If Attach files says Choose one company to attach files, select the company whose document you want Max to read. The attachment picker does not combine files from an all-company view.
Open Attach a file again after selecting the company. The list contains eligible files already stored in that company’s Documents, subject to your current access.
Check the filename and the company before adding a file. A similarly named document in another company is not interchangeable. If the file exists only on your device, upload it through Documents first and confirm that upload succeeded.
Adding the file to the composer lets Max read it when you send your question and use it in that conversation. It is not a cross-company sharing action. If you switch company context, start with the appropriate conversation and attachment selection there rather than expecting a file from the earlier company to remain available under the new one.
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