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Ileen Docs

Uploading Files & Project Documents

Ileen lets you give agents extra context by uploading files. There are two distinct places files are used:

  1. Ephemeral chat attachments — added to a single message via the paperclip button in any chat.
  2. Project Documents — files persisted on the project and automatically injected as context in every agent call.

Attaching files in chat

Any chat window (Architect, Tech Leader, Code Query, Content Review, Deploy) has a paperclip button next to the message input.

  1. Click the paperclip — a file picker opens.
  2. Select one or more files.
  3. A preview row appears below the textarea:
    • Images show a thumbnail.
    • Text / code files and documents show a file-type icon.
    • Click × on any file to remove it before sending.
  4. Type your message and click Send. The files are included with that message only.

Supported file types

CategoryExtensions
Images.png, .jpg, .jpeg, .gif, .webp
Text / code.txt, .md, .html, .css, .js, .ts, .json, .py, .java, .c, .cpp, .h, .go, .rs, .yaml, .yml, .xml, .sql, .sh
Documents.pdf, .doc, .docx, .xls, .xlsx

Unsupported file types are skipped automatically with a warning — you won’t be blocked.

Project Documents — persistent context

When working in Content Mode, files uploaded in the Briefing step are saved as Project Documents. They stay attached to the project and are automatically injected as context in every future agent call for that project.

Open the Project Documents panel from the project sidebar to review them.

What’s in the panel

ColumnWhat it shows
IconImage / text-code / document icon based on type
FilenameOriginal name at upload time
Type badgeImage / JSON / Python / JS / HTML / CSS / Markdown / PDF / Word / Excel / Text
SizeHuman-readable (KB / MB)

Managing documents

  • Refresh — click the refresh icon in the panel header to re-fetch the list.
  • Delete — click the trash icon next to any document, confirm, and it’s removed. The document will no longer be used as context.
  • The footer shows the total count: “N documents • All injected as context”.

When to use which

Use caseUse
One-off: explain a screenshot, ask about a single PDFChat attachment
A brand guide that should influence every piece of contentProject Document (via briefing)
A specification PDF the architect needs for the plan onlyChat attachment
Company tone-of-voice sample filesProject Document