A Max message can include up to four different files, with a combined size limit of 12 MB. The total applies across the selected attachments, not separately to each one.
Check the sizes shown in the picker and remove files that are not needed for the question. The same file cannot be selected twice, and an empty or invalid file will not satisfy validation.
If the combined size is too large, prepare a smaller supported version containing the relevant pages or material, upload it to Documents, and select that version. Preserve the information needed to answer the question rather than reducing the file so much that it loses context.
These limits differ from the general Documents upload limits. A file can be stored successfully in Documents yet be too large for a Max message. Confirm the selected files above the composer and write the question before sending. If validation still fails, use the specific error to distinguish a count, size, or format problem.
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