Can ChatGPT read Word documents?

What survives, and what does not

The one that matters is the images row, and it is the one nobody expects.

Images are dropped, silently

OpenAI's documentation is explicit. Visual retrieval for PDFs exists on ChatGPT Enterprise. On every other plan:

All other plans and document files only support text-based retrieval. This means that ChatGPT will extract digital text from the file and discard any images.

So a chart in your report is not there. A screenshot pasted into the document is not there. A diagram is not there.

When a Word file is too large

Nearly always images again, since text weighs almost nothing.

Saving as plain text routinely takes a document from tens of megabytes to tens of kilobytes. Given the images were going to be discarded regardless, you lose nothing ChatGPT would have used.

File, then Save As, then Plain Text. Ten seconds.

When it is too long rather than too large

A different problem with a similar feel, and converting does not help at all, because the words are the issue.

Text and document files are capped at 2 million tokens. Past that, the file uploads and ChatGPT reads part of it. No error appears.

Check with a question that can only be answered from the end:

What is the title of the final section?

If it cannot say, the rest was never read.

The fix is to send less at a time: the section you need, or the whole thing split into parts sent in order with an instruction to hold the answer until they have all arrived.

Getting more out of a Word upload

Use the headings. If the document has a real heading structure, ask for a section-by-section summary using the document's own headings. It also makes truncation obvious, since sections that vanish were never read.

Ask for quotes. Requiring the sentence behind each claim makes everything checkable and cuts paraphrase drift.

Clean up first if it is a mess. A document thick with tracked changes and comments gives ChatGPT a confusing picture. Accepting all changes on a copy before uploading tends to produce noticeably better answers.