Have you asked the users for the type of attachment they are trying to upload (jpeg, png, gif, etc) and the width, height, and filesize of these attachments? Perhaps they are too large? Also, these server settings may also effect your attachment upload limits:
PHP Settings:
max_execution_time
memory_limit
post_max_size
upload_max_filesize
max_input_time
MySQL Settings:
max_allowed_packet
wait_timeout
What do you have set for these on the server? And have they changed recently?
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