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Troubleshooting the Document Uploader

The Document Uploader lets users with access seamlessly upload documents directly within the main chat window. Below, you will find support, tips and tricks for using this tool.

Before you start: Chat History must be on

The Document Uploader only works when Chat History is enabled for your organisation. If Chat History is switched off, the upload option will not appear in the chat window and you will not be able to send documents to Nylon.

Chat History is enabled by default and is managed at the organisation level. Only an account Owner or Admin can change this setting, under Account → Settings → History & Feedback → History. If the uploader isn't appearing for you, ask an Owner or Admin to confirm Chat History is turned on.

For more on how Chat History works and what's stored, see Using Chat History.

Types of Documents

  • Doc format: Nylon can read:

    • Documents — PDF, DOCX, DOC, RTF

    • Spreadsheets & data — XLSX, XLSM, XLS, CSV, TSV

    • Email — .EML files, and email threads exported from Outlook as JSON

    • Plain text — TXT, MD and similar plain-text files

    Word documents (DOC/DOCX) read best when the content is mostly text. Files with heavy formatting, embedded objects or tracked changes may occasionally not read correctly — if one doesn't upload, try converting it to PDF.

  • Scanned documents are fine: Nylon runs OCR automatically, so you don't need to convert or process a scan before uploading it. See What Nylon can and can't read below.

  • Document Limit: You can upload a maximum of 20 documents at a time.

  • Language: Currently, we can only support documents using the Roman alphabet. If your document is not uploading, check that it doesn't contain any other characters.

  • Size Limit: Max size per document is 10MB on Starter and 50MB on Adviser and Elite. If your document is bigger than this try exporting only the relevant sections and uploading again.

What Nylon can and can't read

Nylon reads the words in your documents. Scanned and photographed files are fine — Nylon runs OCR (optical character recognition) on them automatically, so a scan reads just like a typed file.

Scans do need processing first, so they take longer than a typed file. Nylon works through the document a page at a time, so you'll see it progressing — a page or two is quick, and a long bundle can take a few minutes.

What Nylon can't do is interpret pictures. It will pick up text that appears inside an image, but it doesn't understand what the image is showing.

Reads well

  • A scanned PDF of a signed lease, deed of trust or settlement agreement.

  • A photo or scan of a rates notice, IRD letter or bank statement.

  • An old faxed or photocopied letter in a correspondence bundle.

  • A set of financial statements, whether typed or scanned.

Doesn't read

  • Charts and graphs — Nylon can read the labels on a revenue chart, but not the values the bars represent. Upload the underlying spreadsheet, or put the figures in your question.

  • Group structure and org charts — it reads the entity names in the boxes, but can't tell you who owns whom. Describe the structure in your question instead.

  • Site plans, floor plans and survey diagrams — these are treated as pictures, not read.

  • Tables pasted in as screenshots — the text may be picked up, but rows and columns can end up scrambled. Upload the spreadsheet or the original document where you can.

  • Handwriting — margin notes and handwritten amendments are unreliable. Typed text reads far better.

A page that is almost entirely image — a photograph, a full-page diagram, or a scan too faint to OCR — has little or no text for Nylon to read. If a document averages fewer than 20 words per page, it will fail to upload. Try uploading only the relevant sections.

Limitations

The Document Uploader feature includes the following functionalities:

  • Combines the context of your document with our database of case law, legislation and guidance.

  • Incorporates citations relevant to your document.

  • Remembers the conversation chain, allowing users to ask follow-up questions based on previous interactions.

  • You don't need to upload documents we already have e.g. a specific case or section of legislation.

  • New conversations don't have access to documents uploaded in previous conversations. Just like how our AI system does not train on your previous conversations, it also cannot access previously uploaded documents.

How can I upload email chains

You can upload email directly — either raw .eml files saved from your email client, or an email thread exported from Outlook as JSON. You can also export an email to PDF and upload that, or attach emails straight from your mailbox if your firm has the Outlook integration enabled (see Connecting Outlook to Nylon).

At this stage, it won't be able to adjust its writing style to match your tone, try providing prompt descriptions instead.

Data Security

Your privacy and data security are our top priorities. The following measures are in place to protect your documents:

  • Uploaded documents remain in your account and cannot be accessed by anyone else, including Nylon.

  • All documents will be permanently deleted from the system after 30 days of not being used. If you haven't been active in your conversation for more than 30 days, you will need to re-upload your document to continue a technical conversation.

Example Prompts

To maximise the utility of the Document Uploader, consider using the following prompts when interacting with the feature:

  • Create a one-paragraph client-facing summary of this contract, suitable for a non-lawyer.

  • Find all indemnity provisions in this contract and summarise how these relate to the current case law

  • List every statute cited in this court document, give the exact sections references and summarise whether that section has been repealed or amended.

  • For each cause of action pleaded in this Statement of Claim, list the legal tests, controlling authorities and leading cases. Identify any factual gaps in the pleadings.

What's next?

  • We are improving the system to handle your questions better, and more deeply understand the document you are uploading, including support for more complex Word document formatting over time.

We encourage users to explore the Document Uploader feature. Should you have any questions or require assistance, please do not hesitate to reach out to our support team. Click the Chatbot button at the bottom right to submit a support request and our team will get back to you as soon as we can!

Last updated: 26 August 2026

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