Uploaded files to Portal server are corrupted

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I have an user "checked out" a file, modified it, and "save and check in" the
file.
When he tries to access the file again, it becomes corrupted.
Any reason why it is doing this?

He posted an older version to the portal server again, went through the
steps "check out, modify, and check in" , and it is happening again. Is it
file-specific? He seems to be ok with other files.
.

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