File Uploads to Chat

Attach a document, spreadsheet, PDF, or image straight into a chat message and your employee reads it as part of the conversation, no separate upload step and no waiting for processing. Images, PDFs, Office files (Word, Excel, PowerPoint, and their legacy and OpenDocument equivalents), plain text, CSV, JSON, and XML are all accepted. Every attachment lands in that employee's Drive under Uploads so it is easy to find again later.

When you are talking to an AI employee and the conversation needs a real document behind it, you do not leave the chat to go find an upload form. You drag the file in, or attach it from the message box, and send it along with your message. The employee reads it the same turn: a spreadsheet of numbers to check, a PDF contract to summarize, a screenshot of a bug, a logo to use in a deck.

Up to five files can ride on a single message, each capped at 72 MB, with the same ceiling applying to the combined size of everything in that message. The system checks the real bytes of each file, not the filename extension or the label the browser sends, so a renamed file cannot slip past the allow list. Accepted formats span images (JPEG, PNG, GIF, WebP, SVG, BMP, TIFF), PDFs, plain text, Markdown, CSV, JSON, XML, and the full Office and OpenDocument document, spreadsheet, and presentation families.

The distinction that matters here is what an attachment is versus what happens to it afterward. File Uploads is the delivery mechanic: getting a file from your machine into the conversation, validated, sized, and stored, in one step, without a separate Drive visit first. Reading the contents, whether that is pulling text out of a PDF, parsing a spreadsheet, or describing an image, is a different capability the employee applies once the file has arrived. Keeping upload and reading separate is why a 40-page contract and a screenshot both attach the same way, even though what the employee does with each is completely different.

What You Can Attach

Images (JPEG, PNG, GIF, WebP, SVG, BMP, TIFF), PDFs, plain text, Markdown, CSV, JSON, and XML all attach directly. The full Office family, Word, Excel, and PowerPoint, plus their legacy .doc/.xls/.ppt and OpenDocument .odt/.ods/.odp equivalents and RTF, is also accepted, so a contract from a client or a spreadsheet from a teammate does not need converting first.

Each message can carry up to five attachments, and each file tops out at 72 MB, with the same 72 MB ceiling applying to everything in the message combined. That ceiling is set by what a single web request can carry end to end, not an arbitrary product choice, so it is the same limit whether you attach one large file or several smaller ones.

Monthly Limits by Plan

Chat attachments use both your shared workspace storage allowance and a separate monthly attachment-count limit. Free includes 10 attached files a month; paid plans scale from 200 a month up through 2,000 a month on the Agency tier, and custom plans lift the cap entirely. The counter resets on the first of each month.

The count is separate from your persistent storage allowance in gigabytes, which covers every file across the platform, not just chat attachments. You could be well under your storage cap and still hit the monthly attachment count if you are sending a high volume of small files, and the reverse is also possible with a few very large ones.

How It Works

Attach a file to a message, and it is validated, stored, and ready before the employee replies

Attaching a file adds it to the message you are about to send. The file's real content, not its extension, is checked against an allow list of accepted formats. Anything outside that list, or over the size ceiling, is rejected before it is ever stored, with a clear reason shown in chat.

Once accepted, the file is written to your workspace's storage and linked to that message and to the employee's Drive at the same time, filed under Uploads so it shows up in both places: the conversation where you sent it, and the Drive folder where every file that employee has touched lives. From there the employee can open, read, or act on it as part of answering you.

Use Cases

Get a contract or proposal reviewed

Attach the PDF straight into your message and ask your employee to summarize the terms, flag anything unusual, or compare it against a previous version, without leaving the conversation to upload it somewhere first.

Hand off a spreadsheet for analysis

Drop in a CSV or Excel export of sales, expenses, or usage data and ask for totals, trends, or a cleaned-up version back, the same way you would hand a colleague a file across a desk.

Show, don't describe, a bug or design issue

Attach a screenshot of an error message or a rough mockup image so the employee can see exactly what you mean instead of working from a text description alone.

Bring outside reference material into a task

Attach a brand guideline document, a past report, or a partner's brief so the employee's next piece of work matches what you already have on file.

FAQ

What file types can I attach in chat?

Images (JPEG, PNG, GIF, WebP, SVG, BMP, TIFF), PDFs, plain text, Markdown, CSV, JSON, XML, and the Office and OpenDocument document, spreadsheet, and presentation formats, including the legacy .doc/.xls/.ppt versions and RTF.

Is there a size limit?

Yes. Each file is capped at 72 MB, and the total across all attachments on one message is also capped at 72 MB. You can send up to five attachments per message.

Do attached files count against my Drive storage, or something separate?

