Siri File Search on Mac: What Works and What Doesn’t

What people mean when they say “search files with Siri”

Most people do not remember filenames and don't want to spend hours renaming files. They remember:

• A sentence they wrote

• A number in a spreadsheet

• A slide title

• A screenshot they took

• A phrase from a PDF

• A meeting moment in a recording

So the real need is not “open a file”, it is “find the moment inside the file”.

That is exactly where general assistants tend to break down.

What Siri will probably do well

Siri is a general assistant. On Mac, it usually performs best when:

• The request is simple and the target is obvious

• The file is easy to identify by name (at best !)

• The content lives in Apple-first surfaces (system apps and system-indexed content)

If your workflow is mostly first-party apps and you remember all your filenames, Siri can feel good enough.

Where Siri tends to fall short for real work files

Even with a major upgrade, Siri still has to operate inside Apple’s system boundaries and app integrations. That matters, because most work happens in mixed file types across many folders. Excel, Words, Powerpoint, Notion, Indesign etc..

Here are the common “Siri file search” gaps that show up in real workflows:

Searching inside content, not just filenames

You remember the paragraph, not the document name. You need search inside:

• PDFs

• Images

• Video

• Word documents

• Slide decks

• Notes and Markdown

• Spreadsheets and CSVs

Jumping to the exact spot

Even if an assistant can locate a file, it often cannot take you to:

• The right PDF page

• The right slide number

• The exact sentence in a long document

• The moment in an audio or video recording

Supporting the file types people actually use

Apple will always prioritize Apple surfaces. Many workflows rely on formats like:

• Word, PowerPoint, Excel, Keynote, Pages

• All type of images (RAW included)

• Markdown, JSON, Python script

• InDesign, Photoshop, Illustrator project files

If you live inside creative tools, data files, or long research documents, you will likely want a dedicated file search layer.

The simplest way to think about it

Siri is a general assistant for your Mac.

Fenn is a file intelligence layer for your Mac.

Siri helps you do things. Fenn helps you find things, especially the exact moment inside your files.

When you need reliable file search, use Fenn

Fenn is “Private AI that finds any file on your Mac.”

It is built for the way people actually search:

• You remember a snippet, not a filename

• You want the result instantly

• You need to open at the exact page, slide, or timestamp

• You cannot upload confidential work to a cloud tool

What Fenn does differently

• Searches inside your documents: PDFs, documents, screenshots, audio, and video

• Opens results at the exact moment, with contextual snippets (see screenshot below)

• Chat with your data 100% privately

• Runs on-device on Apple Silicon Macs, for privacy