Before buying an AI assistant that generates files, ask which formats it can create, where the file is built, where it is stored, who can open the link, and whether the output is checked for active content such as formulas or macros. File creation turns model text into something other programs execute or trust.
Why file generation deserves its own review
A chat answer is text on a screen. A generated file leaves the assistant and goes into your inbox, a shared drive or a customer's hands. It carries your company's name and may be opened by software that treats some content as instructions. OWASP describes improper output handling as insufficient validation, sanitization and handling of model outputs before they are passed downstream. A generated file is a downstream handoff.
Six areas to cover
1. Formats. List what the product can produce: documents, spreadsheets, slides, PDFs, images, archives, code files. Each format has its own risks. Ask whether macro enabled formats are ever created.
2. Where the file is built. Some products build files in a remote environment, others on your device. Ask where, and what that environment can reach while it builds.
3. Source data. Which of your files and connected sources can the assistant read to fill the file? Confirm it respects the user's access rather than a broader service account.
4. Storage and links. Where does the finished file live, and for how long? Is a download link public, private, or expiring? Can an admin see and delete generated files?
5. Sharing. Can a user share a generated file outside the company with one click? Can that be restricted by policy?
6. Content checks. Is the output scanned for spreadsheet formulas, embedded links, macros or scripts? Are there controls for sensitive data such as personal information appearing in a file?
A comparison worksheet
| Question | Answer to record | Evidence type |
|---|---|---|
| Formats created | List | Docs or test |
| Macro formats possible | Yes or no | Test |
| Build location | Device or cloud | Docs |
| Default link visibility | Private, org, public | Test |
| Retention of files | Duration, deletion method | Docs and contract |
| Admin visibility | Search, audit, delete | Console check |
| Formula or macro handling | Described behavior | Test |
| Source access model | User or service | Docs |
Mark each answer as tested, documented or claimed. Tested wins.
Run three quick tests
First, ask the assistant to make a spreadsheet containing a cell that begins with an equals sign, such as text from a pasted ticket. Open it in a spreadsheet program in a safe environment and see whether the cell behaves as a formula. Second, generate a file and inspect its link: open it in a private browser window without signing in. Third, delete a file as an admin and confirm it is gone from the link and from storage.
These tests take under an hour and answer questions a datasheet will not.
Content that should never be in a generated file
Agree rules before rollout. Typical ones: no secrets or credentials, no personal data beyond what the task needs, no customer data in files that leave the company unless approved. If the assistant can read a source holding such data, the file can contain it, so the control belongs at the source access level and not only at the output.
For related checks on spreadsheets and macros, see the posts on CSV injection in AI-generated spreadsheets and macros in AI-generated Office files.
Safeguard does not generate your documents, but its compliance and evidence automation can help you keep proof of the controls you set around these features.
A worked example: the customer renewal deck
A sales team wants the assistant to build a renewal slide deck from account notes and a usage export. Walk through the six areas.
- Formats: slides and PDF. The vendor confirms no macro formats are created.
- Where built: in the vendor's cloud, from files the user attaches, so the assistant sees only what the user shares.
- Source data: the usage export contains customer names and contact emails. That is personal data, so the team limits the export to what the slides need.
- Storage and links: the file is stored for a set period, and the link defaults to organization only. The team confirms with a test.
- Sharing: a user can create a public link. The admin turns that option off.
- Content checks: none for slides, so the team adds a human review step before anything leaves the company.
The outcome is not a yes or a no. It is a short list of settings changed and rules agreed, which took an afternoon.
Step by step: a trial script
- Pick two realistic tasks and one unrealistic one, such as a request for a macro file.
- Generate each file with a standard user account, not an admin account.
- Check the link in a private window.
- Open any spreadsheet safely and test a cell starting with an equals sign.
- As an admin, search for, view the access record of, and delete one file.
- Record answers in the worksheet above with an evidence level.
What goes wrong in practice
Teams most often hit three issues. First, a link that is more open than assumed, because the default was set for convenience. Second, personal data in a file because the source export was broader than needed. Third, no one knows how long files are kept, so a retention question during an audit has no answer. All three show up in a trial if you look for them, and all three are cheaper to fix before rollout.
Pair it with the access model
File generation is only as safe as the sources the assistant can read. Review it together with connector access. A narrow source scope plus private links plus a short retention window gives a defensible posture. A broad source scope with public links does not, however good the output checks are.
Try it yourself
Click through it at your own pace, or open it full screen. Look at how controls map to evidence, and which records you would keep for your own review.
Quick check
Is a generated PDF safer than a generated spreadsheet?
Generally it carries less active content, but links, embedded files and sensitive data can still be present. Check each format you allow.
Who owns generated files in the product?
Ask the vendor for storage, retention and deletion terms in writing, and confirm admins can see and remove files.
Do we need a separate policy for generated files?
Often an addition to your existing data handling policy is enough: allowed formats, link defaults, retention and review before external sharing.
Sources
Last reviewed: 19 October 2026.
