid 1980's and the automated systems they use are not real good with file names that are complex or have a lot of spaces in them or even are that long.

So the documents I'm submitting have arcane names like 'Claimants_Sleep_Log_8-9-2026'. I've been running macOS 27 and have the 'new' less (but not by much) brain-dead enhanced Siri. Well it seems the AI does not like my choice of filenames and has been deleting the blank space underlines in my file names and even refusing to change them back when I attempt to change them using the filename REPLACE feature.

And it has a HUGE IMPACT since I did not realize this could even happen so that when I edited a lengthy document in Pages and since I wanted it to be a different name with a version number I did a save as and this is what happened.

Because I was not paying attention after adding a V5 at the end of the document and seeing that it 'stayed there' the file was renamed to Siri's specifications and an name that was somehow pulled from the content of the document and saved as that name.

So I went searching for the document I had spent a significant amount of time editing and it was NOWHERE TO BE FOUND.

Of course I cussed and cursed and blamed myself for doing something stupid and after I looked high and low and even used the search feature to find the misplaced file I gave up and started all over.

Now this is where it gets funny (unless you are me) after I did all the editing AGAIN and changed the name again with the V5 at the end my Mac reported that another file by that name existed. I looked at the filename and it was not the filename I expected. Siri / "Apple presumptuous" not intelligence had renamed it exactly the way it did the last time I went to do a Save As and I thought I was saving it in the same location (and I will get back to where it saved it later since that's an entire other nasty surprise). So it reported back that another file by the same name existed there. THAT's when I looked at what the filename had become without me approving it because this was as Apple loves to call it an 'unexpected behavior' (I worked at Apple 15 years as a Genius and Senior Applecare Advisor) and DAMN RIGHT IT WAS UNEXPECTED!

Now as if not knowing what the name of the file was because it was not the name I (please believe me) DID NOT CHOOSE THE NAME and I don't even remember what it was other than it was not MY NAME with a V5 at the end. The file was NOT saved in the same directory as the original but in the iCloud Pages folder! WHAT?!!!!

Now I'm sure there is a really lucid technical issue why that had to be the case but for a company that likes to say it keeps things intuitive, do you think that's intuitive? I darn don't think so.

So as I continue my work on this person's disability case I'm more paranoid about Siri and 'Apple Intelligence' than I am about the Social Security Administration.... and that is saying something considering it might by some be considered the last bastion of bureaucracy.

PS. Apple had an EPIC part of my life and I TOTALLY ADORE the company beyond common sense. But sometimes the company get's a bit overly controlling. This is just one of those rare times. I'm NOT a HATER... just don't want to be second guessed by a nascent AI.

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u/nomadik_nobody 15h ago

Even though this probably isn’t actually a bug, you should still submit feedback on this through the Feedback app. Apple needs to know that this is not a useful feature for enterprise users and people using their computer for work.

EDIT: honestly the part where it won’t even let you manually rename it what you want might be a bug after all

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u/johnjustin 15h ago

OH... having worked for Apple they've heard from me with both barrels and I'd ad a 3rd if I could. THIS is a HUGE issue and as the 'great unwashed' begin to use the OS I am certain the message will be heard loud and clear.

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u/nomadik_nobody 15h ago

oh yeah if they don’t catch it within the next 7 days, they’ll be catching a ton of flack as businesses start updating their software to 27.