Both. They count toward your persistent workspace storage allowance in gigabytes and toward a separate monthly count limit just for chat attachments, from 10 files a month on Free up to 2,000 a month on Agency, unlimited on custom plans. Only the attachment-count limit resets on the 1st of the month.

Where do the files go after I send them?

Every attachment is saved to the employee's Drive under Uploads / Chat, alongside anything the employee wrote or generated itself, so you can find it again without scrolling back through the conversation.

Can I attach a renamed or disguised file to get around the format restriction?

No. The file's actual content is checked, not its filename or extension, so relabeling a file to look like an allowed type does not let it through.

Where File Uploads to Chat fits

File Uploads to Chat is part of Where their work lives.

Your AI agents manage their own workspace. Scheduled tasks run daily, weekly, or on custom cron cadences. A built-in kanban board tracks what is in progress. Every document lands in a personal Drive. A daily work journal logs decisions, outcomes, and next steps automatically.

Where their work lives: Where your employees organize their work.

Read the guide

Guide: File Uploads to Chat

More in Workspace

Move a Team Member to the Bench: Every workspace has one Bench: a holding area for employees who are not currently on a working team. Remove someone from a team, or delete the team itself, and they land back on the Bench automatically, fully intact and ready to be reassigned. Nothing about them is deleted; only their team membership changes.
Task Board: A kanban board that tracks what every AI employee is working on, in Backlog, To Do, In Progress, and Done columns. Employees create their own task cards when they do real work, and you can create cards to assign work directly. View it per employee, per team, or company-wide, and it updates live as work moves.
Set Your Employee's Working Hours: Set how often each employee checks its board and acts on its own, from every 5 minutes up to monthly, without you asking each time. New hires start with a default hourly check-in that you can tighten, stretch, or turn into a specific daily time. The employee pauses itself automatically when there is nothing to do, it is onboarding, or credits run out, and picks back up on its own once that clears.
Work Journal: Every employee keeps a dated journal of what it did, decided, and got stuck on, written as it works, not after the fact. Open it from the employee's, team's, or organization's Drive tab to see a day's entries without reading the chat transcript. Entries carry a category (task completed, observation, decision, blocker, learning, or handoff) so you can scan for what changed. It starts on hire with nothing to configure.
Task Comments: Comment directly on a task, Drive file, sprint, CRM contact, or notification, and @mention the person, team, or AI employee who should act on it. The mention lands as a bell notification for a person or a direct work request for an employee, both replying in the same thread. Turn any comment into a tracked task in one click, so feedback never gets lost in a side channel.
CRM: Every business runs on a CRM, the shared book of the people and companies it deals with. Sistava builds one in, and your AI employees run it for you. They add a prospect the moment one comes up, keep contacts current, open deals and move them down the pipeline as they progress, and write notes so nothing is forgotten. You get one clean place to see who you know, what's in flight, and what it's worth, without paying for a separate CRM.
Sales Pipeline: Your deals live on a pipeline board, the same shape as your task board: a column for every stage, New, Screening, Meeting, Proposal, Customer, and a card for each deal showing its value and the company behind it. As a deal gets closer to won, it moves down the board. Your AI employees keep the pipeline current, opening deals, moving stages, and updating amounts, so you always know what's in flight and what it's worth, at a glance.
Let Your Employee Use Any Desktop App: Your employee controls your actual desktop, not just a browser tab. It clicks, types, manages files, and runs terminal commands in real applications on your machine, the same way you would sitting at the keyboard. It works through the free Desktop Companion app and covers native software, file management, and shell tasks in one capability.
Let Your Employee Work with Local Files: Connect the Desktop Companion app and your employee can read, write, list, and search files on your own computer, scoped to your home directory. Ask it to open a config, tidy a folder, or find every CSV in a project, and it works the files directly instead of asking you to paste their contents into chat.
Let Your Employee Run Terminal Commands: Once you pair the Sista desktop app, your employee can run real shell commands on your machine: git, npm, brew, ls, grep, and anything else you'd type yourself. Commands run as your own user with no privilege escalation, and a hard-coded blocklist rejects destructive patterns like rm -rf /, disk formatting, or piping a remote script into a shell before they ever execute.
Let Your Employee See Your Screen: Your employee looks at your actual screen and works from what it sees, not just an API. It captures your desktop through the Sista desktop app, reads the pixels the same way you would, and can click, type, and scroll based on what it finds. That covers any app you have open, including native software, dashboards, and design tools that never had an integration.
Employee Drive: Every document, generated image, video, screenshot, and daily work log an employee produces lands automatically in its Drive, no saving required. Browse it per employee, per team, or company-wide, as a searchable flat grid or as folders. Files preview inline, from PDFs and spreadsheets to code and video, so you rarely need to download something just to read it. Every update becomes a numbered version that you can preview or restore without losing the original file.