File Attachments

You can add files to Pia and have Pia read them as part of your message. This works in both the Assistant and Optimize views, and the two behave differently:

In the Assistant, an attached file becomes a chip beside the message box. The overlay while you drag reads “Drop files to attach them”.
In the Optimize view, a file’s text is inserted into the box you are about to optimize. The overlay there reads “Drop file to insert its contents”.

Adding a File

There are two ways to add a file:

Drag a file onto the Pia window and release it.
Click the Attach file button (paperclip) and pick a file.

You can add several. In the Assistant each one gets its own chip; in Optimize their contents are joined together, separated by a line. In Optimize, if the box already has text, a snackbar asks whether to Insert anyway.

Attachment chips in the Assistant

An attached file sits as a chip above the message box until you send, and the sent message keeps its chips — so what you attached is still visible when you come back to the chat later.

Each chip carries two buttons:

Save to the working directory copies the file into the chat’s working folder, where Pia’s file tools can reach it afterwards. Without saving, the file is read for that one message only and is not kept. A saved chip can be opened, or its containing folder revealed, later.
Remove file takes it off the message before you send.

A file staged in one chat does not follow you into the next one — switching chats clears what you had attached.

Supported file types

In the Assistant, you can add:

Plain text and code files — for example .txt, .md, .csv, .json, .xml, .yaml, .log, and source-code files like .cs, .js, .ts, .py, .html, .css, .sql
Word documents — .docx
Excel spreadsheets — .xlsx, .xlsm
PDFs — .pdf
Outlook and standard mail — .msg, .eml
Images — .png, .jpg, .gif, .bmp, .webp

The Optimize view supports the same file types, except images.

A PDF has its text read out the way a Word or Excel file does. A scanned PDF — one that is really a stack of pictures — says it holds no text rather than failing silently.

Dragging mail out of Outlook

Mail can be dragged straight out of Outlook’s message list, not only from a .msg file already saved to disk. Both .msg and .eml are read into text, so you can drop a mail into a chat and ask about it.

Images

An image attachment becomes a picture the AI provider looks at, and it needs the Pia Cloud provider. On any other provider — including an Anthropic or OpenAI provider you added with your own key — you’ll see “Image attachments are only available when using the PiaCloud provider.” See the AI Providers Guide to switch to Pia Cloud.

Up to four images on one message

A message can carry up to four images. Dropping, pasting or capturing another one adds it to a thumbnail strip above the message box rather than replacing what is already there, and each thumbnail has its own remove button.

Past four, the extra image is left out and Pia says which one: “At most 4 images can be attached — ‘X’ was left out.” Images are also held to a combined size budget, so a fifth large picture can be turned down before the count is reached.

Capturing your screen instead of attaching a file

The Capture screen button next to the paperclip opens a picker of your displays and open windows. The shot lands in the message box as a thumbnail and is sent only when you send the message. Pia’s own windows are never offered.

You can also open that picker on a shortcut of your own, set under Settings → General → Hotkeys, and it works while Pia is still answering — the picture waits in the message box for your next message.

Screen capture needs Pia Cloud for the same reason images do; on any other provider the button is greyed out and says so.

Asking about an image already in your files

Pia can also look at an image without you attaching it. Ask about a screenshot by name and the read_file tool shows Pia the picture instead of answering that you should attach it. Pia sees the image for one reply, so ask what you need from it in the same message. See Coding Tools & @Files.

How large a file can be

The limit is on how much text comes out of the file, not on the file on disk: roughly 1 MB of extracted text. That is a lot of writing — comfortably a few hundred pages of plain prose — so ordinary documents, logs and source files are never a problem.

Formats that hold their text compressed, like .docx and .xlsx, are allowed to be considerably larger on disk, because what matters is the text inside them. A spreadsheet with heavy formatting and a modest amount of text will usually go through; one with a million populated cells will not.

Over the limit, the file is refused and Pia names the limit it exceeded — “‘X’ is too large to attach — the limit is N MB.” Nothing is attached. Split the file, or paste in just the part you need.

What an attachment sends to your AI provider

An attached file does reach the AI provider. Attaching it doesn’t hand Pia a reference to something on disk — Pia reads the file and sends its whole text along with your message. In the Assistant the chip is what you see, not the text, but the text goes all the same; in Optimize it is pasted into the box in front of you. Either way it reaches whichever AI provider you’re using, exactly like anything you typed by hand.

So treat attaching a file as pasting it. If the contents are sensitive, the same considerations apply as for any other message:

Check what you attached before you send. Remove a chip you didn’t mean to include; in Optimize, the text is in the box and you can edit or delete any of it.
PII Tokenization (Settings → General → Privacy) replaces personal details with tokens before the request leaves your device, and applies to attached text like any other. See the Privacy guide.
Which provider receives it is whichever you’ve configured — a direct API key sends it straight to that vendor, Pia Cloud sends it to your Pia server. See AI Providers.

This is different from Pia’s file tools, where Pia reads files in your assistant folder on its own initiative and only the parts it actually opens are sent.

A Few Things to Know

Spreadsheets: each sheet becomes its own labelled block. Heads up — dates in spreadsheets may show up as plain numbers.

Next Steps

Learn more about where you’ll use attachments in the Assistant Guide and the Optimize Guide.